fix: tests after rebase

Bump actions/dependency-review-action from 4.3.5 to 4.4.0

.cirrus.yml

@@ -1,23 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: MIT
-
-freebsd_task:
-  name: FreeBSD
-
-  matrix:
-    - name: FreeBSD 13.3
-      freebsd_instance:
-        image_family: freebsd-13-3
-    - name: FreeBSD 14.0
-      freebsd_instance:
-        image_family: freebsd-14-0
-
-  env:
-    TEST_SKIP_SENDMAIL: 1
-
-  pkginstall_script:
-    - pkg install -y go
-
-  test_script:
-    - go test -race -cover -shuffle=on ./...

.github/workflows/ci.yml

@@ -0,0 +1,221 @@
+# SPDX-FileCopyrightText: 2024 The go-mail Authors
+#
+# SPDX-License-Identifier: MIT
+
+name: CI
+
+permissions:
+  contents: read
+
+on:
+  push:
+    branches:
+      - main
+  pull_request:
+    branches:
+      - main
+
+concurrency:
+  group: ${{ github.workflow }}-${{ github.ref_name }}
+
+jobs:
+    codecov:
+        name: Test with Codecov coverage (${{ matrix.os }} / ${{ matrix.go }})
+        runs-on: ${{ matrix.os }}
+        concurrency:
+            group: ci-codecov-${{ matrix.os }}-${{ matrix.go }}
+            cancel-in-progress: true
+        strategy:
+            matrix:
+                os: [ubuntu-latest]
+                go: ['1.23']
+        env:
+            PERFORM_ONLINE_TEST: ${{ vars.PERFORM_ONLINE_TEST }}
+            PERFORM_UNIX_OPEN_WRITE_TESTS: ${{ vars.PERFORM_UNIX_OPEN_WRITE_TESTS }}
+            PERFORM_SENDMAIL_TESTS: ${{ vars.PERFORM_SENDMAIL_TESTS }}
+            TEST_HOST: ${{ secrets.TEST_HOST }}
+            TEST_USER: ${{ secrets.TEST_USER }}
+            TEST_PASS: ${{ secrets.TEST_PASS }}
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: Setup go
+              uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+              with:
+                  go-version: ${{ matrix.go }}
+                  check-latest: true
+            - name: Install sendmail
+              run: |
+                sudo apt-get -y update >/dev/null && sudo apt-get -y upgrade >/dev/null && sudo DEBIAN_FRONTEND=noninteractive apt-get -y install nullmailer >/dev/null && which sendmail
+            - name: Run go test
+              if: success()
+              run: |
+                go test -race -shuffle=on --coverprofile=coverage.coverprofile --covermode=atomic ./...
+            - name: Upload coverage to Codecov
+              if: success()
+              uses: codecov/codecov-action@b9fd7d16f6d7d1b5d2bec1a2887e65ceed900238 # v4.6.0
+              with:
+                  token: ${{ secrets.CODECOV_TOKEN }} # not required for public repos
+    lint:
+        name: golangci-lint (${{ matrix.go }})
+        runs-on: ubuntu-latest
+        concurrency:
+            group: ci-lint-${{ matrix.go }}
+            cancel-in-progress: true
+        strategy:
+            matrix:
+                go: ['1.23']
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Setup go
+              uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+              with:
+                  go-version: ${{ matrix.go }}
+                  check-latest: true
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: golangci-lint
+              uses: golangci/golangci-lint-action@971e284b6050e8a5849b72094c50ab08da042db8 # v6.1.1
+              with:
+                  version: latest
+    dependency-review:
+        name: Dependency review
+        runs-on: ubuntu-latest
+        concurrency:
+            group: ci-dependency-review
+            cancel-in-progress: true
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: 'Dependency Review'
+              uses: actions/dependency-review-action@4081bf99e2866ebe428fc0477b69eb4fcda7220a # v4.4.0
+              with:
+                  base-ref: ${{ github.event.pull_request.base.sha || 'main' }}
+                  head-ref: ${{ github.event.pull_request.head.sha || github.ref }}
+    govulncheck:
+        name: Go vulnerabilities check
+        runs-on: ubuntu-latest
+        concurrency:
+            group: ci-govulncheck
+            cancel-in-progress: true
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Run govulncheck
+              uses: golang/govulncheck-action@b625fbe08f3bccbe446d94fbf87fcc875a4f50ee # v1.0.4
+    test:
+        name: Test (${{ matrix.os }} / ${{ matrix.go }})
+        runs-on: ${{ matrix.os }}
+        concurrency:
+            group: ci-test-${{ matrix.os }}-${{ matrix.go }}
+            cancel-in-progress: true
+        strategy:
+            matrix:
+                os: [ubuntu-latest, macos-latest, windows-latest]
+                go: ['1.19', '1.20', '1.21', '1.22', '1.23']
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: Setup go
+              uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+              with:
+                  go-version: ${{ matrix.go }}
+            - name: Run go test
+              run: |
+                go test -race -shuffle=on ./...
+    test-fbsd:
+        name: Test on FreeBSD ${{ matrix.osver }}
+        runs-on: ubuntu-latest
+        concurrency:
+            group: ci-test-freebsd-${{ matrix.osver }}
+            cancel-in-progress: true
+        strategy:
+            matrix:
+                osver: ['14.1', '14.0', 13.4']
+        steps:
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: Run go test on FreeBSD
+              uses: vmactions/freebsd-vm@v1
+              with:
+                  usesh: true
+                  copyback: false
+                  prepare: |
+                    pkg install -y go
+                  run: |
+                    cd $GITHUB_WORKSPACE;
+                    go test -race -shuffle=on ./...
+    reuse:
+        name: REUSE Compliance Check
+        runs-on: ubuntu-latest
+        concurrency:
+            group: ci-reuse
+            cancel-in-progress: true
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: REUSE Compliance Check
+              uses: fsfe/reuse-action@3ae3c6bdf1257ab19397fab11fd3312144692083 # v4.0.0
+    sonarqube:
+        name: Test with SonarQube review (${{ matrix.os }} / ${{ matrix.go }})
+        runs-on: ${{ matrix.os }}
+        concurrency:
+            group: ci-codecov-${{ matrix.go }}
+            cancel-in-progress: true
+        strategy:
+            matrix:
+                os: [ubuntu-latest]
+                go: ['1.23']
+        env:
+            PERFORM_ONLINE_TEST: ${{ vars.PERFORM_ONLINE_TEST }}
+            TEST_HOST: ${{ secrets.TEST_HOST }}
+            TEST_USER: ${{ secrets.TEST_USER }}
+            TEST_PASS: ${{ secrets.TEST_PASS }}
+        steps:
+            - name: Harden Runner
+              uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
+              with:
+                  egress-policy: audit
+            - name: Checkout Code
+              uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
+            - name: Setup go
+              uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+              with:
+                  go-version: ${{ matrix.go }}
+                  check-latest: true
+            - name: Run go test
+              run: |
+                go test -shuffle=on -race --coverprofile=./cov.out ./...
+            - name: SonarQube scan
+              uses: sonarsource/sonarqube-scan-action@884b79409bbd464b2a59edc326a4b77dc56b2195 # master
+              if: success()
+              env:
+                  SONAR_TOKEN: ${{ secrets.SONAR_TOKEN }}
+                  SONAR_HOST_URL: ${{ secrets.SONAR_HOST_URL }}
+            - name: SonarQube quality gate
+              uses: sonarsource/sonarqube-quality-gate-action@8406f4f1edaffef38e9fb9c53eb292fc1d7684fa # master
+              timeout-minutes: 5
+              env:
+                  SONAR_TOKEN: ${{ secrets.SONAR_TOKEN }}
+                  SONAR_HOST_URL: ${{ secrets.SONAR_HOST_URL }}

.github/workflows/codecov.yml

@@ -1,67 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: CC0-1.0
-
-name: Codecov workflow
-on:
-  push:
-    branches:
-      - main
-    paths:
-      - '**.go'
-      - 'go.*'
-      - '.github/workflows/codecov.yml'
-      - 'codecov.yml'
-  pull_request:
-    branches:
-      - main
-    paths:
-      - '**.go'
-      - 'go.*'
-      - '.github/workflows/codecov.yml'
-      - 'codecov.yml'
-env:
-  TEST_HOST: ${{ secrets.TEST_HOST }}
-  TEST_FROM: ${{ secrets.TEST_USER }}
-  TEST_ALLOW_SEND: "1"
-  TEST_SMTPAUTH_USER: ${{ secrets.TEST_USER }}
-  TEST_SMTPAUTH_PASS: ${{ secrets.TEST_PASS }}
-  TEST_SMTPAUTH_TYPE: "LOGIN"
-  TEST_ONLINE_SCRAM: "1"
-  TEST_HOST_SCRAM: ${{ secrets.TEST_HOST_SCRAM }}
-  TEST_USER_SCRAM: ${{ secrets.TEST_USER_SCRAM }}
-  TEST_PASS_SCRAM: ${{ secrets.TEST_PASS_SCRAM }}
-permissions:
-  contents: read
-
-jobs:
-  run:
-    runs-on: ${{ matrix.os }}
-    strategy:
-      matrix:
-        os: [ubuntu-latest, macos-latest, windows-latest]
-        go: ['1.23']
-    steps:
-    - name: Harden Runner
-      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-      with:
-        egress-policy: audit
-
-    - name: Checkout Code
-      uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
-    - name: Setup go
-      uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
-      with:
-        go-version: ${{ matrix.go }}
-    - name: Install sendmail
-      if: matrix.go == '1.23' && matrix.os == 'ubuntu-latest'
-      run: |
-        sudo apt-get -y install sendmail; which sendmail
-    - name: Run Tests
-      run: |
-        go test -race --coverprofile=coverage.coverprofile --covermode=atomic ./...
-    - name: Upload coverage to Codecov
-      if: success() && matrix.go == '1.23' && matrix.os == 'ubuntu-latest'
-      uses: codecov/codecov-action@b9fd7d16f6d7d1b5d2bec1a2887e65ceed900238 # v4.6.0
-      with:
-        token: ${{ secrets.CODECOV_TOKEN }} # not required for public repos

.github/workflows/codeql-analysis.yml

@@ -54,7 +54,7 @@ jobs:
 
     # Initializes the CodeQL tools for scanning.
     - name: Initialize CodeQL
-      uses: github/codeql-action/init@c36620d31ac7c881962c3d9dd939c40ec9434f2b # v3.26.12
+      uses: github/codeql-action/init@662472033e021d55d94146f66f6058822b0b39fd # v3.27.0
       with:
         languages: ${{ matrix.language }}
         # If you wish to specify custom queries, you can do so here or in a config file.
@@ -65,7 +65,7 @@ jobs:
     # Autobuild attempts to build any compiled languages  (C/C++, C#, or Java).
     # If this step fails, then you should remove it and run the build manually (see below)
     - name: Autobuild
-      uses: github/codeql-action/autobuild@c36620d31ac7c881962c3d9dd939c40ec9434f2b # v3.26.12
+      uses: github/codeql-action/autobuild@662472033e021d55d94146f66f6058822b0b39fd # v3.27.0
 
     # ℹ️ Command-line programs to run using the OS shell.
     # 📚 https://git.io/JvXDl
@@ -79,4 +79,4 @@ jobs:
     #   make release
 
     - name: Perform CodeQL Analysis
-      uses: github/codeql-action/analyze@c36620d31ac7c881962c3d9dd939c40ec9434f2b # v3.26.12
+      uses: github/codeql-action/analyze@662472033e021d55d94146f66f6058822b0b39fd # v3.27.0

.github/workflows/dependency-review.yml

@@ -1,31 +0,0 @@
-# SPDX-FileCopyrightText: 2022-2023 The go-mail Authors
-#
-# SPDX-License-Identifier: CC0-1.0
-
-# Dependency Review Action
-#
-# This Action will scan dependency manifest files that change as part of a Pull Request,
-# surfacing known-vulnerable versions of the packages declared or updated in the PR.
-# Once installed, if the workflow run is marked as required,
-# PRs introducing known-vulnerable packages will be blocked from merging.
-#
-# Source repository: https://github.com/actions/dependency-review-action
-name: 'Dependency Review'
-on: [pull_request]
-
-permissions:
-  contents: read
-
-jobs:
-  dependency-review:
-    runs-on: ubuntu-latest
-    steps:
-      - name: Harden Runner
-        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-        with:
-          egress-policy: audit
-
-      - name: 'Checkout Repository'
-        uses: actions/checkout@f43a0e5ff2bd294095638e18286ca9a3d1956744 # v3.6.0
-      - name: 'Dependency Review'
-        uses: actions/dependency-review-action@5a2ce3f5b92ee19cbb1541a4984c76d921601d7c # v4.3.4

.github/workflows/golangci-lint.yml

@@ -1,54 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: CC0-1.0
-
-name: golangci-lint
-on:
-  push:
-    tags:
-      - v*
-    branches:
-      - main
-  pull_request:
-permissions:
-  contents: read
-  # Optional: allow read access to pull request. Use with `only-new-issues` option.
-  # pull-requests: read
-jobs:
-  golangci:
-    name: lint
-    runs-on: ubuntu-latest
-    steps:
-      - name: Harden Runner
-        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-        with:
-          egress-policy: audit
-
-      - uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
-        with:
-          go-version: '1.23'
-      - uses: actions/checkout@f43a0e5ff2bd294095638e18286ca9a3d1956744 # v3.6.0
-      - name: golangci-lint
-        uses: golangci/golangci-lint-action@971e284b6050e8a5849b72094c50ab08da042db8 # v6.1.1
-        with:
-          # Optional: version of golangci-lint to use in form of v1.2 or v1.2.3 or `latest` to use the latest version
-          version: latest
-
-          # Optional: working directory, useful for monorepos
-          # working-directory: somedir
-
-          # Optional: golangci-lint command line arguments.
-          # args: --issues-exit-code=0
-
-          # Optional: show only new issues if it's a pull request. The default value is `false`.
-          # only-new-issues: true
-
-          # Optional: if set to true then the all caching functionality will be complete disabled,
-          #           takes precedence over all other caching options.
-          # skip-cache: true
-
-          # Optional: if set to true then the action don't cache or restore ~/go/pkg.
-          # skip-pkg-cache: true
-
-          # Optional: if set to true then the action don't cache or restore ~/.cache/go-build.
-          # skip-build-cache: true

.github/workflows/govulncheck.yml

@@ -1,21 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: CC0-1.0
-
-name: Govulncheck Security Scan
-
-on: [push, pull_request]
-
-permissions:
-  contents: read
-
-jobs:
-  test:
-    runs-on: ubuntu-latest
-    steps: 
-    - name: Harden Runner
-      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-      with:
-        egress-policy: audit
-    - name: Run govulncheck
-      uses: golang/govulncheck-action@b625fbe08f3bccbe446d94fbf87fcc875a4f50ee # v1.0.4

.github/workflows/offline-tests.yml

@@ -1,45 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: CC0-1.0
-
-name: Offline tests workflow
-on:
-  push:
-    branches:
-      - main
-    paths:
-      - '**.go'
-      - 'go.*'
-      - '.github/workflows/offline-tests.yml'
-  pull_request:
-    branches:
-      - main
-    paths:
-      - '**.go'
-      - 'go.*'
-      - '.github/workflows/offline-tests.yml'
-permissions:
-  contents: read
-
-jobs:
-  run:
-    runs-on: ${{ matrix.os }}
-    strategy:
-      matrix:
-        os: [ubuntu-latest, macos-latest, windows-latest]
-        go: ['1.19', '1.20', '1.21', '1.22', '1.23']
-    steps:
-    - name: Harden Runner
-      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-      with:
-        egress-policy: audit
-
-    - name: Checkout Code
-      uses: actions/checkout@61b9e3751b92087fd0b06925ba6dd6314e06f089 # master
-    - name: Setup go
-      uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
-      with:
-        go-version: ${{ matrix.go }}
-    - name: Run Tests
-      run: |
-        go test -race -shuffle=on ./...

.github/workflows/reuse.yml

@@ -1,23 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: CC0-1.0
-
-name: REUSE Compliance Check
-
-on: [push, pull_request]
-
-permissions:
-  contents: read
-
-jobs:
-  test:
-    runs-on: ubuntu-latest
-    steps: 
-    - name: Harden Runner
-      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-      with:
-        egress-policy: audit
-
-    - uses: actions/checkout@ee0669bd1cc54295c223e0bb666b733df41de1c5 # v2.7.0
-    - name: REUSE Compliance Check
-      uses: fsfe/reuse-action@3ae3c6bdf1257ab19397fab11fd3312144692083 # v4.0.0

.github/workflows/scorecards.yml

@@ -67,7 +67,7 @@ jobs:
       # Upload the results as artifacts (optional). Commenting out will disable uploads of run results in SARIF
       # format to the repository Actions tab.
       - name: "Upload artifact"
-        uses: actions/upload-artifact@604373da6381bf24206979c74d06a550515601b9 # v4.4.1
+        uses: actions/upload-artifact@b4b15b8c7c6ac21ea08fcf65892d2ee8f75cf882 # v4.4.3
         with:
           name: SARIF file
           path: results.sarif
@@ -75,6 +75,6 @@ jobs:
 
       # Upload the results to GitHub's code scanning dashboard.
       - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@c36620d31ac7c881962c3d9dd939c40ec9434f2b # v3.26.12
+        uses: github/codeql-action/upload-sarif@662472033e021d55d94146f66f6058822b0b39fd # v3.27.0
         with:
           sarif_file: results.sarif

.github/workflows/sonarqube.yml

@@ -1,56 +0,0 @@
-# SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
-#
-# SPDX-License-Identifier: CC0-1.0
-
-name: SonarQube
-
-permissions:
-  contents: read
-
-on:
-  push:
-    branches:
-      - main
-    paths:
-      - '**.go'
-      - 'go.*'
-      - '.github/workflows/sonarqube.yml'
-  pull_request:
-    branches:
-      - main
-    paths:
-      - '**.go'
-      - 'go.*'
-      - '.github/workflows/sonarqube.yml'
-jobs:
-  build:
-    name: Build
-    runs-on: ubuntu-latest
-    steps:
-      - name: Harden Runner
-        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
-        with:
-          egress-policy: audit
-
-      - uses: actions/checkout@ee0669bd1cc54295c223e0bb666b733df41de1c5 # v2.7.0
-        with:
-          fetch-depth: 0
-          
-      - name: Setup Go
-        uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
-        with:
-          go-version: '1.23'
-          
-      - name: Run unit Tests
-        run: |
-          go test -shuffle=on -race --coverprofile=./cov.out ./...
-
-      - uses: sonarsource/sonarqube-scan-action@884b79409bbd464b2a59edc326a4b77dc56b2195 # master
-        env:
-          SONAR_TOKEN: ${{ secrets.SONAR_TOKEN }}
-          SONAR_HOST_URL: ${{ secrets.SONAR_HOST_URL }}
-          
-      - uses: sonarsource/sonarqube-quality-gate-action@dc2f7b0dd95544cd550de3028f89193576e958b9 # master
-        timeout-minutes: 5
-        env:
-          SONAR_TOKEN: ${{ secrets.SONAR_TOKEN }}

.gitignore

@@ -56,4 +56,6 @@ crashlytics.properties
 crashlytics-build.properties
 fabric.properties
 
-testdata
+## Coverage data
+coverage.coverprofile
+coverage.html

auth.go

@@ -4,7 +4,11 @@
 
 package mail
 
-import "errors"
+import (
+	"errors"
+	"fmt"
+	"strings"
+)
 
 // SMTPAuthType is a type wrapper for a string type. It represents the type of SMTP authentication
 // mechanism to be used.
@@ -35,7 +39,7 @@ const (
 	// IETF draft. The IETF draft is more lax than the MS spec, therefore we follow the I-D, which
 	// automatically matches the MS spec.
 	//
-	// Since the "LOGIN" SASL authentication mechansim transmits the username and password in
+	// Since the "LOGIN" SASL authentication mechanism transmits the username and password in
 	// plaintext over the internet connection, we only allow this mechanism over a TLS secured
 	// connection.
 	//
@@ -44,20 +48,53 @@ const (
 	// https://datatracker.ietf.org/doc/html/draft-murchison-sasl-login-00
 	SMTPAuthLogin SMTPAuthType = "LOGIN"
 
+	// SMTPAuthLoginNoEnc is the "LOGIN" SASL authentication mechanism. This authentication mechanism
+	// does not have an official RFC that could be followed. There is a spec by Microsoft and an
+	// IETF draft. The IETF draft is more lax than the MS spec, therefore we follow the I-D, which
+	// automatically matches the MS spec.
+	//
+	// Since the "LOGIN" SASL authentication mechanism transmits the username and password in
+	// plaintext over the internet connection, by default we only allow this mechanism over
+	// a TLS secured connection. This authentiation mechanism overrides this default and will
+	// allow LOGIN authentication via an unencrypted channel. This can be useful if the
+	// connection has already been secured in a different way (e. g. a SSH tunnel)
+	//
+	// Note: Use this authentication method with caution. If used in the wrong way, you might
+	// expose your authentication information over unencrypted channels!
+	//
+	// https://msopenspecs.azureedge.net/files/MS-XLOGIN/%5bMS-XLOGIN%5d.pdf
+	//
+	// https://datatracker.ietf.org/doc/html/draft-murchison-sasl-login-00
+	SMTPAuthLoginNoEnc SMTPAuthType = "LOGIN-NOENC"
+
 	// SMTPAuthNoAuth is equivalent to performing no authentication at all. It is a convenience
 	// option and should not be used. Instead, for mail servers that do no support/require
 	// authentication, the Client should not be passed the WithSMTPAuth option at all.
-	SMTPAuthNoAuth SMTPAuthType = ""
+	SMTPAuthNoAuth SMTPAuthType = "NOAUTH"
 
 	// SMTPAuthPlain is the "PLAIN" authentication mechanism as described in RFC 4616.
 	//
-	// Since the "PLAIN" SASL authentication mechansim transmits the username and password in
+	// Since the "PLAIN" SASL authentication mechanism transmits the username and password in
 	// plaintext over the internet connection, we only allow this mechanism over a TLS secured
 	// connection.
 	//
 	// https://datatracker.ietf.org/doc/html/rfc4616/
 	SMTPAuthPlain SMTPAuthType = "PLAIN"
 
+	// SMTPAuthPlainNoEnc is the "PLAIN" authentication mechanism as described in RFC 4616.
+	//
+	// Since the "PLAIN" SASL authentication mechanism transmits the username and password in
+	// plaintext over the internet connection, by default we only allow this mechanism over
+	// a TLS secured connection. This authentiation mechanism overrides this default and will
+	// allow PLAIN authentication via an unencrypted channel. This can be useful if the
+	// connection has already been secured in a different way (e. g. a SSH tunnel)
+	//
+	// Note: Use this authentication method with caution. If used in the wrong way, you might
+	// expose your authentication information over unencrypted channels!
+	//
+	// https://datatracker.ietf.org/doc/html/rfc4616/
+	SMTPAuthPlainNoEnc SMTPAuthType = "PLAIN-NOENC"
+
 	// SMTPAuthXOAUTH2 is the "XOAUTH2" SASL authentication mechanism.
 	// https://developers.google.com/gmail/imap/xoauth2-protocol
 	SMTPAuthXOAUTH2 SMTPAuthType = "XOAUTH2"
@@ -76,7 +113,7 @@ const (
 	//
 	// SCRAM-SHA-X-PLUS authentication require TLS channel bindings to protect against MitM attacks and
 	// to guarantee that the integrity of the transport layer is preserved throughout the authentication
-	// process. Therefore we only allow this mechansim over a TLS secured connection.
+	// process. Therefore we only allow this mechanism over a TLS secured connection.
 	//
 	// SCRAM-SHA-1-PLUS is still considered secure for certain applications, particularly when used as part
 	// of a challenge-response authentication mechanism (as we use it). However, it is generally
@@ -95,7 +132,7 @@ const (
 	//
 	// SCRAM-SHA-X-PLUS authentication require TLS channel bindings to protect against MitM attacks and
 	// to guarantee that the integrity of the transport layer is preserved throughout the authentication
-	// process. Therefore we only allow this mechansim over a TLS secured connection.
+	// process. Therefore we only allow this mechanism over a TLS secured connection.
 	//
 	// https://datatracker.ietf.org/doc/html/rfc7677
 	SMTPAuthSCRAMSHA256PLUS SMTPAuthType = "SCRAM-SHA-256-PLUS"
@@ -134,3 +171,37 @@ var (
 	// authentication type.
 	ErrSCRAMSHA256PLUSAuthNotSupported = errors.New("server does not support SMTP AUTH type: SCRAM-SHA-256-PLUS")
 )
+
+// UnmarshalString satisfies the fig.StringUnmarshaler interface for the SMTPAuthType type
+// https://pkg.go.dev/github.com/kkyr/fig#StringUnmarshaler
+func (sa *SMTPAuthType) UnmarshalString(value string) error {
+	switch strings.ToLower(value) {
+	case "cram-md5", "crammd5", "cram":
+		*sa = SMTPAuthCramMD5
+	case "custom":
+		*sa = SMTPAuthCustom
+	case "login":
+		*sa = SMTPAuthLogin
+	case "login-noenc":
+		*sa = SMTPAuthLoginNoEnc
+	case "none", "noauth", "no":
+		*sa = SMTPAuthNoAuth
+	case "plain":
+		*sa = SMTPAuthPlain
+	case "plain-noenc":
+		*sa = SMTPAuthPlainNoEnc
+	case "scram-sha-1", "scram-sha1", "scramsha1":
+		*sa = SMTPAuthSCRAMSHA1
+	case "scram-sha-1-plus", "scram-sha1-plus", "scramsha1plus":
+		*sa = SMTPAuthSCRAMSHA1PLUS
+	case "scram-sha-256", "scram-sha256", "scramsha256":
+		*sa = SMTPAuthSCRAMSHA256
+	case "scram-sha-256-plus", "scram-sha256-plus", "scramsha256plus":
+		*sa = SMTPAuthSCRAMSHA256PLUS
+	case "xoauth2", "oauth2":
+		*sa = SMTPAuthXOAUTH2
+	default:
+		return fmt.Errorf("unsupported SMTP auth type: %s", value)
+	}
+	return nil
+}

auth_test.go

@@ -0,0 +1,59 @@
+// SPDX-FileCopyrightText: 2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT
+
+package mail
+
+import "testing"
+
+func TestSMTPAuthType_UnmarshalString(t *testing.T) {
+	tests := []struct {
+		name       string
+		authString string
+		expected   SMTPAuthType
+	}{
+		{"CRAM-MD5: cram-md5", "cram-md5", SMTPAuthCramMD5},
+		{"CRAM-MD5: crammd5", "crammd5", SMTPAuthCramMD5},
+		{"CRAM-MD5: cram", "cram", SMTPAuthCramMD5},
+		{"CUSTOM", "custom", SMTPAuthCustom},
+		{"LOGIN", "login", SMTPAuthLogin},
+		{"LOGIN-NOENC", "login-noenc", SMTPAuthLoginNoEnc},
+		{"NONE: none", "none", SMTPAuthNoAuth},
+		{"NONE: noauth", "noauth", SMTPAuthNoAuth},
+		{"NONE: no", "no", SMTPAuthNoAuth},
+		{"PLAIN", "plain", SMTPAuthPlain},
+		{"PLAIN-NOENC", "plain-noenc", SMTPAuthPlainNoEnc},
+		{"SCRAM-SHA-1: scram-sha-1", "scram-sha-1", SMTPAuthSCRAMSHA1},
+		{"SCRAM-SHA-1: scram-sha1", "scram-sha1", SMTPAuthSCRAMSHA1},
+		{"SCRAM-SHA-1: scramsha1", "scramsha1", SMTPAuthSCRAMSHA1},
+		{"SCRAM-SHA-1-PLUS: scram-sha-1-plus", "scram-sha-1-plus", SMTPAuthSCRAMSHA1PLUS},
+		{"SCRAM-SHA-1-PLUS: scram-sha1-plus", "scram-sha1-plus", SMTPAuthSCRAMSHA1PLUS},
+		{"SCRAM-SHA-1-PLUS: scramsha1plus", "scramsha1plus", SMTPAuthSCRAMSHA1PLUS},
+		{"SCRAM-SHA-256: scram-sha-256", "scram-sha-256", SMTPAuthSCRAMSHA256},
+		{"SCRAM-SHA-256: scram-sha256", "scram-sha256", SMTPAuthSCRAMSHA256},
+		{"SCRAM-SHA-256: scramsha256", "scramsha256", SMTPAuthSCRAMSHA256},
+		{"SCRAM-SHA-256-PLUS: scram-sha-256-plus", "scram-sha-256-plus", SMTPAuthSCRAMSHA256PLUS},
+		{"SCRAM-SHA-256-PLUS: scram-sha256-plus", "scram-sha256-plus", SMTPAuthSCRAMSHA256PLUS},
+		{"SCRAM-SHA-256-PLUS: scramsha256plus", "scramsha256plus", SMTPAuthSCRAMSHA256PLUS},
+		{"XOAUTH2: xoauth2", "xoauth2", SMTPAuthXOAUTH2},
+		{"XOAUTH2: oauth2", "oauth2", SMTPAuthXOAUTH2},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			var authType SMTPAuthType
+			if err := authType.UnmarshalString(tt.authString); err != nil {
+				t.Errorf("UnmarshalString() for type %s failed: %s", tt.authString, err)
+			}
+			if authType != tt.expected {
+				t.Errorf("UnmarshalString() for type %s failed: expected %s, got %s",
+					tt.authString, tt.expected, authType)
+			}
+		})
+	}
+	t.Run("should fail", func(t *testing.T) {
+		var authType SMTPAuthType
+		if err := authType.UnmarshalString("invalid"); err == nil {
+			t.Error("UnmarshalString() should have failed")
+		}
+	})
+}

b64linebreaker.go

@@ -13,8 +13,8 @@ import (
 // in encoding processes.
 var newlineBytes = []byte(SingleNewLine)
 
-// ErrNoOutWriter is the error message returned when no io.Writer is set for Base64LineBreaker.
-const ErrNoOutWriter = "no io.Writer set for Base64LineBreaker"
+// ErrNoOutWriter is the error returned when no io.Writer is set for Base64LineBreaker.
+var ErrNoOutWriter = errors.New("no io.Writer set for Base64LineBreaker")
 
 // Base64LineBreaker handles base64 encoding with the insertion of new lines after a certain number
 // of characters.
@@ -44,7 +44,7 @@ type Base64LineBreaker struct {
 //   - err: An error if one occurred during the write operation.
 func (l *Base64LineBreaker) Write(data []byte) (numBytes int, err error) {
 	if l.out == nil {
-		err = errors.New(ErrNoOutWriter)
+		err = ErrNoOutWriter
 		return
 	}
 	if l.used+len(data) < MaxBodyLength {

b64linebreaker_test.go

@@ -5,487 +5,165 @@
 package mail
 
 import (
-	"bufio"
 	"bytes"
 	"encoding/base64"
 	"errors"
-	"fmt"
 	"io"
 	"os"
 	"testing"
 )
 
-const logoB64 = `PD94bWwgdmVyc2lvbj0iMS4wIiBlbmNvZGluZz0iVVRGLTgiIHN0YW5kYWxvbmU9Im5vIj8+PCFE
-T0NUWVBFIHN2ZyBQVUJMSUMgIi0vL1czQy8vRFREIFNWRyAxLjEvL0VOIiAiaHR0cDovL3d3dy53
-My5vcmcvR3JhcGhpY3MvU1ZHLzEuMS9EVEQvc3ZnMTEuZHRkIj48c3ZnIHdpZHRoPSIxMDAlIiBo
-ZWlnaHQ9IjEwMCUiIHZpZXdCb3g9IjAgMCA2MDAgNjAwIiB2ZXJzaW9uPSIxLjEiIHhtbG5zPSJo
-dHRwOi8vd3d3LnczLm9yZy8yMDAwL3N2ZyIgeG1sbnM6eGxpbms9Imh0dHA6Ly93d3cudzMub3Jn
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-dHJva2UtbGluZWNhcDpyb3VuZDtzdHJva2UtbGluZWpvaW46cm91bmQ7c3Ryb2tlLW1pdGVybGlt
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-MDksMTMuMzMgLTE3LjE2NywyNi42NDYgLTIuNDM1LDMxLjUxOWMxNC43MzIsNC44NzMgNjIuNjU0
-LC0xOS4yMjggNjIuNjU0LC0xOS4yMjhaIiBzdHlsZT0iZmlsbDojNzM1ZDkzO3N0cm9rZTojMDAw
-O3N0cm9rZS13aWR0aDo1LjkzcHg7Ii8+PHBhdGggZD0iTTM3NC4xNDgsMTM2Ljg3NmMtMCwwIDM4
-LjQ5MywtOS4zMzggMzYuNTYzLC0zLjU0OWMtMS45Myw1Ljc5IC0zNy42MzgsMjYuOTAxIC0xMTQu
-ODMxLDE1Ljk2NmM3MC4zNDUsLTEwLjczMSA3OC4yNjgsLTEyLjQxNyA3OC4yNjgsLTEyLjQxN1oi
-IHN0eWxlPSJmaWxsOiM1MDNhNzE7c3Ryb2tlOiMwMDA7c3Ryb2tlLXdpZHRoOjQuOTVweDsiLz48
-cGF0aCBkPSJNMzU3LjM0NiwxMjQuOTA2bC01NC4wMjEsOS42MTJsLTAsNS4zOTlsNTQuMDIxLC05
-LjYxMmwwLC01LjM5OVoiIHN0eWxlPSJmaWxsOiNmZmY7Ii8+PGNpcmNsZSBjeD0iMzAwLjE1IiBj
-eT0iMTM3LjE5OCIgcj0iNC42NzciIHN0eWxlPSJmaWxsOiNmZmIyNWM7c3Ryb2tlOiMwMDA7c3Ry
-b2tlLXdpZHRoOjQuOTVweDsiLz48Y2lyY2xlIGN4PSIzNjEuNDEiIGN5PSIxMjcuNTgxIiByPSI0
-LjI4MiIgc3R5bGU9ImZpbGw6I2ZmYjI1YztzdHJva2U6IzAwMDtzdHJva2Utd2lkdGg6NC45NXB4
-OyIvPjwvZz48L3N2Zz4=
-`
-
 var (
-	errMockDefault = errors.New("mock write error")
-	errMockNewline = errors.New("mock newline error")
+	errClosedWriter = errors.New("writer is already closed")
+	errMockDefault  = errors.New("mock write error")
+	errMockNewline  = errors.New("mock newline error")
 )
 
-// TestBase64LineBreaker tests the Write and Close methods of the Base64LineBreaker
 func TestBase64LineBreaker(t *testing.T) {
-	l, err := os.Open("assets/gopher2.svg")
-	if err != nil {
-		t.Errorf("failed to open gopher logo asset: %s", err)
-		return
-	}
-	defer func() { _ = l.Close() }()
-
-	var wbuf bytes.Buffer
-	lb := Base64LineBreaker{out: &wbuf}
-	bw := base64.NewEncoder(base64.StdEncoding, &lb)
-	if _, err := io.Copy(bw, l); err != nil {
-		t.Errorf("failed to write logo asset to line breaker: %s", err)
-		return
-	}
-	if err := bw.Close(); err != nil {
-		t.Errorf("failed to close b64 encoder: %s", err)
-	}
-	if err := lb.Close(); err != nil {
-		t.Errorf("failed to close line breaker: %s", err)
-	}
-	ob := removeNewLines([]byte(logoB64))
-	nb := removeNewLines(wbuf.Bytes())
-	if string(ob) != string(nb) {
-		t.Errorf("generated line breaker output differs from original data")
-	}
-}
-
-// TestBase64LineBreakerFailures tests the cases in which the Base64LineBreaker would fail
-func TestBase64LineBreakerFailures(t *testing.T) {
-	stt := []byte("short")
-	ltt := []byte(logoB64)
-
-	// No output writer defined
-	lb := Base64LineBreaker{}
-	if _, err := lb.Write(stt); err == nil {
-		t.Errorf("writing to Base64LineBreaker with no output io.Writer was supposed to failed, but didn't")
-	}
-	if err := lb.Close(); err != nil {
-		t.Errorf("failed to close Base64LineBreaker: %s", err)
-	}
-
-	// Closed output writer
-	wbuf := errorWriter{}
-	fb := Base64LineBreaker{out: wbuf}
-	if _, err := fb.Write(ltt); err == nil {
-		t.Errorf("writing to Base64LineBreaker with errorWriter was supposed to failed, but didn't")
-	}
-	if err := fb.Close(); err != nil {
-		t.Errorf("failed to close Base64LineBreaker: %s", err)
-	}
-}
-
-func TestBase64LineBreaker_WriteAndClose(t *testing.T) {
-	tests := []struct {
-		name   string
-		data   []byte
-		writer io.Writer
-	}{
-		{
-			name:   "Write data within MaxBodyLength",
-			data:   []byte("testdata"),
-			writer: &mockWriterExcess{writeError: errMockDefault},
-		},
-		{
-			name: "Write data exceeds MaxBodyLength",
-			data: []byte("verylongtestdataverylongtestdataverylongtestdata" +
-				"verylongtestdataverylongtestdataverylongtestdata"),
-			writer: &mockWriterExcess{writeError: errMockDefault},
-		},
-		{
-			name: "Write data exceeds MaxBodyLength with newline",
-			data: []byte("verylongtestdataverylongtestdataverylongtestdata" +
-				"verylongtestdataverylongtestdataverylongtestdata"),
-			writer: &mockWriterNewline{writeError: errMockDefault},
-		},
-	}
-
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			blr := &Base64LineBreaker{out: tt.writer}
-
-			_, err := blr.Write(tt.data)
-			if err != nil && !errors.Is(err, errMockDefault) && !errors.Is(err, errMockNewline) {
-				t.Errorf("Unexpected error while writing: %v", err)
-			}
-			err = blr.Close()
-			if err != nil && !errors.Is(err, errMockDefault) && !errors.Is(err, errMockNewline) {
-				t.Errorf("Unexpected error while closing: %v", err)
+	t.Run("write, copy and close", func(t *testing.T) {
+		logoWriter := bytes.NewBuffer(nil)
+		lineBreaker := &Base64LineBreaker{out: logoWriter}
+		t.Cleanup(func() {
+			if err := lineBreaker.Close(); err != nil {
+				t.Errorf("failed to close line breaker: %s", err)
 			}
 		})
-	}
+		if _, err := lineBreaker.Write([]byte("testdata")); err != nil {
+			t.Errorf("failed to write to line breaker: %s", err)
+		}
+	})
+	t.Run("write actual data and compare with expected results", func(t *testing.T) {
+		logo, err := os.Open("testdata/logo.svg")
+		if err != nil {
+			t.Fatalf("failed to open test data file: %s", err)
+		}
+		t.Cleanup(func() {
+			if err := logo.Close(); err != nil {
+				t.Errorf("failed to close test data file: %s", err)
+			}
+		})
+
+		logoWriter := bytes.NewBuffer(nil)
+		lineBreaker := &Base64LineBreaker{out: logoWriter}
+		t.Cleanup(func() {
+			if err := lineBreaker.Close(); err != nil {
+				t.Errorf("failed to close line breaker: %s", err)
+			}
+		})
+		base64Encoder := base64.NewEncoder(base64.StdEncoding, lineBreaker)
+		t.Cleanup(func() {
+			if err := base64Encoder.Close(); err != nil {
+				t.Errorf("failed to close base64 encoder: %s", err)
+			}
+		})
+		copiedBytes, err := io.Copy(base64Encoder, logo)
+		if err != nil {
+			t.Errorf("failed to copy test data to line breaker: %s", err)
+		}
+		if err = base64Encoder.Close(); err != nil {
+			t.Errorf("failed to close base64 encoder: %s", err)
+		}
+		if err = lineBreaker.Close(); err != nil {
+			t.Errorf("failed to close line breaker: %s", err)
+		}
+
+		logoStat, err := os.Stat("testdata/logo.svg")
+		if err != nil {
+			t.Fatalf("failed to stat test data file: %s", err)
+		}
+		if logoStat.Size() != copiedBytes {
+			t.Errorf("copied %d bytes, but expected %d bytes", copiedBytes, logoStat.Size())
+		}
+
+		expectedRaw, err := os.ReadFile("testdata/logo.svg.base64")
+		if err != nil {
+			t.Errorf("failed to read expected base64 data from file: %s", err)
+		}
+		expected := removeNewLines(t, expectedRaw)
+		got := removeNewLines(t, logoWriter.Bytes())
+		if !bytes.EqualFold(expected, got) {
+			t.Errorf("generated line breaker output differs from expected data")
+		}
+	})
+	t.Run("fail with no writer defined", func(t *testing.T) {
+		lineBreaker := &Base64LineBreaker{}
+		_, err := lineBreaker.Write([]byte("testdata"))
+		if err == nil {
+			t.Errorf("writing to Base64LineBreaker with no output io.Writer was supposed to failed, but didn't")
+		}
+		if !errors.Is(err, ErrNoOutWriter) {
+			t.Errorf("unexpected error while writing to empty Base64LineBreaker: %s", err)
+		}
+		if err := lineBreaker.Close(); err != nil {
+			t.Errorf("failed to close Base64LineBreaker: %s", err)
+		}
+	})
+	t.Run("write on an already closed output writer", func(t *testing.T) {
+		logo, err := os.Open("testdata/logo.svg")
+		if err != nil {
+			t.Fatalf("failed to open test data file: %s", err)
+		}
+		t.Cleanup(func() {
+			if err := logo.Close(); err != nil {
+				t.Errorf("failed to close test data file: %s", err)
+			}
+		})
+
+		writeBuffer := &errorWriter{}
+		lineBreaker := &Base64LineBreaker{out: writeBuffer}
+		_, err = io.Copy(lineBreaker, logo)
+		if err == nil {
+			t.Errorf("writing to Base64LineBreaker with an already closed output io.Writer was " +
+				"supposed to failed, but didn't")
+		}
+		if !errors.Is(err, errClosedWriter) {
+			t.Errorf("unexpected error while writing to Base64LineBreaker: %s", err)
+		}
+	})
+	t.Run("fail on different scenarios with mock writer", func(t *testing.T) {
+		tests := []struct {
+			name   string
+			data   []byte
+			writer io.Writer
+		}{
+			{
+				name:   "write data within MaxBodyLength",
+				data:   []byte("testdata"),
+				writer: &mockWriterExcess{writeError: errMockDefault},
+			},
+			{
+				name: "write data exceeds MaxBodyLength",
+				data: []byte("verylongtestdataverylongtestdataverylongtestdata" +
+					"verylongtestdataverylongtestdataverylongtestdata"),
+				writer: &mockWriterExcess{writeError: errMockDefault},
+			},
+			{
+				name: "write data exceeds MaxBodyLength with newline",
+				data: []byte("verylongtestdataverylongtestdataverylongtestdata" +
+					"verylongtestdataverylongtestdataverylongtestdata"),
+				writer: &mockWriterNewline{writeError: errMockDefault},
+			},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				lineBreaker := &Base64LineBreaker{out: tt.writer}
+
+				_, err := lineBreaker.Write(tt.data)
+				if err != nil && !errors.Is(err, errMockDefault) && !errors.Is(err, errMockNewline) {
+					t.Errorf("unexpected error while writing to mock writer: %s", err)
+				}
+				err = lineBreaker.Close()
+				if err != nil && !errors.Is(err, errMockDefault) && !errors.Is(err, errMockNewline) {
+					t.Errorf("unexpected error while closing mock writer: %s", err)
+				}
+			})
+		}
+	})
 }
 
-// removeNewLines removes any newline characters from the given data
-func removeNewLines(data []byte) []byte {
+// removeNewLines is a test helper thatremoves all newline characters ('\r' and '\n') from the given byte slice.
+func removeNewLines(t *testing.T, data []byte) []byte {
+	t.Helper()
 	result := make([]byte, len(data))
 	n := 0
 
@@ -503,11 +181,11 @@ func removeNewLines(data []byte) []byte {
 type errorWriter struct{}
 
 func (e errorWriter) Write([]byte) (int, error) {
-	return 0, fmt.Errorf("supposed to always fail")
+	return 0, errClosedWriter
 }
 
 func (e errorWriter) Close() error {
-	return fmt.Errorf("supposed to always fail")
+	return errClosedWriter
 }
 
 type mockWriterExcess struct {
@@ -539,19 +217,49 @@ func (w *mockWriterNewline) Write(p []byte) (n int, err error) {
 	}
 }
 
-func FuzzBase64LineBreaker_Write(f *testing.F) {
-	f.Add([]byte("abc"))
-	f.Add([]byte("def"))
-	f.Add([]uint8{0o0, 0o1, 0o2, 30, 255})
-	buf := bytes.Buffer{}
-	bw := bufio.NewWriter(&buf)
+func FuzzBase64LineBreaker(f *testing.F) {
+	seedData := [][]byte{
+		[]byte(""),
+		[]byte("abc"),
+		[]byte("def"),
+		[]byte("Hello, World!"),
+		[]byte("abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789!§$%&/()=?`{[]}\\|^~*+#-._'"),
+		[]byte("ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789+/"),
+		bytes.Repeat([]byte("A"), MaxBodyLength-1),  // Near the line length limit
+		bytes.Repeat([]byte("A"), MaxBodyLength),    // Exactly the line length limit
+		bytes.Repeat([]byte("A"), MaxBodyLength+1),  // Slightly above the line length limit
+		bytes.Repeat([]byte("A"), MaxBodyLength*3),  // Tripple exceed the line length limit
+		bytes.Repeat([]byte("A"), MaxBodyLength*10), // Tenfold exceed the line length limit
+		{0o0, 0o1, 0o2, 30, 255},
+	}
+	for _, data := range seedData {
+		f.Add(data)
+	}
+
 	f.Fuzz(func(t *testing.T, data []byte) {
-		b := &Base64LineBreaker{out: bw}
-		if _, err := b.Write(data); err != nil {
-			t.Errorf("failed to write to B64LineBreaker: %s", err)
+		buffer := bytes.NewBuffer(nil)
+		lineBreaker := &Base64LineBreaker{
+			out: buffer,
 		}
-		if err := b.Close(); err != nil {
-			t.Errorf("failed to close B64LineBreaker: %s", err)
+		base64Encoder := base64.NewEncoder(base64.StdEncoding, lineBreaker)
+
+		_, err := base64Encoder.Write(data)
+		if err != nil {
+			t.Errorf("failed to write test data to base64 encoder: %s", err)
+		}
+		if err = base64Encoder.Close(); err != nil {
+			t.Errorf("failed to close base64 encoder: %s", err)
+		}
+		if err = lineBreaker.Close(); err != nil {
+			t.Errorf("failed to close base64 line breaker: %s", err)
+		}
+
+		decode, err := base64.StdEncoding.DecodeString(buffer.String())
+		if err != nil {
+			t.Errorf("failed to decode base64 data: %s", err)
+		}
+		if !bytes.Equal(data, decode) {
+			t.Error("generated line breaker output differs from original data")
 		}
 	})
 }

client.go

@@ -145,6 +145,9 @@ type (
 		// isEncrypted indicates wether the Client connection is encrypted or not.
 		isEncrypted bool
 
+		// logAuthData indicates whether authentication-related data should be logged.
+		logAuthData bool
+
 		// logger is a logger that satisfies the log.Logger interface.
 		logger log.Logger
 
@@ -239,6 +242,12 @@ var (
 	// provided as argument to the WithDSN Option.
 	ErrInvalidDSNRcptNotifyCombination = errors.New("DSN rcpt notify option NEVER cannot be " +
 		"combined with any of SUCCESS, FAILURE or DELAY")
+
+	// ErrSMTPAuthMethodIsNil indicates that the SMTP authentication method provided is nil
+	ErrSMTPAuthMethodIsNil = errors.New("SMTP auth method is nil")
+
+	// ErrDialContextFuncIsNil indicates that a required dial context function is not provided.
+	ErrDialContextFuncIsNil = errors.New("dial context function is nil")
 )
 
 // NewClient creates a new Client instance with the provided host and optional configuration Option functions.
@@ -256,11 +265,12 @@ var (
 //   - An error if any critical default values are missing or options fail to apply.
 func NewClient(host string, opts ...Option) (*Client, error) {
 	c := &Client{
-		connTimeout: DefaultTimeout,
-		host:        host,
-		port:        DefaultPort,
-		tlsconfig:   &tls.Config{ServerName: host, MinVersion: DefaultTLSMinVersion},
-		tlspolicy:   DefaultTLSPolicy,
+		smtpAuthType: SMTPAuthNoAuth,
+		connTimeout:  DefaultTimeout,
+		host:         host,
+		port:         DefaultPort,
+		tlsconfig:    &tls.Config{ServerName: host, MinVersion: DefaultTLSMinVersion},
+		tlspolicy:    DefaultTLSPolicy,
 	}
 
 	// Set default HELO/EHLO hostname
@@ -364,9 +374,10 @@ func WithSSLPort(fallback bool) Option {
 // WithDebugLog enables debug logging for the Client.
 //
 // This function activates debug logging, which logs incoming and outgoing communication between the
-// Client and the SMTP server to os.Stderr. Be cautious when using this option, as the logs may include
-// unencrypted authentication data, depending on the SMTP authentication method in use, which could
-// pose a data protection risk.
+// Client and the SMTP server to os.Stderr. By default the debug logging will redact any kind of SMTP
+// authentication data. If you need access to the actual authentication data in your logs, you can
+// enable authentication data logging with the WithLogAuthData option or by setting it with the
+// Client.SetLogAuthData method.
 //
 // Returns:
 //   - An Option function that enables debug logging for the Client.
@@ -505,6 +516,9 @@ func WithSMTPAuth(authtype SMTPAuthType) Option {
 //   - An Option function that sets the custom SMTP authentication for the Client.
 func WithSMTPAuthCustom(smtpAuth smtp.Auth) Option {
 	return func(c *Client) error {
+		if smtpAuth == nil {
+			return ErrSMTPAuthMethodIsNil
+		}
 		c.smtpAuth = smtpAuth
 		c.smtpAuthType = SMTPAuthCustom
 		return nil
@@ -666,11 +680,30 @@ func WithoutNoop() Option {
 //   - An Option function that sets the custom DialContextFunc for the Client.
 func WithDialContextFunc(dialCtxFunc DialContextFunc) Option {
 	return func(c *Client) error {
+		if dialCtxFunc == nil {
+			return ErrDialContextFuncIsNil
+		}
 		c.dialContextFunc = dialCtxFunc
 		return nil
 	}
 }
 
+// WithLogAuthData enables logging of authentication data.
+//
+// This function sets the logAuthData field of the Client to true, enabling the logging of authentication data.
+//
+// Be cautious when using this option, as the logs may include unencrypted authentication data, depending on
+// the SMTP authentication method in use, which could pose a data protection risk.
+//
+// Returns:
+//   - An Option function that configures the Client to enable authentication data logging.
+func WithLogAuthData() Option {
+	return func(c *Client) error {
+		c.logAuthData = true
+		return nil
+	}
+}
+
 // TLSPolicy returns the TLSPolicy that is currently set on the Client as a string.
 //
 // This method retrieves the current TLSPolicy configured for the Client and returns it as a string representation.
@@ -718,6 +751,7 @@ func (c *Client) SetTLSPolicy(policy TLSPolicy) {
 func (c *Client) SetTLSPortPolicy(policy TLSPolicy) {
 	if c.port == DefaultPort {
 		c.port = DefaultPortTLS
+		c.fallbackPort = 0
 
 		if policy == TLSOpportunistic {
 			c.fallbackPort = DefaultPort
@@ -865,6 +899,19 @@ func (c *Client) SetSMTPAuthCustom(smtpAuth smtp.Auth) {
 	c.smtpAuthType = SMTPAuthCustom
 }
 
+// SetLogAuthData sets or overrides the logging of SMTP authentication data for the Client.
+//
+// This function sets the logAuthData field of the Client to true, enabling the logging of authentication data.
+//
+// Be cautious when using this option, as the logs may include unencrypted authentication data, depending on
+// the SMTP authentication method in use, which could pose a data protection risk.
+//
+// Parameters:
+//   - logAuth: Set wether or not to log SMTP authentication data for the Client.
+func (c *Client) SetLogAuthData(logAuth bool) {
+	c.logAuthData = logAuth
+}
+
 // DialWithContext establishes a connection to the server using the provided context.Context.
 //
 // This function adds a deadline based on the Client's timeout to the provided context.Context
@@ -921,6 +968,9 @@ func (c *Client) DialWithContext(dialCtx context.Context) error {
 	if c.useDebugLog {
 		c.smtpClient.SetDebugLog(true)
 	}
+	if c.logAuthData {
+		c.smtpClient.SetLogAuthData()
+	}
 	if err = c.smtpClient.Hello(c.helo); err != nil {
 		return err
 	}
@@ -1028,19 +1078,23 @@ func (c *Client) DialAndSendWithContext(ctx context.Context, messages ...*Msg) e
 // determines the supported authentication methods, and applies the appropriate authentication
 // type. An error is returned if authentication fails.
 //
-// This method first verifies the connection to the SMTP server. If no custom authentication
-// mechanism is provided, it checks which authentication methods are supported by the server.
-// Based on the configured SMTPAuthType, it sets up the appropriate authentication mechanism.
+// By default NewClient sets the SMTP authentication type to SMTPAuthNoAuth, meaning, that no
+// SMTP authentication will be performed. If the user makes use of SetSMTPAuth or initialzes the
+// client with WithSMTPAuth, the SMTP authentication type will be set in the Client, forcing
+// this method to determine if the server supports the selected authentication method and
+// assigning the corresponding smtp.Auth function to it.
+//
+// If the user set a custom SMTP authentication function using SetSMTPAuthCustom or
+// WithSMTPAuthCustom, we will not perform any detection and assignment logic and will trust
+// the user with their provided smtp.Auth function.
+//
 // Finally, it attempts to authenticate the client using the selected method.
 //
 // Returns:
 //   - An error if the connection check fails, if no supported authentication method is found,
 //     or if the authentication process fails.
 func (c *Client) auth() error {
-	if err := c.checkConn(); err != nil {
-		return fmt.Errorf("failed to authenticate: %w", err)
-	}
-	if c.smtpAuth == nil && c.smtpAuthType != SMTPAuthCustom {
+	if c.smtpAuth == nil && c.smtpAuthType != SMTPAuthNoAuth {
 		hasSMTPAuth, smtpAuthType := c.smtpClient.Extension("AUTH")
 		if !hasSMTPAuth {
 			return fmt.Errorf("server does not support SMTP AUTH")
@@ -1051,12 +1105,22 @@ func (c *Client) auth() error {
 			if !strings.Contains(smtpAuthType, string(SMTPAuthPlain)) {
 				return ErrPlainAuthNotSupported
 			}
-			c.smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host)
+			c.smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host, false)
+		case SMTPAuthPlainNoEnc:
+			if !strings.Contains(smtpAuthType, string(SMTPAuthPlain)) {
+				return ErrPlainAuthNotSupported
+			}
+			c.smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host, true)
 		case SMTPAuthLogin:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthLogin)) {
 				return ErrLoginAuthNotSupported
 			}
-			c.smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host)
+			c.smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host, false)
+		case SMTPAuthLoginNoEnc:
+			if !strings.Contains(smtpAuthType, string(SMTPAuthLogin)) {
+				return ErrLoginAuthNotSupported
+			}
+			c.smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host, true)
 		case SMTPAuthCramMD5:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthCramMD5)) {
 				return ErrCramMD5AuthNotSupported
@@ -1197,14 +1261,13 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 			affectedMsg: message,
 		}
 	}
-	message.isDelivered = true
-
 	if err = writer.Close(); err != nil {
 		return &SendError{
 			Reason: ErrSMTPDataClose, errlist: []error{err}, isTemp: isTempError(err),
 			affectedMsg: message,
 		}
 	}
+	message.isDelivered = true
 
 	if err = c.Reset(); err != nil {
 		return &SendError{
@@ -1212,12 +1275,6 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 			affectedMsg: message,
 		}
 	}
-	if err = c.checkConn(); err != nil {
-		return &SendError{
-			Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err),
-			affectedMsg: message,
-		}
-	}
 	return nil
 }
 
@@ -1234,6 +1291,9 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 //   - An error if there is no active connection, if the NOOP command fails, or if extending
 //     the deadline fails; otherwise, returns nil.
 func (c *Client) checkConn() error {
+	if c.smtpClient == nil {
+		return ErrNoActiveConnection
+	}
 	if !c.smtpClient.HasConnection() {
 		return ErrNoActiveConnection
 	}
@@ -1292,9 +1352,6 @@ func (c *Client) setDefaultHelo() error {
 //   - An error if there is no active connection, if STARTTLS is required but not supported,
 //     or if there are issues during the TLS handshake; otherwise, returns nil.
 func (c *Client) tls() error {
-	if !c.smtpClient.HasConnection() {
-		return ErrNoActiveConnection
-	}
 	if !c.useSSL && c.tlspolicy != NoTLS {
 		hasStartTLS := false
 		extension, _ := c.smtpClient.Extension("STARTTLS")

client_121_test.go

@@ -0,0 +1,126 @@
+// SPDX-FileCopyrightText: 2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT
+
+//go:build go1.21
+// +build go1.21
+
+package mail
+
+import (
+	"bytes"
+	"context"
+	"errors"
+	"fmt"
+	"net"
+	"os"
+	"reflect"
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/wneessen/go-mail/log"
+)
+
+func TestNewClientNewVersionsOnly(t *testing.T) {
+	tests := []struct {
+		name       string
+		option     Option
+		expectFunc func(c *Client) error
+		shouldfail bool
+		expectErr  *error
+	}{
+		{
+			"WithLogger log.JSONlog", WithLogger(log.NewJSON(os.Stderr, log.LevelDebug)),
+			func(c *Client) error {
+				if c.logger == nil {
+					return errors.New("failed to set logger. Want logger bug got got nil")
+				}
+				loggerType := reflect.TypeOf(c.logger).String()
+				if loggerType != "*log.JSONlog" {
+					return fmt.Errorf("failed to set logger. Want logger type: %s, got: %s",
+						"*log.JSONlog", loggerType)
+				}
+				return nil
+			},
+			false, nil,
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			client, err := NewClient(DefaultHost, tt.option)
+			if !tt.shouldfail && err != nil {
+				t.Fatalf("failed to create new client: %s", err)
+			}
+			if tt.shouldfail && err == nil {
+				t.Errorf("client creation was supposed to fail, but it didn't")
+			}
+			if tt.shouldfail && tt.expectErr != nil {
+				if !errors.Is(err, *tt.expectErr) {
+					t.Errorf("error for NewClient mismatch. Expected: %s, got: %s",
+						*tt.expectErr, err)
+				}
+			}
+			if tt.expectFunc != nil {
+				if err = tt.expectFunc(client); err != nil {
+					t.Errorf("NewClient with custom option failed: %s", err)
+				}
+			}
+		})
+	}
+}
+
+func TestClient_DialWithContextNewVersionsOnly(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+	PortAdder.Add(1)
+	serverPort := int(TestServerPortBase + PortAdder.Load())
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, t, &serverProps{FeatureSet: featureSet, ListenPort: serverPort}); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 30)
+	t.Run("connect with full debug logging and auth logging", func(t *testing.T) {
+		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		logBuffer := bytes.NewBuffer(nil)
+		client, err := NewClient(DefaultHost, WithPort(serverPort), WithTLSPolicy(NoTLS),
+			WithDebugLog(), WithLogAuthData(), WithLogger(log.NewJSON(logBuffer, log.LevelDebug)),
+			WithSMTPAuth(SMTPAuthPlain), WithUsername("test"), WithPassword("password"))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+
+		if err = client.DialWithContext(ctxDial); err != nil {
+			var netErr net.Error
+			if errors.As(err, &netErr) && netErr.Timeout() {
+				t.Skip("failed to connect to the test server due to timeout")
+			}
+			t.Fatalf("failed to connect to the test server: %s", err)
+		}
+		t.Cleanup(func() {
+			if err = client.Close(); err != nil {
+				t.Errorf("failed to close the client: %s", err)
+			}
+		})
+
+		logs := parseJSONLog(t, logBuffer)
+		if len(logs.Lines) == 0 {
+			t.Errorf("failed to enable debug logging, but no logs were found")
+		}
+		authFound := false
+		for _, logline := range logs.Lines {
+			if strings.EqualFold(logline.Message, "AUTH PLAIN AHRlc3QAcGFzc3dvcmQ=") &&
+				logline.Direction.From == "client" && logline.Direction.To == "server" {
+				authFound = true
+			}
+		}
+		if !authFound {
+			t.Errorf("logAuthData not working, no authentication info found in logs")
+		}
+	})
+}

codecov.yml

@@ -6,17 +6,17 @@ coverage:
   status:
     project:
       default:
-        target: 85%
-        threshold: 5%
+        target: 90%
+        threshold: 2%
         base: auto 
         if_ci_failed: error
         only_pulls: false
     patch:
       default:
-        target: 80%
+        target: 90%
         base: auto
         if_ci_failed: error
-        threshold: 5%
+        threshold: 2%
 
 comment:
   require_changes: true

doc.go

@@ -11,4 +11,4 @@ package mail
 
 // VERSION indicates the current version of the package. It is also attached to the default user
 // agent string.
-const VERSION = "0.5.0"
+const VERSION = "0.5.1"

eml.go

@@ -60,7 +60,7 @@ func EMLToMsgFromReader(reader io.Reader) (*Msg, error) {
 		return msg, fmt.Errorf("failed to parse EML from reader: %w", err)
 	}
 
-	if err := parseEML(parsedMsg, bodybuf, msg); err != nil {
+	if err = parseEML(parsedMsg, bodybuf, msg); err != nil {
 		return msg, fmt.Errorf("failed to parse EML contents: %w", err)
 	}
 
@@ -93,7 +93,7 @@ func EMLToMsgFromFile(filePath string) (*Msg, error) {
 		return msg, fmt.Errorf("failed to parse EML file: %w", err)
 	}
 
-	if err := parseEML(parsedMsg, bodybuf, msg); err != nil {
+	if err = parseEML(parsedMsg, bodybuf, msg); err != nil {
 		return msg, fmt.Errorf("failed to parse EML contents: %w", err)
 	}
 
@@ -218,9 +218,9 @@ func parseEMLHeaders(mailHeader *netmail.Header, msg *Msg) error {
 			for _, addr := range parsedAddrs {
 				addrStrings = append(addrStrings, addr.String())
 			}
-			if err = addrFunc(addrStrings...); err != nil {
-				return fmt.Errorf(`failed to parse %q header: %w`, addrHeader, err)
-			}
+			// We can skip the error checking here since netmail.ParseAddressList already performed the
+			// same address checking that the msg methods do.
+			_ = addrFunc(addrStrings...)
 		}
 	}
 
@@ -383,7 +383,7 @@ ReadNextPart:
 		return fmt.Errorf("failed to get next part of multipart message: %w", err)
 	}
 	for err == nil {
-		// Multipart/related and Multipart/alternative parts need to be parsed seperately
+		// Multipart/related and Multipart/alternative parts need to be parsed separately
 		if contentTypeSlice, ok := multiPart.Header[HeaderContentType.String()]; ok && len(contentTypeSlice) == 1 {
 			contentType, _ := parseMultiPartHeader(contentTypeSlice[0])
 			if strings.EqualFold(contentType, TypeMultipartRelated.String()) ||
@@ -600,6 +600,8 @@ func parseEMLAttachmentEmbed(contentDisposition []string, multiPart *multipart.P
 		if err := msg.EmbedReader(filename, dataReader); err != nil {
 			return fmt.Errorf("failed to embed multipart body: %w", err)
 		}
+	default:
+		return errors.New("unsupported content disposition type")
 	}
 	return nil
 }

eml_test.go

@@ -6,11 +6,8 @@ package mail
 
 import (
 	"bytes"
-	"fmt"
-	"os"
 	"strings"
 	"testing"
-	"time"
 )
 
 const (
@@ -22,6 +19,23 @@ Subject: Saying Hello
 Date: Fri, 21 Nov 1997 09:55:06 -0600
 Message-ID: <1234@local.machine.example>
 
+This is a message just to say hello.
+So, "Hello".`
+	exampleMailRFC5322A11InvalidFrom = `From: §§§§§§§§§
+To: Mary Smith <mary@example.net>
+Subject: Saying Hello
+Date: Fri, 21 Nov 1997 09:55:06 -0600
+Message-ID: <1234@local.machine.example>
+
+This is a message just to say hello.
+So, "Hello".`
+	exampleMailInvalidHeader = `From: John Doe <jdoe@machine.example>
+To: Mary Smith <mary@example.net>
+Inva@id*Header; This is a header
+Subject: Saying Hello
+Date: Fri, 21 Nov 1997 09:55:06 -0600
+Message-ID: <1234@local.machine.example>
+
 This is a message just to say hello.
 So, "Hello".`
 	exampleMailPlainNoEnc = `Date: Wed, 01 Nov 2023 00:00:00 +0000
@@ -42,6 +56,52 @@ This is a test mail. Please do not reply to this. Also this line is very long so
 should be wrapped.
 
 
+Thank your for your business!
+The go-mail team
+
+--
+This is a signature`
+	exampleMailPlainInvalidCTE = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // plain text without encoding
+User-Agent: go-mail v0.4.0 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.0 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: text/plain; charset=UTF-8
+Content-Transfer-Encoding: invalid
+
+Dear Customer,
+
+This is a test mail. Please do not reply to this. Also this line is very long so it
+should be wrapped.
+
+
+Thank your for your business!
+The go-mail team
+
+--
+This is a signature`
+	exampleMailInvalidContentType = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // plain text without encoding
+User-Agent: go-mail v0.4.0 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.0 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: text/plain @ charset=UTF-8; $foo; bar; --invalid--
+Content-Transfer-Encoding: 8bit
+
+Dear Customer,
+
+This is a test mail. Please do not reply to this. Also this line is very long so it
+should be wrapped.
+
+
 Thank your for your business!
 The go-mail team
 
@@ -304,6 +364,128 @@ VGhpcyBpcyBhIHNpbXBsZSB0ZXN0IHRleHQgZmlsZSBhdHRhY2htZW50LgoKSXQgCiAgaGFzCiAg
 ICAgc2V2ZXJhbAogICAgICAgICAgICBuZXdsaW5lcwoJICAgICAgICAgICAgYW5kCgkgICAgc3Bh
 Y2VzCiAgICAgaW4KICBpdAouCgpBcyB3ZWxsIGFzIGFuIGVtb2ppOiDwn5mCCg==
 
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7--`
+	exampleMailPlainB64WithAttachmentNoContentType = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // plain text base64 with attachment
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: multipart/mixed;
+ boundary=45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Transfer-Encoding: base64
+
+RGVhciBDdXN0b21lciwKClRoaXMgaXMgYSB0ZXN0IG1haWwuIFBsZWFzZSBkbyBub3QgcmVwbHkg
+dG8gdGhpcy4gQWxzbyB0aGlzIGxpbmUgaXMgdmVyeSBsb25nIHNvIGl0CnNob3VsZCBiZSB3cmFw
+cGVkLgoKClRoYW5rIHlvdXIgZm9yIHlvdXIgYnVzaW5lc3MhClRoZSBnby1tYWlsIHRlYW0KCi0t
+ClRoaXMgaXMgYSBzaWduYXR1cmU=
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Disposition: attachment; filename="test.attachment"
+Content-Transfer-Encoding: base64
+
+VGhpcyBpcyBhIHNpbXBsZSB0ZXN0IHRleHQgZmlsZSBhdHRhY2htZW50LgoKSXQgCiAgaGFzCiAg
+ICAgc2V2ZXJhbAogICAgICAgICAgICBuZXdsaW5lcwoJICAgICAgICAgICAgYW5kCgkgICAgc3Bh
+Y2VzCiAgICAgaW4KICBpdAouCgpBcyB3ZWxsIGFzIGFuIGVtb2ppOiDwn5mCCg==
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7--`
+	exampleMailPlainB64WithAttachmentBrokenB64 = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // plain text base64 with attachment
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: multipart/mixed;
+ boundary=45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Transfer-Encoding: base64
+Content-Type: text/plain; charset=UTF-8
+
+RGVhciBDdXN0b21lciwKClRoaXMgaXMgYSB0ZXN0IG1haWwuIFBsZWFzZSBkbyBub3QgcmVwbHkg
+dG8gdGhpcy4gQWxzbyB0aGl§§§§§@@@@@XMgdmVyeSBsb25nIHNvIGl0CnNob3VsZCBiZSB3cmFw
+cGVkLgoKClRoYW5rIHlvdXIgZm9yIHlvdXIgYnVzaW5lc3MhClRoZSBnby1tYWlsIHRlYW0KCi0t
+ClRoaXMgaXMgYSBzaWduYXR1cmU=
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Disposition: attachment; filename="test.attachment"
+Content-Transfer-Encoding: base64
+Content-Type: application/octet-stream; name="test.attachment"
+
+VGhpcyBpcyBhIHNpbXBsZSB0ZXN0IHRleHQgZmlsZSBhdHRhY2htZW50LgoKSXQgCiAgaGFzCiAg
+ICAgc2V2ZXJhbAogICAg§§§§§@@@@@BuZXdsaW5lcwoJICAgICAgICAgICAgYW5kCgkgICAgc3Bh
+Y2VzCiAgICAgaW4KICBpdAouCgpBcyB3ZWxsIGFzIGFuIGVtb2ppOiDwn5mCCg==
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7--`
+	exampleMailPlainB64WithAttachmentInvalidCTE = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // plain text base64 with attachment
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: multipart/mixed;
+ boundary=45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Transfer-Encoding: invalid
+Content-Type: text/plain; charset=UTF-8
+
+RGVhciBDdXN0b21lciwKClRoaXMgaXMgYSB0ZXN0IG1haWwuIFBsZWFzZSBkbyBub3QgcmVwbHkg
+dG8gdGhpcy4gQWxzbyB0aGlzIGxpbmUgaXMgdmVyeSBsb25nIHNvIGl0CnNob3VsZCBiZSB3cmFw
+cGVkLgoKClRoYW5rIHlvdXIgZm9yIHlvdXIgYnVzaW5lc3MhClRoZSBnby1tYWlsIHRlYW0KCi0t
+ClRoaXMgaXMgYSBzaWduYXR1cmU=
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Disposition: attachment; filename="test.attachment"
+Content-Transfer-Encoding: invalid
+Content-Type: application/octet-stream; name="test.attachment"
+
+VGhpcyBpcyBhIHNpbXBsZSB0ZXN0IHRleHQgZmlsZSBhdHRhY2htZW50LgoKSXQgCiAgaGFzCiAg
+ICAgc2V2ZXJhbAogICAgICAgICAgICBuZXdsaW5lcwoJICAgICAgICAgICAgYW5kCgkgICAgc3Bh
+Y2VzCiAgICAgaW4KICBpdAouCgpBcyB3ZWxsIGFzIGFuIGVtb2ppOiDwn5mCCg==
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7--`
+	exampleMailPlainB64WithAttachmentInvalidContentType = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // plain text base64 with attachment
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: multipart/mixed;
+ boundary=45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Transfer-Encoding: base64
+Content-Type: text/plain; charset=UTF-8
+
+RGVhciBDdXN0b21lciwKClRoaXMgaXMgYSB0ZXN0IG1haWwuIFBsZWFzZSBkbyBub3QgcmVwbHkg
+dG8gdGhpcy4gQWxzbyB0aGlzIGxpbmUgaXMgdmVyeSBsb25nIHNvIGl0CnNob3VsZCBiZSB3cmFw
+cGVkLgoKClRoYW5rIHlvdXIgZm9yIHlvdXIgYnVzaW5lc3MhClRoZSBnby1tYWlsIHRlYW0KCi0t
+ClRoaXMgaXMgYSBzaWduYXR1cmU=
+
+--45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7
+Content-Disposition: attachment; filename="test.attachment"
+Content-Transfer-Encoding: base64
+Content-Type; text/plain @ charset=UTF-8; $foo; bar; --invalid--
+
+VGhpcyBpcyBhIHNpbXBsZSB0ZXN0IHRleHQgZmlsZSBhdHRhY2htZW50LgoKSXQgCiAgaGFzCiAg
+ICAgc2V2ZXJhbAogICAgICAgICAgICBuZXdsaW5lcwoJICAgICAgICAgICAgYW5kCgkgICAgc3Bh
+Y2VzCiAgICAgaW4KICBpdAouCgpBcyB3ZWxsIGFzIGFuIGVtb2ppOiDwn5mCCg==
+
 --45c75ff528359022eb03679fbe91877d75343f2e1f8193e349deffa33ff7--`
 	exampleMailPlainB64WithAttachmentNoBoundary = `Date: Wed, 01 Nov 2023 00:00:00 +0000
 MIME-Version: 1.0
@@ -578,6 +760,39 @@ Content-Disposition: attachment;
  filename="testfile.txt"
 
 VGhpcyBpcyBhIHRlc3QgaW4gQmFzZTY0
+--------------26A45336F6C6196BD8BBA2A2--`
+	exampleMultiPart7BitBase64BrokenB64 = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail // 7bit with base64 attachment
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Cc: <go-mail+cc@go-mail.dev>
+Content-Type: multipart/mixed;
+ boundary="------------26A45336F6C6196BD8BBA2A2"
+
+This is a multi-part message in MIME format.
+--------------26A45336F6C6196BD8BBA2A2
+Content-Type: text/plain; charset=US-ASCII; format=flowed
+Content-Transfer-Encoding: 7bit
+
+testtest
+testtest
+testtest
+testtest
+testtest
+testtest
+
+--------------26A45336F6C6196BD8BBA2A2
+Content-Type: text/plain; charset=UTF-8;
+ name="testfile.txt"
+Content-Transfer-Encoding: base64
+Content-Disposition: attachment;
+ filename="testfile.txt"
+
+VGh@@@@§§§§hIHRlc3QgaW4gQmFzZTY0
 --------------26A45336F6C6196BD8BBA2A2--`
 	exampleMultiPart8BitBase64 = `Date: Wed, 01 Nov 2023 00:00:00 +0000
 MIME-Version: 1.0
@@ -612,8 +827,352 @@ Content-Disposition: attachment;
 
 VGhpcyBpcyBhIHRlc3QgaW4gQmFzZTY0
 --------------26A45336F6C6196BD8BBA2A2--`
+	exampleMailWithInlineEmbed = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail with inline embed
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Content-Type: multipart/related; boundary="abc123"
+
+--abc123
+Content-Type: text/html; charset=UTF-8
+Content-Transfer-Encoding: quoted-printable
+
+<html>
+  <body>
+    <p>Hello,</p>
+    <p>This is an example email with an inline image:</p>
+    <img src="cid:12345@go-mail.dev" alt="Inline Image">
+    <p>Best regards,<br>The go-mail team</p>
+  </body>
+</html>
+--abc123
+Content-Type: image/png
+Content-Transfer-Encoding: base64
+Content-ID: <12345@go-mail.dev>
+Content-Disposition: inline; filename="test.png"
+
+iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVQIW2NgYGD4DwABBAEAwS2O
+UAAAAABJRU5ErkJggg==
+--abc123--`
+	exampleMailWithInlineEmbedWrongDisposition = `Date: Wed, 01 Nov 2023 00:00:00 +0000
+MIME-Version: 1.0
+Message-ID: <1305604950.683004066175.AAAAAAAAaaaaaaaaB@go-mail.dev>
+Subject: Example mail with inline embed
+User-Agent: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+X-Mailer: go-mail v0.4.1 // https://github.com/wneessen/go-mail
+From: "Toni Tester" <go-mail@go-mail.dev>
+To: <go-mail+test@go-mail.dev>
+Content-Type: multipart/related; boundary="abc123"
+
+--abc123
+Content-Type: text/html; charset=UTF-8
+Content-Transfer-Encoding: quoted-printable
+
+<html>
+  <body>
+    <p>Hello,</p>
+    <p>This is an example email with an inline image:</p>
+    <img src="cid:12345@go-mail.dev" alt="Inline Image">
+    <p>Best regards,<br>The go-mail team</p>
+  </body>
+</html>
+--abc123
+Content-Type: image/png
+Content-Transfer-Encoding: base64
+Content-ID: <12345@go-mail.dev>
+Content-Disposition: broken; filename="test.png"
+
+iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVQIW2NgYGD4DwABBAEAwS2O
+UAAAAABJRU5ErkJggg==
+--abc123--`
 )
 
+func TestEMLToMsgFromReader(t *testing.T) {
+	t.Run("EMLToMsgFromReader via EMLToMsgFromString, check subject and encoding", func(t *testing.T) {
+		tests := []struct {
+			name         string
+			emlString    string
+			wantEncoding Encoding
+			wantSubject  string
+		}{
+			{
+				"RFC5322 A1.1 example mail", exampleMailRFC5322A11, EncodingUSASCII,
+				"Saying Hello",
+			},
+			{
+				"Plain text no encoding (7bit)", exampleMailPlain7Bit, EncodingUSASCII,
+				"Example mail // plain text without encoding",
+			},
+			{
+				"Plain text no encoding", exampleMailPlainNoEnc, NoEncoding,
+				"Example mail // plain text without encoding",
+			},
+			{
+				"Plain text quoted-printable", exampleMailPlainQP, EncodingQP,
+				"Example mail // plain text quoted-printable",
+			},
+			{
+				"Plain text base64", exampleMailPlainB64, EncodingB64,
+				"Example mail // plain text base64",
+			},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				parsed, err := EMLToMsgFromString(tt.emlString)
+				if err != nil {
+					t.Fatalf("failed to parse EML string: %s", err)
+				}
+				if parsed.Encoding() != tt.wantEncoding.String() {
+					t.Errorf("failed to parse EML string: want encoding %s, got %s", tt.wantEncoding,
+						parsed.Encoding())
+				}
+				gotSubject, ok := parsed.genHeader[HeaderSubject]
+				if !ok {
+					t.Fatalf("failed to parse EML string. No subject header found")
+				}
+				if len(gotSubject) != 1 {
+					t.Fatalf("failed to parse EML string, more than one subject header found")
+				}
+				if !strings.EqualFold(gotSubject[0], tt.wantSubject) {
+					t.Errorf("failed to parse EML string: want subject %s, got %s", tt.wantSubject,
+						gotSubject[0])
+				}
+			})
+		}
+	})
+	t.Run("EMLToMsgFromReader fails on reader", func(t *testing.T) {
+		emlReader := bytes.NewBufferString("invalid")
+		if _, err := EMLToMsgFromReader(emlReader); err == nil {
+			t.Errorf("EML parsing with invalid EML string should fail")
+		}
+	})
+	t.Run("EMLToMsgFromReader fails on parseEML", func(t *testing.T) {
+		emlReader := bytes.NewBufferString(exampleMailRFC5322A11InvalidFrom)
+		if _, err := EMLToMsgFromReader(emlReader); err == nil {
+			t.Errorf("EML parsing with invalid EML string should fail")
+		}
+	})
+	t.Run("EMLToMsgFromReader via EMLToMsgFromString on different examples", func(t *testing.T) {
+		tests := []struct {
+			name       string
+			emlString  string
+			shouldFail bool
+		}{
+			{
+				name:       "Valid RFC 5322 Example",
+				emlString:  exampleMailRFC5322A11,
+				shouldFail: false,
+			},
+			{
+				name:       "Invalid From Header (RFC 5322)",
+				emlString:  exampleMailRFC5322A11InvalidFrom,
+				shouldFail: true,
+			},
+			{
+				name:       "Invalid Header",
+				emlString:  exampleMailInvalidHeader,
+				shouldFail: true,
+			},
+			{
+				name:       "Plain broken Content-Type",
+				emlString:  exampleMailInvalidContentType,
+				shouldFail: true,
+			},
+			{
+				name:       "Plain No Encoding",
+				emlString:  exampleMailPlainNoEnc,
+				shouldFail: false,
+			},
+			{
+				name:       "Plain invalid CTE",
+				emlString:  exampleMailPlainInvalidCTE,
+				shouldFail: true,
+			},
+			{
+				name:       "Plain 7bit",
+				emlString:  exampleMailPlain7Bit,
+				shouldFail: false,
+			},
+			{
+				name:       "Broken Body Base64",
+				emlString:  exampleMailPlainBrokenBody,
+				shouldFail: true,
+			},
+			{
+				name:       "Unknown Content Type",
+				emlString:  exampleMailPlainUnknownContentType,
+				shouldFail: true,
+			},
+			{
+				name:       "Broken Header",
+				emlString:  exampleMailPlainBrokenHeader,
+				shouldFail: true,
+			},
+			{
+				name:       "Broken From Header",
+				emlString:  exampleMailPlainBrokenFrom,
+				shouldFail: true,
+			},
+			{
+				name:       "Broken To Header",
+				emlString:  exampleMailPlainBrokenTo,
+				shouldFail: true,
+			},
+			{
+				name:       "Invalid Date",
+				emlString:  exampleMailPlainNoEncInvalidDate,
+				shouldFail: true,
+			},
+			{
+				name:       "No Date Header",
+				emlString:  exampleMailPlainNoEncNoDate,
+				shouldFail: false,
+			},
+			{
+				name:       "Quoted Printable Encoding",
+				emlString:  exampleMailPlainQP,
+				shouldFail: false,
+			},
+			{
+				name:       "Unsupported Transfer Encoding",
+				emlString:  exampleMailPlainUnsupportedTransferEnc,
+				shouldFail: true,
+			},
+			{
+				name:       "Base64 Encoding",
+				emlString:  exampleMailPlainB64,
+				shouldFail: false,
+			},
+			{
+				name:       "Base64 with Attachment",
+				emlString:  exampleMailPlainB64WithAttachment,
+				shouldFail: false,
+			},
+			{
+				name:       "Base64 with Attachment no content types",
+				emlString:  exampleMailPlainB64WithAttachmentNoContentType,
+				shouldFail: true,
+			},
+			{
+				name:       "Multipart Base64 with Attachment broken Base64",
+				emlString:  exampleMailPlainB64WithAttachmentBrokenB64,
+				shouldFail: true,
+			},
+			{
+				name:       "Base64 with Attachment with invalid content type in attachment",
+				emlString:  exampleMailPlainB64WithAttachmentInvalidContentType,
+				shouldFail: true,
+			},
+			{
+				name:       "Base64 with Attachment with invalid CTE in attachment",
+				emlString:  exampleMailPlainB64WithAttachmentInvalidCTE,
+				shouldFail: true,
+			},
+			{
+				name:       "Base64 with Attachment No Boundary",
+				emlString:  exampleMailPlainB64WithAttachmentNoBoundary,
+				shouldFail: true,
+			},
+			{
+				name:       "Broken Body Base64",
+				emlString:  exampleMailPlainB64BrokenBody,
+				shouldFail: true,
+			},
+			{
+				name:       "Base64 with Embedded Image",
+				emlString:  exampleMailPlainB64WithEmbed,
+				shouldFail: false,
+			},
+			{
+				name:       "Base64 with Embed No Content-ID",
+				emlString:  exampleMailPlainB64WithEmbedNoContentID,
+				shouldFail: false,
+			},
+			{
+				name:       "Multipart Mixed with Attachment, Embed, and Alternative Part",
+				emlString:  exampleMailMultipartMixedAlternativeRelated,
+				shouldFail: false,
+			},
+			{
+				name:       "Multipart 7bit Base64",
+				emlString:  exampleMultiPart7BitBase64,
+				shouldFail: false,
+			},
+			{
+				name:       "Multipart 7bit Base64 with broken Base64",
+				emlString:  exampleMultiPart7BitBase64BrokenB64,
+				shouldFail: true,
+			},
+			{
+				name:       "Multipart 8bit Base64",
+				emlString:  exampleMultiPart8BitBase64,
+				shouldFail: false,
+			},
+			{
+				name:       "Multipart with inline embed",
+				emlString:  exampleMailWithInlineEmbed,
+				shouldFail: false,
+			},
+			{
+				name:       "Multipart with inline embed disposition broken",
+				emlString:  exampleMailWithInlineEmbedWrongDisposition,
+				shouldFail: true,
+			},
+		}
+
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				_, err := EMLToMsgFromString(tt.emlString)
+				if tt.shouldFail && err == nil {
+					t.Errorf("parsing of EML was supposed to fail, but it did not")
+				}
+				if !tt.shouldFail && err != nil {
+					t.Errorf("parsing of EML failed: %s", err)
+				}
+			})
+		}
+	})
+}
+
+func TestEMLToMsgFromFile(t *testing.T) {
+	t.Run("EMLToMsgFromFile succeeds", func(t *testing.T) {
+		parsed, err := EMLToMsgFromFile("testdata/RFC5322-A1-1.eml")
+		if err != nil {
+			t.Fatalf("EMLToMsgFromFile failed: %s ", err)
+		}
+		if parsed.Encoding() != EncodingUSASCII.String() {
+			t.Errorf("EMLToMsgFromFile failed: want encoding %s, got %s", EncodingUSASCII,
+				parsed.Encoding())
+		}
+		gotSubject, ok := parsed.genHeader[HeaderSubject]
+		if !ok {
+			t.Fatalf("failed to parse EML string. No subject header found")
+		}
+		if len(gotSubject) != 1 {
+			t.Fatalf("failed to parse EML string, more than one subject header found")
+		}
+		if !strings.EqualFold(gotSubject[0], "Saying Hello") {
+			t.Errorf("failed to parse EML string: want subject %s, got %s", "Saying Hello",
+				gotSubject[0])
+		}
+	})
+	t.Run("EMLToMsgFromFile fails on file not found", func(t *testing.T) {
+		if _, err := EMLToMsgFromFile("testdata/not-existing.eml"); err == nil {
+			t.Errorf("EMLToMsgFromFile with invalid file should fail")
+		}
+	})
+	t.Run("EMLToMsgFromFile fails on parseEML", func(t *testing.T) {
+		if _, err := EMLToMsgFromFile("testdata/RFC5322-A1-1-invalid-from.eml"); err == nil {
+			t.Errorf("EMLToMsgFromFile with invalid EML message should fail")
+		}
+	})
+}
+
+/*
 func TestEMLToMsgFromString(t *testing.T) {
 	tests := []struct {
 		name string
@@ -621,26 +1180,6 @@ func TestEMLToMsgFromString(t *testing.T) {
 		enc  string
 		sub  string
 	}{
-		{
-			"RFC5322 A1.1", exampleMailRFC5322A11, "7bit",
-			"Saying Hello",
-		},
-		{
-			"Plain text no encoding (7bit)", exampleMailPlain7Bit, "7bit",
-			"Example mail // plain text without encoding",
-		},
-		{
-			"Plain text no encoding", exampleMailPlainNoEnc, "8bit",
-			"Example mail // plain text without encoding",
-		},
-		{
-			"Plain text quoted-printable", exampleMailPlainQP, "quoted-printable",
-			"Example mail // plain text quoted-printable",
-		},
-		{
-			"Plain text base64", exampleMailPlainB64, "base64",
-			"Example mail // plain text base64",
-		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
@@ -1009,3 +1548,6 @@ func stringToTempFile(data, name string) (string, string, error) {
 	}
 	return tempDir, filePath, nil
 }
+
+
+*/

file_test.go

@@ -6,134 +6,183 @@ package mail
 
 import "testing"
 
-// TestFile_SetGetHeader tests the set-/getHeader method of the File object
-func TestFile_SetGetHeader(t *testing.T) {
-	f := File{
-		Name:   "testfile.txt",
-		Header: make(map[string][]string),
-	}
-	f.setHeader(HeaderContentType, "text/plain")
-	fi, ok := f.getHeader(HeaderContentType)
-	if !ok {
-		t.Errorf("getHeader method of File did not return a value")
-		return
-	}
-	if fi != "text/plain" {
-		t.Errorf("getHeader returned wrong value. Expected: %s, got: %s", "text/plain", fi)
-	}
-	fi, ok = f.getHeader(HeaderContentTransferEnc)
-	if ok {
-		t.Errorf("getHeader method of File did return a value, but wasn't supposed to")
-		return
-	}
-	if fi != "" {
-		t.Errorf("getHeader returned wrong value. Expected: %s, got: %s", "", fi)
-	}
-}
-
-// TestFile_WithFileDescription tests the WithFileDescription option
-func TestFile_WithFileDescription(t *testing.T) {
-	tests := []struct {
-		name string
-		desc string
-	}{
-		{"File description: test", "test"},
-		{"File description: empty", ""},
-	}
-	for _, tt := range tests {
-		m := NewMsg()
-		t.Run(tt.name, func(t *testing.T) {
-			m.AttachFile("file.go", WithFileDescription(tt.desc))
-			al := m.GetAttachments()
-			if len(al) <= 0 {
-				t.Errorf("AttachFile() failed. Attachment list is empty")
-			}
-			a := al[0]
-			if a.Desc != tt.desc {
-				t.Errorf("WithFileDescription() failed. Expected: %s, got: %s", tt.desc, a.Desc)
-			}
-		})
-	}
-}
-
-// TestFile_WithContentID tests the WithFileContentID option
-func TestFile_WithContentID(t *testing.T) {
-	tests := []struct {
-		name      string
-		contentid string
-	}{
-		{"File Content-ID: test", "test"},
-		{"File Content-ID: empty", ""},
-	}
-	for _, tt := range tests {
-		m := NewMsg()
-		t.Run(tt.name, func(t *testing.T) {
-			m.AttachFile("file.go", WithFileContentID(tt.contentid))
-			al := m.GetAttachments()
-			if len(al) <= 0 {
-				t.Errorf("AttachFile() failed. Attachment list is empty")
-			}
-			a := al[0]
-			if a.Header.Get(HeaderContentID.String()) != tt.contentid {
-				t.Errorf("WithFileContentID() failed. Expected: %s, got: %s", tt.contentid,
-					a.Header.Get(HeaderContentID.String()))
-			}
-		})
-	}
-}
-
-// TestFile_WithFileEncoding tests the WithFileEncoding option
-func TestFile_WithFileEncoding(t *testing.T) {
-	tests := []struct {
-		name string
-		enc  Encoding
-		want Encoding
-	}{
-		{"File encoding: 8bit raw", NoEncoding, NoEncoding},
-		{"File encoding: Base64", EncodingB64, EncodingB64},
-		{"File encoding: quoted-printable (not allowed)", EncodingQP, ""},
-	}
-	for _, tt := range tests {
-		m := NewMsg()
-		t.Run(tt.name, func(t *testing.T) {
-			m.AttachFile("file.go", WithFileEncoding(tt.enc))
-			al := m.GetAttachments()
-			if len(al) <= 0 {
-				t.Errorf("AttachFile() failed. Attachment list is empty")
-			}
-			a := al[0]
-			if a.Enc != tt.want {
-				t.Errorf("WithFileEncoding() failed. Expected: %s, got: %s", tt.enc, a.Enc)
-			}
-		})
-	}
-}
-
-// TestFile_WithFileContentType tests the WithFileContentType option
-func TestFile_WithFileContentType(t *testing.T) {
-	tests := []struct {
-		name string
-		ct   ContentType
-		want string
-	}{
-		{"File content-type: text/plain", TypeTextPlain, "text/plain"},
-		{"File content-type: html/html", TypeTextHTML, "text/html"},
-		{"File content-type: application/octet-stream", TypeAppOctetStream, "application/octet-stream"},
-		{"File content-type: application/pgp-encrypted", TypePGPEncrypted, "application/pgp-encrypted"},
-		{"File content-type: application/pgp-signature", TypePGPSignature, "application/pgp-signature"},
-	}
-	for _, tt := range tests {
-		m := NewMsg()
-		t.Run(tt.name, func(t *testing.T) {
-			m.AttachFile("file.go", WithFileContentType(tt.ct))
-			al := m.GetAttachments()
-			if len(al) <= 0 {
-				t.Errorf("AttachFile() failed. Attachment list is empty")
-			}
-			a := al[0]
-			if a.ContentType != ContentType(tt.want) {
-				t.Errorf("WithFileContentType() failed. Expected: %s, got: %s", tt.want, a.ContentType)
-			}
-		})
-	}
+func TestFile(t *testing.T) {
+	t.Run("setHeader", func(t *testing.T) {
+		f := File{
+			Name:   "testfile.txt",
+			Header: make(map[string][]string),
+		}
+		f.setHeader(HeaderContentType, "text/plain")
+		contentType, ok := f.Header[HeaderContentType.String()]
+		if !ok {
+			t.Fatalf("setHeader failed. Expected header %s to be set", HeaderContentType)
+		}
+		if len(contentType) != 1 {
+			t.Fatalf("setHeader failed. Expected header %s to have one value, got: %d", HeaderContentType,
+				len(contentType))
+		}
+		if contentType[0] != "text/plain" {
+			t.Fatalf("setHeader failed. Expected header %s to have value %s, got: %s",
+				HeaderContentType.String(), "text/plain", contentType[0])
+		}
+	})
+	t.Run("getHeader", func(t *testing.T) {
+		f := File{
+			Name:   "testfile.txt",
+			Header: make(map[string][]string),
+		}
+		f.setHeader(HeaderContentType, "text/plain")
+		contentType, ok := f.getHeader(HeaderContentType)
+		if !ok {
+			t.Fatalf("setHeader failed. Expected header %s to be set", HeaderContentType)
+		}
+		if contentType != "text/plain" {
+			t.Fatalf("setHeader failed. Expected header %s to have value %s, got: %s",
+				HeaderContentType.String(), "text/plain", contentType)
+		}
+	})
+	t.Run("WithFileDescription", func(t *testing.T) {
+		tests := []struct {
+			name string
+			desc string
+		}{
+			{"File description: test", "test"},
+			{"File description: with newline", "test\n"},
+			{"File description: empty", ""},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				message := NewMsg()
+				message.AttachFile("file.go", WithFileDescription(tt.desc))
+				attachments := message.GetAttachments()
+				if len(attachments) <= 0 {
+					t.Fatalf("failed to retrieve attachments list")
+				}
+				firstAttachment := attachments[0]
+				if firstAttachment == nil {
+					t.Fatalf("failed to retrieve first attachment, got nil")
+				}
+				if firstAttachment.Desc != tt.desc {
+					t.Errorf("WithFileDescription() failed. Expected: %s, got: %s", tt.desc,
+						firstAttachment.Desc)
+				}
+			})
+		}
+	})
+	t.Run("WithFileContentID", func(t *testing.T) {
+		tests := []struct {
+			name string
+			id   string
+		}{
+			{"Content-ID: test", "test"},
+			{"Content-ID: with newline", "test\n"},
+			{"Content-ID: empty", ""},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				message := NewMsg()
+				message.AttachFile("file.go", WithFileContentID(tt.id))
+				attachments := message.GetAttachments()
+				if len(attachments) <= 0 {
+					t.Fatalf("failed to retrieve attachments list")
+				}
+				firstAttachment := attachments[0]
+				if firstAttachment == nil {
+					t.Fatalf("failed to retrieve first attachment, got nil")
+				}
+				contentID := firstAttachment.Header.Get(HeaderContentID.String())
+				if contentID != tt.id {
+					t.Errorf("WithFileContentID() failed. Expected: %s, got: %s", tt.id,
+						contentID)
+				}
+			})
+		}
+	})
+	t.Run("WithFileEncoding", func(t *testing.T) {
+		tests := []struct {
+			name     string
+			encoding Encoding
+			want     Encoding
+		}{
+			{"File encoding: US-ASCII", EncodingUSASCII, EncodingUSASCII},
+			{"File encoding: 8bit raw", NoEncoding, NoEncoding},
+			{"File encoding: Base64", EncodingB64, EncodingB64},
+			{"File encoding: quoted-printable (not allowed)", EncodingQP, ""},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				message := NewMsg()
+				message.AttachFile("file.go", WithFileEncoding(tt.encoding))
+				attachments := message.GetAttachments()
+				if len(attachments) <= 0 {
+					t.Fatalf("failed to retrieve attachments list")
+				}
+				firstAttachment := attachments[0]
+				if firstAttachment == nil {
+					t.Fatalf("failed to retrieve first attachment, got nil")
+				}
+				if firstAttachment.Enc != tt.want {
+					t.Errorf("WithFileEncoding() failed. Expected: %s, got: %s", tt.want, firstAttachment.Enc)
+				}
+			})
+		}
+	})
+	t.Run("WithFileName", func(t *testing.T) {
+		tests := []struct {
+			name     string
+			fileName string
+		}{
+			{"File name: test", "test"},
+			{"File name: with newline", "test\n"},
+			{"File name: empty", ""},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				message := NewMsg()
+				message.AttachFile("file.go", WithFileName(tt.fileName))
+				attachments := message.GetAttachments()
+				if len(attachments) <= 0 {
+					t.Fatalf("failed to retrieve attachments list")
+				}
+				firstAttachment := attachments[0]
+				if firstAttachment == nil {
+					t.Fatalf("failed to retrieve first attachment, got nil")
+				}
+				if firstAttachment.Name != tt.fileName {
+					t.Errorf("WithFileName() failed. Expected: %s, got: %s", tt.fileName,
+						firstAttachment.Name)
+				}
+			})
+		}
+	})
+	t.Run("WithFileContentType", func(t *testing.T) {
+		tests := []struct {
+			name        string
+			contentType ContentType
+		}{
+			{"File content-type: text/plain", TypeTextPlain},
+			{"File content-type: html/html", TypeTextHTML},
+			{"File content-type: application/octet-stream", TypeAppOctetStream},
+			{"File content-type: application/pgp-encrypted", TypePGPEncrypted},
+			{"File content-type: application/pgp-signature", TypePGPSignature},
+		}
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				message := NewMsg()
+				message.AttachFile("file.go", WithFileContentType(tt.contentType))
+				attachments := message.GetAttachments()
+				if len(attachments) <= 0 {
+					t.Fatalf("failed to retrieve attachments list")
+				}
+				firstAttachment := attachments[0]
+				if firstAttachment == nil {
+					t.Fatalf("failed to retrieve first attachment, got nil")
+				}
+				if firstAttachment.ContentType != tt.contentType {
+					t.Errorf("WithFileContentType() failed. Expected: %s, got: %s", tt.contentType,
+						firstAttachment.ContentType)
+				}
+			})
+		}
+	})
 }

header_test.go

@@ -8,69 +8,13 @@ import (
 	"testing"
 )
 
-// TestImportance_StringFuncs tests the different string method of the Importance object
-func TestImportance_StringFuncs(t *testing.T) {
-	tests := []struct {
+var (
+	genHeaderTests = []struct {
 		name   string
-		imp    Importance
-		wantns string
-		xprio  string
+		header Header
 		want   string
 	}{
-		{"Importance: Non-Urgent", ImportanceNonUrgent, "0", "5", "non-urgent"},
-		{"Importance: Low", ImportanceLow, "0", "5", "low"},
-		{"Importance: Normal", ImportanceNormal, "", "", ""},
-		{"Importance: High", ImportanceHigh, "1", "1", "high"},
-		{"Importance: Urgent", ImportanceUrgent, "1", "1", "urgent"},
-		{"Importance: Unknown", 9, "", "", ""},
-	}
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			if tt.imp.NumString() != tt.wantns {
-				t.Errorf("wrong number string for Importance returned. Expected: %s, got: %s",
-					tt.wantns, tt.imp.NumString())
-			}
-			if tt.imp.XPrioString() != tt.xprio {
-				t.Errorf("wrong x-prio string for Importance returned. Expected: %s, got: %s",
-					tt.xprio, tt.imp.XPrioString())
-			}
-			if tt.imp.String() != tt.want {
-				t.Errorf("wrong string for Importance returned. Expected: %s, got: %s",
-					tt.want, tt.imp.String())
-			}
-		})
-	}
-}
-
-// TestAddrHeader_String tests the string method of the AddrHeader object
-func TestAddrHeader_String(t *testing.T) {
-	tests := []struct {
-		name string
-		ah   AddrHeader
-		want string
-	}{
-		{"Address header: From", HeaderFrom, "From"},
-		{"Address header: To", HeaderTo, "To"},
-		{"Address header: Cc", HeaderCc, "Cc"},
-		{"Address header: Bcc", HeaderBcc, "Bcc"},
-	}
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			if tt.ah.String() != tt.want {
-				t.Errorf("wrong string for AddrHeader returned. Expected: %s, got: %s",
-					tt.want, tt.ah.String())
-			}
-		})
-	}
-}
-
-// TestHeader_String tests the string method of the Header object
-func TestHeader_String(t *testing.T) {
-	tests := []struct {
-		name string
-		h    Header
-		want string
-	}{
+		{"Header: Content-Description", HeaderContentDescription, "Content-Description"},
 		{"Header: Content-Disposition", HeaderContentDisposition, "Content-Disposition"},
 		{"Header: Content-ID", HeaderContentID, "Content-ID"},
 		{"Header: Content-Language", HeaderContentLang, "Content-Language"},
@@ -78,6 +22,10 @@ func TestHeader_String(t *testing.T) {
 		{"Header: Content-Transfer-Encoding", HeaderContentTransferEnc, "Content-Transfer-Encoding"},
 		{"Header: Content-Type", HeaderContentType, "Content-Type"},
 		{"Header: Date", HeaderDate, "Date"},
+		{
+			"Header: Disposition-Notification-To", HeaderDispositionNotificationTo,
+			"Disposition-Notification-To",
+		},
 		{"Header: Importance", HeaderImportance, "Importance"},
 		{"Header: In-Reply-To", HeaderInReplyTo, "In-Reply-To"},
 		{"Header: List-Unsubscribe", HeaderListUnsubscribe, "List-Unsubscribe"},
@@ -87,19 +35,90 @@ func TestHeader_String(t *testing.T) {
 		{"Header: Organization", HeaderOrganization, "Organization"},
 		{"Header: Precedence", HeaderPrecedence, "Precedence"},
 		{"Header: Priority", HeaderPriority, "Priority"},
-		{"Header: HeaderReferences", HeaderReferences, "References"},
+		{"Header: References", HeaderReferences, "References"},
 		{"Header: Reply-To", HeaderReplyTo, "Reply-To"},
 		{"Header: Subject", HeaderSubject, "Subject"},
 		{"Header: User-Agent", HeaderUserAgent, "User-Agent"},
+		{"Header: X-Auto-Response-Suppress", HeaderXAutoResponseSuppress, "X-Auto-Response-Suppress"},
 		{"Header: X-Mailer", HeaderXMailer, "X-Mailer"},
 		{"Header: X-MSMail-Priority", HeaderXMSMailPriority, "X-MSMail-Priority"},
 		{"Header: X-Priority", HeaderXPriority, "X-Priority"},
 	}
-	for _, tt := range tests {
+	addrHeaderTests = []struct {
+		name   string
+		header AddrHeader
+		want   string
+	}{
+		{"From", HeaderFrom, "From"},
+		{"To", HeaderTo, "To"},
+		{"Cc", HeaderCc, "Cc"},
+		{"Bcc", HeaderBcc, "Bcc"},
+	}
+)
+
+func TestImportance_Stringer(t *testing.T) {
+	tests := []struct {
+		name    string
+		imp     Importance
+		wantnum string
+		xprio   string
+		want    string
+	}{
+		{"Non-Urgent", ImportanceNonUrgent, "0", "5", "non-urgent"},
+		{"Low", ImportanceLow, "0", "5", "low"},
+		{"Normal", ImportanceNormal, "", "", ""},
+		{"High", ImportanceHigh, "1", "1", "high"},
+		{"Urgent", ImportanceUrgent, "1", "1", "urgent"},
+		{"Unknown", 9, "", "", ""},
+	}
+	t.Run("String", func(t *testing.T) {
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				if tt.imp.String() != tt.want {
+					t.Errorf("wrong string for Importance returned. Expected: %s, got: %s", tt.want, tt.imp.String())
+				}
+			})
+		}
+	})
+	t.Run("NumString", func(t *testing.T) {
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				if tt.imp.NumString() != tt.wantnum {
+					t.Errorf("wrong number string for Importance returned. Expected: %s, got: %s", tt.wantnum,
+						tt.imp.NumString())
+				}
+			})
+		}
+	})
+	t.Run("XPrioString", func(t *testing.T) {
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
+				if tt.imp.XPrioString() != tt.xprio {
+					t.Errorf("wrong x-prio string for Importance returned. Expected: %s, got: %s", tt.xprio,
+						tt.imp.XPrioString())
+				}
+			})
+		}
+	})
+}
+
+func TestAddrHeader_Stringer(t *testing.T) {
+	for _, tt := range addrHeaderTests {
 		t.Run(tt.name, func(t *testing.T) {
-			if tt.h.String() != tt.want {
-				t.Errorf("wrong string for Header returned. Expected: %s, got: %s",
-					tt.want, tt.h.String())
+			if tt.header.String() != tt.want {
+				t.Errorf("wrong string for AddrHeader returned. Expected: %s, got: %s",
+					tt.want, tt.header.String())
+			}
+		})
+	}
+}
+
+func TestHeader_Stringer(t *testing.T) {
+	for _, tt := range genHeaderTests {
+		t.Run(tt.name, func(t *testing.T) {
+			if tt.header.String() != tt.want {
+				t.Errorf("wrong string for Header returned. Expected: %s, got: %s",
+					tt.want, tt.header.String())
 			}
 		})
 	}

log/jsonlog.go

@@ -41,42 +41,48 @@ func NewJSON(output io.Writer, level Level) *JSONlog {
 	}
 }
 
+// logMessage is a helper function to handle different log levels and formats.
+func logMessage(level Level, log *slog.Logger, logData Log, formatFunc func(string, ...interface{}) string) {
+	lGroup := log.WithGroup(DirString).With(
+		slog.String(DirFromString, logData.directionFrom()),
+		slog.String(DirToString, logData.directionTo()),
+	)
+	switch level {
+	case LevelDebug:
+		lGroup.Debug(formatFunc(logData.Format, logData.Messages...))
+	case LevelInfo:
+		lGroup.Info(formatFunc(logData.Format, logData.Messages...))
+	case LevelWarn:
+		lGroup.Warn(formatFunc(logData.Format, logData.Messages...))
+	case LevelError:
+		lGroup.Error(formatFunc(logData.Format, logData.Messages...))
+	}
+}
+
 // Debugf logs a debug message via the structured JSON logger
 func (l *JSONlog) Debugf(log Log) {
 	if l.level >= LevelDebug {
-		l.log.WithGroup(DirString).With(
-			slog.String(DirFromString, log.directionFrom()),
-			slog.String(DirToString, log.directionTo()),
-		).Debug(fmt.Sprintf(log.Format, log.Messages...))
+		logMessage(LevelDebug, l.log, log, fmt.Sprintf)
 	}
 }
 
 // Infof logs a info message via the structured JSON logger
 func (l *JSONlog) Infof(log Log) {
 	if l.level >= LevelInfo {
-		l.log.WithGroup(DirString).With(
-			slog.String(DirFromString, log.directionFrom()),
-			slog.String(DirToString, log.directionTo()),
-		).Info(fmt.Sprintf(log.Format, log.Messages...))
+		logMessage(LevelInfo, l.log, log, fmt.Sprintf)
 	}
 }
 
 // Warnf logs a warn message via the structured JSON logger
 func (l *JSONlog) Warnf(log Log) {
 	if l.level >= LevelWarn {
-		l.log.WithGroup(DirString).With(
-			slog.String(DirFromString, log.directionFrom()),
-			slog.String(DirToString, log.directionTo()),
-		).Warn(fmt.Sprintf(log.Format, log.Messages...))
+		logMessage(LevelWarn, l.log, log, fmt.Sprintf)
 	}
 }
 
 // Errorf logs a warn message via the structured JSON logger
 func (l *JSONlog) Errorf(log Log) {
 	if l.level >= LevelError {
-		l.log.WithGroup(DirString).With(
-			slog.String(DirFromString, log.directionFrom()),
-			slog.String(DirToString, log.directionTo()),
-		).Error(fmt.Sprintf(log.Format, log.Messages...))
+		logMessage(LevelError, l.log, log, fmt.Sprintf)
 	}
 }

log/stdlog.go

@@ -35,34 +35,36 @@ func New(output io.Writer, level Level) *Stdlog {
 	}
 }
 
+// logStdMessage is a helper function to handle different log levels and formats for Stdlog.
+func logStdMessage(logger *log.Logger, logData Log, callDepth int) {
+	format := fmt.Sprintf("%s %s", logData.directionPrefix(), logData.Format)
+	_ = logger.Output(callDepth, fmt.Sprintf(format, logData.Messages...))
+}
+
 // Debugf performs a Printf() on the debug logger
 func (l *Stdlog) Debugf(log Log) {
 	if l.level >= LevelDebug {
-		format := fmt.Sprintf("%s %s", log.directionPrefix(), log.Format)
-		_ = l.debug.Output(CallDepth, fmt.Sprintf(format, log.Messages...))
+		logStdMessage(l.debug, log, CallDepth)
 	}
 }
 
 // Infof performs a Printf() on the info logger
 func (l *Stdlog) Infof(log Log) {
 	if l.level >= LevelInfo {
-		format := fmt.Sprintf("%s %s", log.directionPrefix(), log.Format)
-		_ = l.info.Output(CallDepth, fmt.Sprintf(format, log.Messages...))
+		logStdMessage(l.info, log, CallDepth)
 	}
 }
 
 // Warnf performs a Printf() on the warn logger
 func (l *Stdlog) Warnf(log Log) {
 	if l.level >= LevelWarn {
-		format := fmt.Sprintf("%s %s", log.directionPrefix(), log.Format)
-		_ = l.warn.Output(CallDepth, fmt.Sprintf(format, log.Messages...))
+		logStdMessage(l.warn, log, CallDepth)
 	}
 }
 
 // Errorf performs a Printf() on the error logger
 func (l *Stdlog) Errorf(log Log) {
 	if l.level >= LevelError {
-		format := fmt.Sprintf("%s %s", log.directionPrefix(), log.Format)
-		_ = l.err.Output(CallDepth, fmt.Sprintf(format, log.Messages...))
+		logStdMessage(l.err, log, CallDepth)
 	}
 }

msg.go

@@ -367,23 +367,45 @@ func (m *Msg) SignWithTLSCertificate(keyPairTlS *tls.Certificate) error {
 		return fmt.Errorf("failed to parse intermediate certificate: %w", err)
 	}
 
+	leafCertificate, err := getLeafCertificate(keyPairTlS)
+	if err != nil {
+		return fmt.Errorf("failed to get leaf certificate: %w", err)
+	}
+
 	switch keyPairTlS.PrivateKey.(type) {
 	case *rsa.PrivateKey:
 		if intermediateCertificate == nil {
-			return m.SignWithSMimeRSA(keyPairTlS.PrivateKey.(*rsa.PrivateKey), keyPairTlS.Leaf, nil)
+			return m.SignWithSMimeRSA(keyPairTlS.PrivateKey.(*rsa.PrivateKey), leafCertificate, nil)
 		}
-		return m.SignWithSMimeRSA(keyPairTlS.PrivateKey.(*rsa.PrivateKey), keyPairTlS.Leaf, intermediateCertificate)
+		return m.SignWithSMimeRSA(keyPairTlS.PrivateKey.(*rsa.PrivateKey), leafCertificate, intermediateCertificate)
 
 	case *ecdsa.PrivateKey:
 		if intermediateCertificate == nil {
-			return m.SignWithSMimeECDSA(keyPairTlS.PrivateKey.(*ecdsa.PrivateKey), keyPairTlS.Leaf, nil)
+			return m.SignWithSMimeECDSA(keyPairTlS.PrivateKey.(*ecdsa.PrivateKey), leafCertificate, nil)
 		}
-		return m.SignWithSMimeECDSA(keyPairTlS.PrivateKey.(*ecdsa.PrivateKey), keyPairTlS.Leaf, intermediateCertificate)
+		return m.SignWithSMimeECDSA(keyPairTlS.PrivateKey.(*ecdsa.PrivateKey), leafCertificate, intermediateCertificate)
 	default:
 		return fmt.Errorf("unsupported private key type: %T", keyPairTlS.PrivateKey)
 	}
 }
 
+// getLeafCertificate returns the leaf certificate from a tls.Certificate.
+// PLEASE NOTE: Before Go 1.23 Certificate.Leaf was left nil, and the parsed certificate was
+// discarded. This behavior can be re-enabled by setting "x509keypairleaf=0"
+// in the GODEBUG environment variable.
+func getLeafCertificate(keyPairTlS *tls.Certificate) (*x509.Certificate, error) {
+	if keyPairTlS.Leaf != nil {
+		return keyPairTlS.Leaf, nil
+	}
+
+	cert, err := x509.ParseCertificate(keyPairTlS.Certificate[0])
+	if err != nil {
+		return nil, err
+	}
+
+	return cert, nil
+}
+
 // This method allows you to specify a character set for the email message. The charset is
 // important for ensuring that the content of the message is correctly interpreted by
 // mail clients. Common charset values include UTF-8, ISO-8859-1, and others. If a charset
@@ -632,6 +654,9 @@ func (m *Msg) SetAddrHeader(header AddrHeader, values ...string) error {
 // References:
 //   - https://datatracker.ietf.org/doc/html/rfc5322#section-3.4
 func (m *Msg) SetAddrHeaderIgnoreInvalid(header AddrHeader, values ...string) {
+	if m.addrHeader == nil {
+		m.addrHeader = make(map[AddrHeader][]*mail.Address)
+	}
 	var addresses []*mail.Address
 	for _, addrVal := range values {
 		address, err := mail.ParseAddress(m.encodeString(addrVal))
@@ -640,7 +665,14 @@ func (m *Msg) SetAddrHeaderIgnoreInvalid(header AddrHeader, values ...string) {
 		}
 		addresses = append(addresses, address)
 	}
-	m.addrHeader[header] = addresses
+	switch header {
+	case HeaderFrom:
+		if len(addresses) > 0 {
+			m.addrHeader[header] = []*mail.Address{addresses[0]}
+		}
+	default:
+		m.addrHeader[header] = addresses
+	}
 }
 
 // EnvelopeFrom sets the envelope from address for the Msg.
@@ -792,7 +824,16 @@ func (m *Msg) ToIgnoreInvalid(rcpts ...string) {
 // References:
 //   - https://datatracker.ietf.org/doc/html/rfc5322#section-3.6.3
 func (m *Msg) ToFromString(rcpts string) error {
-	return m.To(strings.Split(rcpts, ",")...)
+	src := strings.Split(rcpts, ",")
+	var dst []string
+	for _, address := range src {
+		address = strings.TrimSpace(address)
+		if address == "" {
+			continue
+		}
+		dst = append(dst, address)
+	}
+	return m.To(dst...)
 }
 
 // Cc sets one or more "CC" (carbon copy) addresses in the mail body for the Msg.
@@ -877,7 +918,16 @@ func (m *Msg) CcIgnoreInvalid(rcpts ...string) {
 // References:
 //   - https://datatracker.ietf.org/doc/html/rfc5322#section-3.6.3
 func (m *Msg) CcFromString(rcpts string) error {
-	return m.Cc(strings.Split(rcpts, ",")...)
+	src := strings.Split(rcpts, ",")
+	var dst []string
+	for _, address := range src {
+		address = strings.TrimSpace(address)
+		if address == "" {
+			continue
+		}
+		dst = append(dst, address)
+	}
+	return m.Cc(dst...)
 }
 
 // Bcc sets one or more "BCC" (blind carbon copy) addresses in the mail body for the Msg.
@@ -963,7 +1013,16 @@ func (m *Msg) BccIgnoreInvalid(rcpts ...string) {
 // References:
 //   - https://datatracker.ietf.org/doc/html/rfc5322#section-3.6.3
 func (m *Msg) BccFromString(rcpts string) error {
-	return m.Bcc(strings.Split(rcpts, ",")...)
+	src := strings.Split(rcpts, ",")
+	var dst []string
+	for _, address := range src {
+		address = strings.TrimSpace(address)
+		if address == "" {
+			continue
+		}
+		dst = append(dst, address)
+	}
+	return m.Bcc(dst...)
 }
 
 // ReplyTo sets the "Reply-To" address for the Msg, specifying where replies should be sent.
@@ -1099,8 +1158,7 @@ func (m *Msg) SetBulk() {
 //   - https://datatracker.ietf.org/doc/html/rfc5322#section-3.3
 //   - https://datatracker.ietf.org/doc/html/rfc1123
 func (m *Msg) SetDate() {
-	now := time.Now().Format(time.RFC1123Z)
-	m.SetGenHeader(HeaderDate, now)
+	m.SetDateWithValue(time.Now())
 }
 
 // SetDateWithValue sets the "Date" header for the Msg using the provided time value in a valid RFC 1123 format.
@@ -1200,6 +1258,9 @@ func (m *Msg) IsDelivered() bool {
 // References:
 //   - https://datatracker.ietf.org/doc/html/rfc8098
 func (m *Msg) RequestMDNTo(rcpts ...string) error {
+	if m.genHeader == nil {
+		m.genHeader = make(map[Header][]string)
+	}
 	var addresses []string
 	for _, addrVal := range rcpts {
 		address, err := mail.ParseAddress(addrVal)
@@ -1208,9 +1269,7 @@ func (m *Msg) RequestMDNTo(rcpts ...string) error {
 		}
 		addresses = append(addresses, address.String())
 	}
-	if _, ok := m.genHeader[HeaderDispositionNotificationTo]; ok {
-		m.genHeader[HeaderDispositionNotificationTo] = addresses
-	}
+	m.genHeader[HeaderDispositionNotificationTo] = addresses
 	return nil
 }
 
@@ -1249,11 +1308,11 @@ func (m *Msg) RequestMDNAddTo(rcpt string) error {
 		return fmt.Errorf(errParseMailAddr, rcpt, err)
 	}
 	var addresses []string
-	addresses = append(addresses, m.genHeader[HeaderDispositionNotificationTo]...)
-	addresses = append(addresses, address.String())
-	if _, ok := m.genHeader[HeaderDispositionNotificationTo]; ok {
-		m.genHeader[HeaderDispositionNotificationTo] = addresses
+	if current, ok := m.genHeader[HeaderDispositionNotificationTo]; ok {
+		addresses = current
 	}
+	addresses = append(addresses, address.String())
+	m.genHeader[HeaderDispositionNotificationTo] = addresses
 	return nil
 }
 
@@ -1693,11 +1752,11 @@ func (m *Msg) SetBodyHTMLTemplate(tpl *ht.Template, data interface{}, opts ...Pa
 	if tpl == nil {
 		return errors.New(errTplPointerNil)
 	}
-	buffer := bytes.Buffer{}
-	if err := tpl.Execute(&buffer, data); err != nil {
+	buffer := bytes.NewBuffer(nil)
+	if err := tpl.Execute(buffer, data); err != nil {
 		return fmt.Errorf(errTplExecuteFailed, err)
 	}
-	writeFunc := writeFuncFromBuffer(&buffer)
+	writeFunc := writeFuncFromBuffer(buffer)
 	m.SetBodyWriter(TypeTextHTML, writeFunc, opts...)
 	return nil
 }
@@ -1724,11 +1783,11 @@ func (m *Msg) SetBodyTextTemplate(tpl *tt.Template, data interface{}, opts ...Pa
 	if tpl == nil {
 		return errors.New(errTplPointerNil)
 	}
-	buf := bytes.Buffer{}
-	if err := tpl.Execute(&buf, data); err != nil {
+	buffer := bytes.NewBuffer(nil)
+	if err := tpl.Execute(buffer, data); err != nil {
 		return fmt.Errorf(errTplExecuteFailed, err)
 	}
-	writeFunc := writeFuncFromBuffer(&buf)
+	writeFunc := writeFuncFromBuffer(buffer)
 	m.SetBodyWriter(TypeTextPlain, writeFunc, opts...)
 	return nil
 }
@@ -1798,11 +1857,11 @@ func (m *Msg) AddAlternativeHTMLTemplate(tpl *ht.Template, data interface{}, opt
 	if tpl == nil {
 		return errors.New(errTplPointerNil)
 	}
-	buffer := bytes.Buffer{}
-	if err := tpl.Execute(&buffer, data); err != nil {
+	buffer := bytes.NewBuffer(nil)
+	if err := tpl.Execute(buffer, data); err != nil {
 		return fmt.Errorf(errTplExecuteFailed, err)
 	}
-	writeFunc := writeFuncFromBuffer(&buffer)
+	writeFunc := writeFuncFromBuffer(buffer)
 	m.AddAlternativeWriter(TypeTextHTML, writeFunc, opts...)
 	return nil
 }
@@ -1828,11 +1887,11 @@ func (m *Msg) AddAlternativeTextTemplate(tpl *tt.Template, data interface{}, opt
 	if tpl == nil {
 		return errors.New(errTplPointerNil)
 	}
-	buffer := bytes.Buffer{}
-	if err := tpl.Execute(&buffer, data); err != nil {
+	buffer := bytes.NewBuffer(nil)
+	if err := tpl.Execute(buffer, data); err != nil {
 		return fmt.Errorf(errTplExecuteFailed, err)
 	}
-	writeFunc := writeFuncFromBuffer(&buffer)
+	writeFunc := writeFuncFromBuffer(buffer)
 	m.AddAlternativeWriter(TypeTextPlain, writeFunc, opts...)
 	return nil
 }
@@ -2429,8 +2488,8 @@ func (m *Msg) WriteToSendmailWithContext(ctx context.Context, sendmailPath strin
 //   - https://datatracker.ietf.org/doc/html/rfc5322
 func (m *Msg) NewReader() *Reader {
 	reader := &Reader{}
-	buffer := bytes.Buffer{}
-	_, err := m.Write(&buffer)
+	buffer := bytes.NewBuffer(nil)
+	_, err := m.Write(buffer)
 	if err != nil {
 		reader.err = fmt.Errorf("failed to write Msg to Reader buffer: %w", err)
 	}

msg_nowin_test.go

@@ -1,85 +0,0 @@
-// SPDX-FileCopyrightText: 2022-2023 The go-mail Authors
-//
-// SPDX-License-Identifier: MIT
-
-//go:build !windows
-// +build !windows
-
-package mail
-
-import (
-	"context"
-	"os"
-	"testing"
-	"time"
-)
-
-// TestMsg_WriteToSendmailWithContext tests the WriteToSendmailWithContext() method of the Msg
-func TestMsg_WriteToSendmailWithContext(t *testing.T) {
-	if os.Getenv("TEST_SKIP_SENDMAIL") != "" {
-		t.Skipf("TEST_SKIP_SENDMAIL variable is set. Skipping sendmail test")
-	}
-	tests := []struct {
-		name string
-		sp   string
-		sf   bool
-	}{
-		{"Sendmail path: /dev/null", "/dev/null", true},
-		{"Sendmail path: /bin/cat", "/bin/cat", true},
-		{"Sendmail path: /is/invalid", "/is/invalid", true},
-		{"Sendmail path: /bin/echo", "/bin/echo", false},
-	}
-	m := NewMsg()
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			ctx, cfn := context.WithTimeout(context.Background(), time.Second*10)
-			defer cfn()
-			m.SetBodyString(TypeTextPlain, "Plain")
-			if err := m.WriteToSendmailWithContext(ctx, tt.sp); err != nil && !tt.sf {
-				t.Errorf("WriteToSendmailWithCommand() failed: %s", err)
-			}
-			m.Reset()
-		})
-	}
-}
-
-// TestMsg_WriteToSendmail will test the output to the local sendmail command
-func TestMsg_WriteToSendmail(t *testing.T) {
-	if os.Getenv("TEST_SKIP_SENDMAIL") != "" {
-		t.Skipf("TEST_SKIP_SENDMAIL variable is set. Skipping sendmail test")
-	}
-	_, err := os.Stat(SendmailPath)
-	if err != nil {
-		t.Skipf("local sendmail command not found in expected path. Skipping")
-	}
-
-	m := NewMsg()
-	_ = m.From("Toni Tester <tester@example.com>")
-	_ = m.To(TestRcpt)
-	m.SetBodyString(TypeTextPlain, "This is a test")
-	if err := m.WriteToSendmail(); err != nil {
-		t.Errorf("WriteToSendmail failed: %s", err)
-	}
-}
-
-func TestMsg_WriteToTempFileFailed(t *testing.T) {
-	m := NewMsg()
-	_ = m.From("Toni Tester <tester@example.com>")
-	_ = m.To("Ellenor Tester <ellinor@example.com>")
-	m.SetBodyString(TypeTextPlain, "This is a test")
-
-	curTmpDir := os.Getenv("TMPDIR")
-	defer func() {
-		if err := os.Setenv("TMPDIR", curTmpDir); err != nil {
-			t.Errorf("failed to set TMPDIR environment variable: %s", err)
-		}
-	}()
-
-	if err := os.Setenv("TMPDIR", "/invalid/directory/that/does/not/exist"); err != nil {
-		t.Errorf("failed to set TMPDIR environment variable: %s", err)
-	}
-	_, err := m.WriteToTempFile()
-	if err == nil {
-		t.Errorf("WriteToTempFile() did not fail as expected")
-	}
-}

msg_unix_test.go

@@ -0,0 +1,146 @@
+// SPDX-FileCopyrightText: 2022-2023 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT
+
+//go:build linux || freebsd
+// +build linux freebsd
+
+package mail
+
+import (
+	"bytes"
+	"errors"
+	"os"
+	"testing"
+)
+
+func TestMsg_AttachFile_unixOnly(t *testing.T) {
+	t.Run("AttachFile with fileFromFS fails on open", func(t *testing.T) {
+		if os.Getenv("PERFORM_UNIX_OPEN_WRITE_TESTS") != "true" {
+			t.Skipf("PERFORM_UNIX_OPEN_WRITE_TESTS variable is not set. Skipping unix open/write tests")
+		}
+
+		tempFile, err := os.CreateTemp("", "attachfile-open-write-test.*.txt")
+		if err != nil {
+			t.Fatalf("failed to create temp file: %s", err)
+		}
+		t.Cleanup(func() {
+			if err := os.Remove(tempFile.Name()); err != nil {
+				t.Errorf("failed to remove temp file: %s", err)
+			}
+		})
+		if err = os.Chmod(tempFile.Name(), 0o000); err != nil {
+			t.Fatalf("failed to chmod temp file: %s", err)
+		}
+
+		message := NewMsg()
+		if message == nil {
+			t.Fatal("message is nil")
+		}
+		message.AttachFile(tempFile.Name())
+		attachments := message.GetAttachments()
+		if len(attachments) != 1 {
+			t.Fatalf("failed to get attachments, expected 1, got: %d", len(attachments))
+		}
+		messageBuf := bytes.NewBuffer(nil)
+		_, err = attachments[0].Writer(messageBuf)
+		if err == nil {
+			t.Error("writer func expected to fail, but didn't")
+		}
+		if !errors.Is(err, os.ErrPermission) {
+			t.Errorf("expected error to be %s, got: %s", os.ErrPermission, err)
+		}
+	})
+}
+
+func TestMsg_EmbedFile_unixOnly(t *testing.T) {
+	t.Run("EmbedFile with fileFromFS fails on open", func(t *testing.T) {
+		if os.Getenv("PERFORM_UNIX_OPEN_WRITE_TESTS") != "true" {
+			t.Skipf("PERFORM_UNIX_OPEN_WRITE_TESTS variable is not set. Skipping unix open/write tests")
+		}
+
+		tempFile, err := os.CreateTemp("", "embedfile-open-write-test.*.txt")
+		if err != nil {
+			t.Fatalf("failed to create temp file: %s", err)
+		}
+		t.Cleanup(func() {
+			if err := os.Remove(tempFile.Name()); err != nil {
+				t.Errorf("failed to remove temp file: %s", err)
+			}
+		})
+		if err = os.Chmod(tempFile.Name(), 0o000); err != nil {
+			t.Fatalf("failed to chmod temp file: %s", err)
+		}
+
+		message := NewMsg()
+		if message == nil {
+			t.Fatal("message is nil")
+		}
+		message.EmbedFile(tempFile.Name())
+		embeds := message.GetEmbeds()
+		if len(embeds) != 1 {
+			t.Fatalf("failed to get embeds, expected 1, got: %d", len(embeds))
+		}
+		messageBuf := bytes.NewBuffer(nil)
+		_, err = embeds[0].Writer(messageBuf)
+		if err == nil {
+			t.Error("writer func expected to fail, but didn't")
+		}
+		if !errors.Is(err, os.ErrPermission) {
+			t.Errorf("expected error to be %s, got: %s", os.ErrPermission, err)
+		}
+	})
+}
+
+func TestMsg_WriteToFile_unixOnly(t *testing.T) {
+	t.Run("WriteToFile fails on create", func(t *testing.T) {
+		if os.Getenv("PERFORM_UNIX_OPEN_WRITE_TESTS") != "true" {
+			t.Skipf("PERFORM_UNIX_OPEN_WRITE_TESTS variable is not set. Skipping unix open/write tests")
+		}
+
+		tempfile, err := os.CreateTemp("", "testmail-create.*.eml")
+		if err != nil {
+			t.Fatalf("failed to create temp file: %s", err)
+		}
+		if err = os.Chmod(tempfile.Name(), 0o000); err != nil {
+			t.Fatalf("failed to chmod temp file: %s", err)
+		}
+		t.Cleanup(func() {
+			if err = tempfile.Close(); err != nil {
+				t.Fatalf("failed to close temp file: %s", err)
+			}
+			if err = os.Remove(tempfile.Name()); err != nil {
+				t.Fatalf("failed to remove temp file: %s", err)
+			}
+		})
+		message := testMessage(t)
+		if err = message.WriteToFile(tempfile.Name()); err == nil {
+			t.Errorf("expected error, got nil")
+		}
+	})
+}
+
+func TestMsg_WriteToTempFile_unixOnly(t *testing.T) {
+	if os.Getenv("PERFORM_UNIX_OPEN_WRITE_TESTS") != "true" {
+		t.Skipf("PERFORM_UNIX_OPEN_WRITE_TESTS variable is not set. Skipping unix open/write tests")
+	}
+
+	t.Run("WriteToTempFile fails on invalid TMPDIR", func(t *testing.T) {
+		// We store the current TMPDIR variable so we can set it back when the test is over
+		curTmpDir := os.Getenv("TMPDIR")
+		t.Cleanup(func() {
+			if err := os.Setenv("TMPDIR", curTmpDir); err != nil {
+				t.Errorf("failed to set TMPDIR environment variable: %s", err)
+			}
+		})
+
+		if err := os.Setenv("TMPDIR", "/invalid/directory/that/does/not/exist"); err != nil {
+			t.Fatalf("failed to set TMPDIR environment variable: %s", err)
+		}
+		message := testMessage(t)
+		_, err := message.WriteToTempFile()
+		if err == nil {
+			t.Errorf("expected writing to invalid TMPDIR to fail, got: %s", err)
+		}
+	})
+}

msgwriter_test.go

@@ -6,153 +6,675 @@ package mail
 
 import (
 	"bytes"
+	"errors"
 	"fmt"
 	"io"
 	"mime"
+	"runtime"
 	"strings"
 	"testing"
 	"time"
 )
 
-// brokenWriter implements a broken writer for io.Writer testing
-type brokenWriter struct {
-	io.Writer
-}
-
-// Write implements the io.Writer interface but intentionally returns an error at
-// any time
-func (bw *brokenWriter) Write([]byte) (int, error) {
-	return 0, fmt.Errorf("intentionally failed")
-}
-
-// TestMsgWriter_Write tests the WriteTo() method of the msgWriter
 func TestMsgWriter_Write(t *testing.T) {
-	bw := &brokenWriter{}
-	mw := &msgWriter{writer: bw, charset: CharsetUTF8, encoder: mime.QEncoding}
-	_, err := mw.Write([]byte("test"))
-	if err == nil {
-		t.Errorf("msgWriter WriteTo() with brokenWriter should fail, but didn't")
-	}
-
-	// Also test the part when a previous error happened
-	mw.err = fmt.Errorf("broken")
-	_, err = mw.Write([]byte("test"))
-	if err == nil {
-		t.Errorf("msgWriter WriteTo() with brokenWriter should fail, but didn't")
-	}
-}
-
-// TestMsgWriter_writeMsg tests the writeMsg method of the msgWriter
-func TestMsgWriter_writeMsg(t *testing.T) {
-	m := NewMsg()
-	_ = m.From(`"Toni Tester" <test@example.com>`)
-	_ = m.To(`"Toni Receiver" <receiver@example.com>`)
-	m.Subject("This is a subject")
-	m.SetBulk()
-	now := time.Now()
-	m.SetDateWithValue(now)
-	m.SetMessageIDWithValue("message@id.com")
-	m.SetBodyString(TypeTextPlain, "This is the body")
-	m.AddAlternativeString(TypeTextHTML, "This is the alternative body")
-	buf := bytes.Buffer{}
-	mw := &msgWriter{writer: &buf, charset: CharsetUTF8, encoder: mime.QEncoding}
-	mw.writeMsg(m)
-	ms := buf.String()
-
-	var ea []string
-	if !strings.Contains(ms, `MIME-Version: 1.0`) {
-		ea = append(ea, "MIME-Version")
-	}
-	if !strings.Contains(ms, fmt.Sprintf("Date: %s", now.Format(time.RFC1123Z))) {
-		ea = append(ea, "Date")
-	}
-	if !strings.Contains(ms, `Message-ID: <message@id.com>`) {
-		ea = append(ea, "Message-ID")
-	}
-	if !strings.Contains(ms, `Precedence: bulk`) {
-		ea = append(ea, "Precedence")
-	}
-	if !strings.Contains(ms, `Subject: This is a subject`) {
-		ea = append(ea, "Subject")
-	}
-	if !strings.Contains(ms, `User-Agent: go-mail v`) {
-		ea = append(ea, "User-Agent")
-	}
-	if !strings.Contains(ms, `X-Mailer: go-mail v`) {
-		ea = append(ea, "X-Mailer")
-	}
-	if !strings.Contains(ms, `From: "Toni Tester" <test@example.com>`) {
-		ea = append(ea, "From")
-	}
-	if !strings.Contains(ms, `To: "Toni Receiver" <receiver@example.com>`) {
-		ea = append(ea, "To")
-	}
-	if !strings.Contains(ms, `Content-Type: text/plain; charset=UTF-8`) {
-		ea = append(ea, "Content-Type")
-	}
-	if !strings.Contains(ms, `Content-Transfer-Encoding: quoted-printable`) {
-		ea = append(ea, "Content-Transfer-Encoding")
-	}
-	if !strings.Contains(ms, "\r\n\r\nThis is the body") {
-		ea = append(ea, "Message body")
-	}
-
-	pl := m.GetParts()
-	if len(pl) <= 0 {
-		t.Errorf("expected multiple parts but got none")
-		return
-	}
-	if len(pl) == 2 {
-		ap := pl[1]
-		ap.SetCharset(CharsetISO88591)
-	}
-	buf.Reset()
-	mw.writeMsg(m)
-	ms = buf.String()
-	if !strings.Contains(ms, "\r\n\r\nThis is the alternative body") {
-		ea = append(ea, "Message alternative body")
-	}
-	if !strings.Contains(ms, `Content-Type: text/html; charset=ISO-8859-1`) {
-		ea = append(ea, "alternative body charset")
-	}
-
-	if len(ea) > 0 {
-		em := "writeMsg() failed. The following errors occurred:\n"
-		for e := range ea {
-			em += fmt.Sprintf("* incorrect %q field", ea[e])
+	t.Run("msgWriter writes to memory for all charsets", func(t *testing.T) {
+		for _, tt := range charsetTests {
+			t.Run(tt.name, func(t *testing.T) {
+				buffer := bytes.NewBuffer(nil)
+				msgwriter := &msgWriter{
+					writer:  buffer,
+					charset: tt.value,
+					encoder: mime.QEncoding,
+				}
+				_, err := msgwriter.Write([]byte("test"))
+				if err != nil {
+					t.Errorf("msgWriter failed to write: %s", err)
+				}
+			})
 		}
-		em += fmt.Sprintf("\n\nFull message:\n%s", ms)
-		t.Error(em)
-	}
+	})
+	t.Run("msgWriter writes to memory for all encodings", func(t *testing.T) {
+		for _, tt := range encodingTests {
+			t.Run(tt.name, func(t *testing.T) {
+				buffer := bytes.NewBuffer(nil)
+				msgwriter := &msgWriter{
+					writer:  buffer,
+					charset: CharsetUTF8,
+					encoder: getEncoder(tt.value),
+				}
+				_, err := msgwriter.Write([]byte("test"))
+				if err != nil {
+					t.Errorf("msgWriter failed to write: %s", err)
+				}
+			})
+		}
+	})
+	t.Run("msgWriter should fail on write", func(t *testing.T) {
+		msgwriter := &msgWriter{
+			writer:  failReadWriteSeekCloser{},
+			charset: CharsetUTF8,
+			encoder: getEncoder(EncodingQP),
+		}
+		_, err := msgwriter.Write([]byte("test"))
+		if err == nil {
+			t.Fatalf("msgWriter was supposed to fail on write")
+		}
+	})
+	t.Run("msgWriter should fail on previous error", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter := &msgWriter{
+			writer:  buffer,
+			charset: CharsetUTF8,
+			encoder: getEncoder(EncodingQP),
+		}
+		_, err := msgwriter.Write([]byte("test"))
+		if err != nil {
+			t.Errorf("msgWriter failed to write: %s", err)
+		}
+		msgwriter.err = errors.New("intentionally failed")
+		_, err = msgwriter.Write([]byte("test2"))
+		if err == nil {
+			t.Fatalf("msgWriter was supposed to fail on second write")
+		}
+	})
 }
 
-// TestMsgWriter_writeMsg_PGP tests the writeMsg method of the msgWriter with PGP types set
-func TestMsgWriter_writeMsg_PGP(t *testing.T) {
-	m := NewMsg(WithPGPType(PGPEncrypt))
-	_ = m.From(`"Toni Tester" <test@example.com>`)
-	_ = m.To(`"Toni Receiver" <receiver@example.com>`)
-	m.Subject("This is a subject")
-	m.SetBodyString(TypeTextPlain, "This is the body")
-	buf := bytes.Buffer{}
-	mw := &msgWriter{writer: &buf, charset: CharsetUTF8, encoder: mime.QEncoding}
-	mw.writeMsg(m)
-	ms := buf.String()
-	if !strings.Contains(ms, `encrypted; protocol="application/pgp-encrypted"`) {
-		t.Errorf("writeMsg failed. Expected PGP encoding header but didn't find it in message output")
+func TestMsgWriter_writeMsg(t *testing.T) {
+	msgwriter := &msgWriter{
+		charset: CharsetUTF8,
+		encoder: getEncoder(EncodingQP),
 	}
+	t.Run("msgWriter writes a simple message", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		now := time.Now()
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.SetDateWithValue(now)
+		message.SetMessageIDWithValue("message@id.com")
+		message.SetBulk()
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
 
-	m = NewMsg(WithPGPType(PGPSignature))
-	_ = m.From(`"Toni Tester" <test@example.com>`)
-	_ = m.To(`"Toni Receiver" <receiver@example.com>`)
-	m.Subject("This is a subject")
-	m.SetBodyString(TypeTextPlain, "This is the body")
-	buf = bytes.Buffer{}
-	mw = &msgWriter{writer: &buf, charset: CharsetUTF8, encoder: mime.QEncoding}
-	mw.writeMsg(m)
-	ms = buf.String()
-	if !strings.Contains(ms, `signed; protocol="application/pgp-signature"`) {
-		t.Errorf("writeMsg failed. Expected PGP encoding header but didn't find it in message output")
+		var incorrectFields []string
+		if !strings.Contains(buffer.String(), "MIME-Version: 1.0\r\n") {
+			incorrectFields = append(incorrectFields, "MIME-Version")
+		}
+		if !strings.Contains(buffer.String(), fmt.Sprintf("Date: %s\r\n", now.Format(time.RFC1123Z))) {
+			incorrectFields = append(incorrectFields, "Date")
+		}
+		if !strings.Contains(buffer.String(), "Message-ID: <message@id.com>\r\n") {
+			incorrectFields = append(incorrectFields, "Message-ID")
+		}
+		if !strings.Contains(buffer.String(), "Precedence: bulk\r\n") {
+			incorrectFields = append(incorrectFields, "Precedence")
+		}
+		if !strings.Contains(buffer.String(), "X-Auto-Response-Suppress: All\r\n") {
+			incorrectFields = append(incorrectFields, "X-Auto-Response-Suppress")
+		}
+		if !strings.Contains(buffer.String(), "Subject: Testmail\r\n") {
+			incorrectFields = append(incorrectFields, "Subject")
+		}
+		if !strings.Contains(buffer.String(), "User-Agent: go-mail v") {
+			incorrectFields = append(incorrectFields, "User-Agent")
+		}
+		if !strings.Contains(buffer.String(), "X-Mailer: go-mail v") {
+			incorrectFields = append(incorrectFields, "X-Mailer")
+		}
+		if !strings.Contains(buffer.String(), `From: <`+TestSenderValid+`>`) {
+			incorrectFields = append(incorrectFields, "From")
+		}
+		if !strings.Contains(buffer.String(), `To: <`+TestRcptValid+`>`) {
+			incorrectFields = append(incorrectFields, "From")
+		}
+		if !strings.Contains(buffer.String(), "Content-Type: text/plain; charset=UTF-8\r\n") {
+			incorrectFields = append(incorrectFields, "Content-Type")
+		}
+		if !strings.Contains(buffer.String(), "Content-Transfer-Encoding: quoted-printable\r\n") {
+			incorrectFields = append(incorrectFields, "Content-Transfer-Encoding")
+		}
+		if !strings.HasSuffix(buffer.String(), "\r\n\r\nTestmail") {
+			incorrectFields = append(incorrectFields, "Message body")
+		}
+		if len(incorrectFields) > 0 {
+			t.Fatalf("msgWriter failed to write correct fields: %s - mail: %s",
+				strings.Join(incorrectFields, ", "), buffer.String())
+		}
+	})
+	t.Run("msgWriter with no from address uses envelope from", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := NewMsg()
+		if message == nil {
+			t.Fatal("failed to create new message")
+		}
+		if err := message.EnvelopeFrom(TestSenderValid); err != nil {
+			t.Errorf("failed to set sender address: %s", err)
+		}
+		if err := message.To(TestRcptValid); err != nil {
+			t.Errorf("failed to set recipient address: %s", err)
+		}
+		message.Subject("Testmail")
+		message.SetBodyString(TypeTextPlain, "Testmail")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "From: <"+TestSenderValid+">") {
+			t.Errorf("expected envelope from address as from address, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter with no from address or envelope from", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := NewMsg()
+		if message == nil {
+			t.Fatal("failed to create new message")
+		}
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if strings.Contains(buffer.String(), "From:") {
+			t.Errorf("expected no from address, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter writes a multipart/mixed message", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithBoundary("testboundary"))
+		message.AttachFile("testdata/attachment.txt")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "Content-Type: multipart/mixed") {
+			t.Errorf("expected multipart/mixed, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary\r\n") {
+			t.Errorf("expected boundary, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary--") {
+			t.Errorf("expected end boundary, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter writes a multipart/related message", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithBoundary("testboundary"))
+		message.EmbedFile("testdata/embed.txt")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "Content-Type: multipart/related") {
+			t.Errorf("expected multipart/related, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary\r\n") {
+			t.Errorf("expected boundary, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary--") {
+			t.Errorf("expected end boundary, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter writes a multipart/alternative message", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithBoundary("testboundary"))
+		message.AddAlternativeString(TypeTextHTML, "<html><body><h1>Testmail</h1></body></html>")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "Content-Type: multipart/alternative") {
+			t.Errorf("expected multipart/alternative, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary\r\n") {
+			t.Errorf("expected boundary, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary--") {
+			t.Errorf("expected end boundary, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter writes a application/pgp-encrypted message", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithPGPType(PGPEncrypt), WithBoundary("testboundary"))
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "Content-Type: multipart/encrypted") {
+			t.Errorf("expected multipart/encrypted, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary\r\n") {
+			t.Errorf("expected boundary, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter writes a application/pgp-signature message", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithPGPType(PGPSignature), WithBoundary("testboundary"))
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "Content-Type: multipart/signed") {
+			t.Errorf("expected multipart/signed, got: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "--testboundary\r\n") {
+			t.Errorf("expected boundary, got: %s", buffer.String())
+		}
+	})
+	t.Run("msgWriter should ignore NoPGP", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithBoundary("testboundary"))
+		message.pgptype = 9
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "--testboundary\r\n") {
+			t.Errorf("expected boundary, got: %s", buffer.String())
+		}
+	})
+}
+
+func TestMsgWriter_writePreformattedGenHeader(t *testing.T) {
+	t.Run("message with no preformatted headerset", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter := &msgWriter{
+			writer:  buffer,
+			charset: CharsetUTF8,
+			encoder: getEncoder(EncodingQP),
+		}
+		message := testMessage(t)
+		message.SetGenHeaderPreformatted(HeaderContentID, "This is a content id")
+		msgwriter.writeMsg(message)
+		if !strings.Contains(buffer.String(), "Content-ID: This is a content id\r\n") {
+			t.Errorf("expected preformatted header, got: %s", buffer.String())
+		}
+	})
+}
+
+func TestMsgWriter_addFiles(t *testing.T) {
+	msgwriter := &msgWriter{
+		charset: CharsetUTF8,
+		encoder: getEncoder(EncodingQP),
 	}
+	t.Run("message with a single file attached", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.AttachFile("testdata/attachment.txt")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		switch runtime.GOOS {
+		case "windows":
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudA0K") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudAo=") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Disposition: attachment; filename="attachment.txt"`) {
+			t.Errorf("Content-Dispositon header not found for attachment. Mail: %s", buffer.String())
+		}
+		switch runtime.GOOS {
+		case "freebsd":
+			if !strings.Contains(buffer.String(), `Content-Type: application/octet-stream; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), `Content-Type: text/plain; charset=utf-8; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		}
+	})
+	t.Run("message with a single file attached no extension", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.AttachFile("testdata/attachment")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		switch runtime.GOOS {
+		case "windows":
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudA0K") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudAo=") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Disposition: attachment; filename="attachment"`) {
+			t.Errorf("Content-Dispositon header not found for attachment. Mail: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), `Content-Type: application/octet-stream; name="attachment"`) {
+			t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+		}
+	})
+	t.Run("message with a single file attached custom content-type", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.AttachFile("testdata/attachment.txt", WithFileContentType(TypeAppOctetStream))
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		switch runtime.GOOS {
+		case "windows":
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudA0K") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudAo=") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Disposition: attachment; filename="attachment.txt"`) {
+			t.Errorf("Content-Dispositon header not found for attachment. Mail: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), `Content-Type: application/octet-stream; name="attachment.txt"`) {
+			t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+		}
+	})
+	t.Run("message with a single file attached custom transfer-encoding", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.AttachFile("testdata/attachment.txt", WithFileEncoding(EncodingUSASCII))
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "\r\n\r\nThis is a test attachment") {
+			t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), `Content-Disposition: attachment; filename="attachment.txt"`) {
+			t.Errorf("Content-Dispositon header not found for attachment. Mail: %s", buffer.String())
+		}
+		switch runtime.GOOS {
+		case "freebsd":
+			if !strings.Contains(buffer.String(), `Content-Type: application/octet-stream; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), `Content-Type: text/plain; charset=utf-8; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Transfer-Encoding: 7bit`) {
+			t.Errorf("Content-Transfer-Encoding header not found for attachment. Mail: %s", buffer.String())
+		}
+	})
+	t.Run("message with a single file attached custom description", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.AttachFile("testdata/attachment.txt", WithFileDescription("Testdescription"))
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		switch runtime.GOOS {
+		case "windows":
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudA0K") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudAo=") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Disposition: attachment; filename="attachment.txt"`) {
+			t.Errorf("Content-Dispositon header not found for attachment. Mail: %s", buffer.String())
+		}
+		switch runtime.GOOS {
+		case "freebsd":
+			if !strings.Contains(buffer.String(), `Content-Type: application/octet-stream; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), `Content-Type: text/plain; charset=utf-8; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Transfer-Encoding: base64`) {
+			t.Errorf("Content-Transfer-Encoding header not found for attachment. Mail: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), `Content-Description: Testdescription`) {
+			t.Errorf("Content-Description header not found for attachment. Mail: %s", buffer.String())
+		}
+	})
+	t.Run("message with attachment but no body part", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.parts = nil
+		message.AttachFile("testdata/attachment.txt")
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		switch runtime.GOOS {
+		case "windows":
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudA0K") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), "VGhpcyBpcyBhIHRlc3QgYXR0YWNobWVudAo=") {
+				t.Errorf("attachment not found in mail message. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Disposition: attachment; filename="attachment.txt"`) {
+			t.Errorf("Content-Dispositon header not found for attachment. Mail: %s", buffer.String())
+		}
+		switch runtime.GOOS {
+		case "freebsd":
+			if !strings.Contains(buffer.String(), `Content-Type: application/octet-stream; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		default:
+			if !strings.Contains(buffer.String(), `Content-Type: text/plain; charset=utf-8; name="attachment.txt"`) {
+				t.Errorf("Content-Type header not found for attachment. Mail: %s", buffer.String())
+			}
+		}
+		if !strings.Contains(buffer.String(), `Content-Transfer-Encoding: base64`) {
+			t.Errorf("Content-Transfer-Encoding header not found for attachment. Mail: %s", buffer.String())
+		}
+	})
+}
+
+func TestMsgWriter_writePart(t *testing.T) {
+	msgwriter := &msgWriter{
+		charset: CharsetUTF8,
+		encoder: getEncoder(EncodingQP),
+	}
+	t.Run("message with no part charset should use default message charset", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t, WithCharset(CharsetUTF7))
+		message.AddAlternativeString(TypeTextPlain, "thisisatest")
+		message.parts[1].charset = ""
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "ontent-Type: text/plain; charset=UTF-7\r\n\r\nTestmail") {
+			t.Errorf("part not found in mail message. Mail: %s", buffer.String())
+		}
+		if !strings.Contains(buffer.String(), "ontent-Type: text/plain; charset=UTF-7\r\n\r\nthisisatest") {
+			t.Errorf("part not found in mail message. Mail: %s", buffer.String())
+		}
+	})
+	t.Run("message with parts that have a description", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		message.AddAlternativeString(TypeTextPlain, "thisisatest")
+		message.parts[1].description = "thisisadescription"
+		msgwriter.writeMsg(message)
+		if msgwriter.err != nil {
+			t.Errorf("msgWriter failed to write: %s", msgwriter.err)
+		}
+		if !strings.Contains(buffer.String(), "Content-Description: thisisadescription") {
+			t.Errorf("part description not found in mail message. Mail: %s", buffer.String())
+		}
+	})
+}
+
+func TestMsgWriter_writeString(t *testing.T) {
+	msgwriter := &msgWriter{
+		charset: CharsetUTF8,
+		encoder: getEncoder(EncodingQP),
+	}
+	t.Run("writeString succeeds", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		msgwriter.writeString("thisisatest")
+		if !strings.EqualFold(buffer.String(), "thisisatest") {
+			t.Errorf("writeString failed, expected: thisisatest got: %s", buffer.String())
+		}
+	})
+	t.Run("writeString fails", func(t *testing.T) {
+		msgwriter.writer = failReadWriteSeekCloser{}
+		msgwriter.writeString("thisisatest")
+		if msgwriter.err == nil {
+			t.Errorf("writeString succeeded, expected error")
+		}
+	})
+	t.Run("writeString on errored writer should return", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		msgwriter.err = errors.New("intentional error")
+		msgwriter.writeString("thisisatest")
+		if !strings.EqualFold(buffer.String(), "") {
+			t.Errorf("writeString succeeded, expected: empty string, got: %s", buffer.String())
+		}
+	})
+}
+
+func TestMsgWriter_writeHeader(t *testing.T) {
+	msgwriter := &msgWriter{
+		charset: CharsetUTF8,
+		encoder: getEncoder(EncodingQP),
+	}
+	t.Run("writeHeader with single value", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		msgwriter.writeHeader(HeaderMessageID, "this.is.a.test")
+		if !strings.EqualFold(buffer.String(), "Message-ID: this.is.a.test\r\n") {
+			t.Errorf("writeHeader failed, expected: %s, got: %s", "Message-ID: this.is.a.test",
+				buffer.String())
+		}
+	})
+	t.Run("writeHeader with multiple values", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		msgwriter.writeHeader(HeaderMessageID, "this.is.a.test", "this.as.well")
+		if !strings.EqualFold(buffer.String(), "Message-ID: this.is.a.test, this.as.well\r\n") {
+			t.Errorf("writeHeader failed, expected: %s, got: %s", "Message-ID: this.is.a.test, this.as.well",
+				buffer.String())
+		}
+	})
+	t.Run("writeHeader with no values", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		msgwriter.writeHeader(HeaderMessageID)
+		// While technically it is permitted to have empty headers, it's recommend to omit them if
+		// no value is present. We follow this recommendation.
+		if !strings.EqualFold(buffer.String(), "") {
+			t.Errorf("writeHeader failed, expected: %s, got: %s", "", buffer.String())
+		}
+	})
+	t.Run("writeHeader with very long value", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		msgwriter.writeHeader(HeaderMessageID, strings.Repeat("a", MaxHeaderLength-13), "next-row")
+		want := "Message-ID:\r\n " + strings.Repeat("a", MaxHeaderLength-13) + ",\r\n next-row\r\n"
+		if !strings.EqualFold(buffer.String(), want) {
+			t.Errorf("writeHeader failed, expected: %s, got: %s", want, buffer.String())
+		}
+	})
+}
+
+func TestMsgWriter_writeBody(t *testing.T) {
+	t.Log("We only cover some edge-cases here, most of the functionality is tested already very thoroughly.")
+
+	msgwriter := &msgWriter{
+		charset: CharsetUTF8,
+		encoder: getEncoder(EncodingQP),
+	}
+	t.Run("writeBody on NoEncoding", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		message := testMessage(t)
+		msgwriter.writeBody(message.parts[0].writeFunc, NoEncoding, false)
+		if msgwriter.err != nil {
+			t.Errorf("writeBody failed to write: %s", msgwriter.err)
+		}
+	})
+	t.Run("writeBody on NoEncoding fails on write", func(t *testing.T) {
+		msgwriter.writer = failReadWriteSeekCloser{}
+		message := testMessage(t)
+		msgwriter.writeBody(message.parts[0].writeFunc, NoEncoding, false)
+		if msgwriter.err == nil {
+			t.Errorf("writeBody succeeded, expected error")
+		}
+		if !strings.EqualFold(msgwriter.err.Error(), "bodyWriter io.Copy: intentional write failure") {
+			t.Errorf("expected error: bodyWriter io.Copy: intentional write failure, got: %s", msgwriter.err)
+		}
+	})
+	t.Run("writeBody on NoEncoding fails on writeFunc", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		writeFunc := func(io.Writer) (int64, error) {
+			return 0, errors.New("intentional write failure")
+		}
+		msgwriter.writeBody(writeFunc, NoEncoding, false)
+		if msgwriter.err == nil {
+			t.Errorf("writeBody succeeded, expected error")
+		}
+		if !strings.EqualFold(msgwriter.err.Error(), "bodyWriter function: intentional write failure") {
+			t.Errorf("expected error: bodyWriter function: intentional write failure, got: %s", msgwriter.err)
+		}
+	})
+	t.Run("writeBody Quoted-Printable fails on write", func(t *testing.T) {
+		msgwriter.writer = failReadWriteSeekCloser{}
+		message := testMessage(t)
+		msgwriter.writeBody(message.parts[0].writeFunc, EncodingQP, false)
+		if msgwriter.err == nil {
+			t.Errorf("writeBody succeeded, expected error")
+		}
+		if !strings.EqualFold(msgwriter.err.Error(), "bodyWriter function: intentional write failure") {
+			t.Errorf("expected error: bodyWriter function: intentional write failure, got: %s", msgwriter.err)
+		}
+	})
+	t.Run("writeBody Quoted-Printable fails on writeFunc", func(t *testing.T) {
+		buffer := bytes.NewBuffer(nil)
+		msgwriter.writer = buffer
+		writeFunc := func(io.Writer) (int64, error) {
+			return 0, errors.New("intentional write failure")
+		}
+		msgwriter.writeBody(writeFunc, EncodingQP, false)
+		if msgwriter.err == nil {
+			t.Errorf("writeBody succeeded, expected error")
+		}
+		if !strings.EqualFold(msgwriter.err.Error(), "bodyWriter function: intentional write failure") {
+			t.Errorf("expected error: bodyWriter function: intentional write failure, got: %s", msgwriter.err)
+		}
+	})
 }
 
 // TestMsgWriter_writeMsg_SMime tests the writeMsg method of the msgWriter with S/MIME types set

smtp/auth_login.go

@@ -10,9 +10,10 @@ import (
 
 // loginAuth is the type that satisfies the Auth interface for the "SMTP LOGIN" auth
 type loginAuth struct {
-	username, password string
-	host               string
-	respStep           uint8
+	username, password   string
+	host                 string
+	respStep             uint8
+	allowUnencryptedAuth bool
 }
 
 // LoginAuth returns an [Auth] that implements the LOGIN authentication
@@ -29,14 +30,14 @@ type loginAuth struct {
 // See: https://datatracker.ietf.org/doc/html/draft-murchison-sasl-login-00
 // Since there is no official standard RFC and we've seen different implementations
 // of this mechanism (sending "Username:", "Username", "username", "User name", etc.)
-// we follow the IETF-Draft and ignore any server challange to allow compatiblity
+// we follow the IETF-Draft and ignore any server challenge to allow compatibility
 // with most mail servers/providers.
 //
 // LoginAuth will only send the credentials if the connection is using TLS
 // or is connected to localhost. Otherwise authentication will fail with an
 // error, without sending the credentials.
-func LoginAuth(username, password, host string) Auth {
-	return &loginAuth{username, password, host, 0}
+func LoginAuth(username, password, host string, allowUnEnc bool) Auth {
+	return &loginAuth{username, password, host, 0, allowUnEnc}
 }
 
 // Start begins the SMTP authentication process by validating server's TLS status and hostname.
@@ -47,7 +48,7 @@ func (a *loginAuth) Start(server *ServerInfo) (string, []byte, error) {
 	// In particular, it doesn't matter if the server advertises LOGIN auth.
 	// That might just be the attacker saying
 	// "it's ok, you can trust me with your password."
-	if !server.TLS && !isLocalhost(server.Name) {
+	if !a.allowUnencryptedAuth && !server.TLS && !isLocalhost(server.Name) {
 		return "", nil, ErrUnencrypted
 	}
 	if server.Name != a.host {

smtp/auth_plain.go

@@ -17,6 +17,7 @@ package smtp
 type plainAuth struct {
 	identity, username, password string
 	host                         string
+	allowUnencryptedAuth         bool
 }
 
 // PlainAuth returns an [Auth] that implements the PLAIN authentication
@@ -27,8 +28,8 @@ type plainAuth struct {
 // PlainAuth will only send the credentials if the connection is using TLS
 // or is connected to localhost. Otherwise authentication will fail with an
 // error, without sending the credentials.
-func PlainAuth(identity, username, password, host string) Auth {
-	return &plainAuth{identity, username, password, host}
+func PlainAuth(identity, username, password, host string, allowUnEnc bool) Auth {
+	return &plainAuth{identity, username, password, host, allowUnEnc}
 }
 
 func (a *plainAuth) Start(server *ServerInfo) (string, []byte, error) {
@@ -37,7 +38,7 @@ func (a *plainAuth) Start(server *ServerInfo) (string, []byte, error) {
 	// In particular, it doesn't matter if the server advertises PLAIN auth.
 	// That might just be the attacker saying
 	// "it's ok, you can trust me with your password."
-	if !server.TLS && !isLocalhost(server.Name) {
+	if !a.allowUnencryptedAuth && !server.TLS && !isLocalhost(server.Name) {
 		return "", nil, ErrUnencrypted
 	}
 	if server.Name != a.host {

smtp/example_test.go

@@ -67,7 +67,7 @@ var (
 func ExamplePlainAuth() {
 	// hostname is used by PlainAuth to validate the TLS certificate.
 	hostname := "mail.example.com"
-	auth := smtp.PlainAuth("", "user@example.com", "password", hostname)
+	auth := smtp.PlainAuth("", "user@example.com", "password", hostname, false)
 
 	err := smtp.SendMail(hostname+":25", auth, from, recipients, msg)
 	if err != nil {
@@ -77,7 +77,7 @@ func ExamplePlainAuth() {
 
 func ExampleSendMail() {
 	// Set up authentication information.
-	auth := smtp.PlainAuth("", "user@example.com", "password", "mail.example.com")
+	auth := smtp.PlainAuth("", "user@example.com", "password", "mail.example.com", false)
 
 	// Connect to the server, authenticate, set the sender and recipient,
 	// and send the email all in one step.

smtp/smtp.go

@@ -54,6 +54,9 @@ type Client struct {
 	// auth supported auth mechanisms
 	auth []string
 
+	// authIsActive indicates that the Client is currently during SMTP authentication
+	authIsActive bool
+
 	// keep a reference to the connection so it can be used to create a TLS connection later
 	conn net.Conn
 
@@ -78,6 +81,9 @@ type Client struct {
 	// isConnected indicates if the Client has an active connection
 	isConnected bool
 
+	// logAuthData indicates if the Client should include SMTP authentication data in the logs
+	logAuthData bool
+
 	// localName is the name to use in HELO/EHLO
 	localName string // the name to use in HELO/EHLO
 
@@ -174,7 +180,15 @@ func (c *Client) Hello(localName string) error {
 func (c *Client) cmd(expectCode int, format string, args ...interface{}) (int, string, error) {
 	c.mutex.Lock()
 
-	c.debugLog(log.DirClientToServer, format, args...)
+	var logMsg []interface{}
+	logMsg = args
+	logFmt := format
+	if c.authIsActive {
+		logMsg = []interface{}{"<SMTP auth data redacted>"}
+		logFmt = "%s"
+	}
+	c.debugLog(log.DirClientToServer, logFmt, logMsg...)
+
 	id, err := c.Text.Cmd(format, args...)
 	if err != nil {
 		c.mutex.Unlock()
@@ -182,7 +196,13 @@ func (c *Client) cmd(expectCode int, format string, args ...interface{}) (int, s
 	}
 	c.Text.StartResponse(id)
 	code, msg, err := c.Text.ReadResponse(expectCode)
-	c.debugLog(log.DirServerToClient, "%d %s", code, msg)
+
+	logMsg = []interface{}{code, msg}
+	if c.authIsActive && code >= 300 && code <= 400 {
+		logMsg = []interface{}{code, "<SMTP auth data redacted>"}
+	}
+	c.debugLog(log.DirServerToClient, "%d %s", logMsg...)
+
 	c.Text.EndResponse(id)
 	c.mutex.Unlock()
 	return code, msg, err
@@ -256,6 +276,20 @@ func (c *Client) Auth(a Auth) error {
 	if err := c.hello(); err != nil {
 		return err
 	}
+
+	c.mutex.Lock()
+	if !c.logAuthData {
+		c.authIsActive = true
+	}
+	c.mutex.Unlock()
+	defer func() {
+		c.mutex.Lock()
+		if !c.logAuthData {
+			c.authIsActive = false
+		}
+		c.mutex.Unlock()
+	}()
+
 	encoding := base64.StdEncoding
 	mech, resp, err := a.Start(&ServerInfo{c.serverName, c.tls, c.auth})
 	if err != nil {
@@ -520,9 +554,9 @@ func (c *Client) Noop() error {
 
 // Quit sends the QUIT command and closes the connection to the server.
 func (c *Client) Quit() error {
-	if err := c.hello(); err != nil {
-		return err
-	}
+	// See https://github.com/golang/go/issues/70011
+	_ = c.hello() // ignore error; we're quitting anyhow
+
 	_, _, err := c.cmd(221, "QUIT")
 	if err != nil {
 		return err
@@ -556,6 +590,13 @@ func (c *Client) SetLogger(l log.Logger) {
 	c.logger = l
 }
 
+// SetLogAuthData enables logging of authentication data in the Client.
+func (c *Client) SetLogAuthData() {
+	c.mutex.Lock()
+	c.logAuthData = true
+	c.mutex.Unlock()
+}
+
 // SetDSNMailReturnOption sets the DSN mail return option for the Mail method
 func (c *Client) SetDSNMailReturnOption(d string) {
 	c.dsnmrtype = d

smtp/smtp_test.go

@@ -50,7 +50,7 @@ type authTest struct {
 
 var authTests = []authTest{
 	{
-		PlainAuth("", "user", "pass", "testserver"),
+		PlainAuth("", "user", "pass", "testserver", false),
 		[]string{},
 		"PLAIN",
 		[]string{"\x00user\x00pass"},
@@ -58,7 +58,15 @@ var authTests = []authTest{
 		false,
 	},
 	{
-		PlainAuth("foo", "bar", "baz", "testserver"),
+		PlainAuth("", "user", "pass", "testserver", true),
+		[]string{},
+		"PLAIN",
+		[]string{"\x00user\x00pass"},
+		[]bool{false, false},
+		false,
+	},
+	{
+		PlainAuth("foo", "bar", "baz", "testserver", false),
 		[]string{},
 		"PLAIN",
 		[]string{"foo\x00bar\x00baz"},
@@ -66,7 +74,7 @@ var authTests = []authTest{
 		false,
 	},
 	{
-		PlainAuth("foo", "bar", "baz", "testserver"),
+		PlainAuth("foo", "bar", "baz", "testserver", false),
 		[]string{"foo"},
 		"PLAIN",
 		[]string{"foo\x00bar\x00baz", ""},
@@ -74,7 +82,7 @@ var authTests = []authTest{
 		false,
 	},
 	{
-		LoginAuth("user", "pass", "testserver"),
+		LoginAuth("user", "pass", "testserver", false),
 		[]string{"Username:", "Password:"},
 		"LOGIN",
 		[]string{"", "user", "pass"},
@@ -82,7 +90,15 @@ var authTests = []authTest{
 		false,
 	},
 	{
-		LoginAuth("user", "pass", "testserver"),
+		LoginAuth("user", "pass", "testserver", true),
+		[]string{"Username:", "Password:"},
+		"LOGIN",
+		[]string{"", "user", "pass"},
+		[]bool{false, false},
+		false,
+	},
+	{
+		LoginAuth("user", "pass", "testserver", false),
 		[]string{"User Name\x00", "Password\x00"},
 		"LOGIN",
 		[]string{"", "user", "pass"},
@@ -90,7 +106,7 @@ var authTests = []authTest{
 		false,
 	},
 	{
-		LoginAuth("user", "pass", "testserver"),
+		LoginAuth("user", "pass", "testserver", false),
 		[]string{"Invalid", "Invalid:"},
 		"LOGIN",
 		[]string{"", "user", "pass"},
@@ -98,7 +114,7 @@ var authTests = []authTest{
 		false,
 	},
 	{
-		LoginAuth("user", "pass", "testserver"),
+		LoginAuth("user", "pass", "testserver", false),
 		[]string{"Invalid", "Invalid:", "Too many"},
 		"LOGIN",
 		[]string{"", "user", "pass", ""},
@@ -237,7 +253,47 @@ func TestAuthPlain(t *testing.T) {
 		},
 	}
 	for i, tt := range tests {
-		auth := PlainAuth("foo", "bar", "baz", tt.authName)
+		auth := PlainAuth("foo", "bar", "baz", tt.authName, false)
+		_, _, err := auth.Start(tt.server)
+		got := ""
+		if err != nil {
+			got = err.Error()
+		}
+		if got != tt.err {
+			t.Errorf("%d. got error = %q; want %q", i, got, tt.err)
+		}
+	}
+}
+
+func TestAuthPlainNoEnc(t *testing.T) {
+	tests := []struct {
+		authName string
+		server   *ServerInfo
+		err      string
+	}{
+		{
+			authName: "servername",
+			server:   &ServerInfo{Name: "servername", TLS: true},
+		},
+		{
+			// OK to use PlainAuth on localhost without TLS
+			authName: "localhost",
+			server:   &ServerInfo{Name: "localhost", TLS: false},
+		},
+		{
+			// Also OK on non-TLS secured connections. The NoEnc mechanism is meant to allow
+			// non-encrypted connections.
+			authName: "servername",
+			server:   &ServerInfo{Name: "servername", Auth: []string{"PLAIN"}},
+		},
+		{
+			authName: "servername",
+			server:   &ServerInfo{Name: "attacker", TLS: true},
+			err:      "wrong host name",
+		},
+	}
+	for i, tt := range tests {
+		auth := PlainAuth("foo", "bar", "baz", tt.authName, true)
 		_, _, err := auth.Start(tt.server)
 		got := ""
 		if err != nil {
@@ -283,7 +339,51 @@ func TestAuthLogin(t *testing.T) {
 		},
 	}
 	for i, tt := range tests {
-		auth := LoginAuth("foo", "bar", tt.authName)
+		auth := LoginAuth("foo", "bar", tt.authName, false)
+		_, _, err := auth.Start(tt.server)
+		got := ""
+		if err != nil {
+			got = err.Error()
+		}
+		if got != tt.err {
+			t.Errorf("%d. got error = %q; want %q", i, got, tt.err)
+		}
+	}
+}
+
+func TestAuthLoginNoEnc(t *testing.T) {
+	tests := []struct {
+		authName string
+		server   *ServerInfo
+		err      string
+	}{
+		{
+			authName: "servername",
+			server:   &ServerInfo{Name: "servername", TLS: true},
+		},
+		{
+			// OK to use LoginAuth on localhost without TLS
+			authName: "localhost",
+			server:   &ServerInfo{Name: "localhost", TLS: false},
+		},
+		{
+			// Also OK on non-TLS secured connections. The NoEnc mechanism is meant to allow
+			// non-encrypted connections.
+			authName: "servername",
+			server:   &ServerInfo{Name: "servername", Auth: []string{"LOGIN"}},
+		},
+		{
+			authName: "servername",
+			server:   &ServerInfo{Name: "servername", Auth: []string{"CRAM-MD5"}},
+		},
+		{
+			authName: "servername",
+			server:   &ServerInfo{Name: "attacker", TLS: true},
+			err:      "wrong host name",
+		},
+	}
+	for i, tt := range tests {
+		auth := LoginAuth("foo", "bar", tt.authName, true)
 		_, _, err := auth.Start(tt.server)
 		got := ""
 		if err != nil {
@@ -317,7 +417,11 @@ func TestXOAuth2OK(t *testing.T) {
 	if err != nil {
 		t.Fatalf("NewClient: %v", err)
 	}
-	defer c.Close()
+	defer func() {
+		if err := c.Close(); err != nil {
+			t.Errorf("failed to close client: %s", err)
+		}
+	}()
 
 	auth := XOAuth2Auth("user", "token")
 	err = c.Auth(auth)
@@ -355,7 +459,11 @@ func TestXOAuth2Error(t *testing.T) {
 	if err != nil {
 		t.Fatalf("NewClient: %v", err)
 	}
-	defer c.Close()
+	defer func() {
+		if err := c.Close(); err != nil {
+			t.Errorf("failed to close client: %s", err)
+		}
+	}()
 
 	auth := XOAuth2Auth("user", "token")
 	err = c.Auth(auth)
@@ -707,7 +815,7 @@ func TestBasic(t *testing.T) {
 	// fake TLS so authentication won't complain
 	c.tls = true
 	c.serverName = "smtp.google.com"
-	if err := c.Auth(PlainAuth("", "user", "pass", "smtp.google.com")); err != nil {
+	if err := c.Auth(PlainAuth("", "user", "pass", "smtp.google.com", false)); err != nil {
 		t.Fatalf("AUTH failed: %s", err)
 	}
 
@@ -792,6 +900,35 @@ Goodbye.
 QUIT
 `
 
+func TestHELOFailed(t *testing.T) {
+	serverLines := `502 EH?
+502 EH?
+221 OK
+`
+	clientLines := `EHLO localhost
+HELO localhost
+QUIT
+`
+	server := strings.Join(strings.Split(serverLines, "\n"), "\r\n")
+	client := strings.Join(strings.Split(clientLines, "\n"), "\r\n")
+	var cmdbuf strings.Builder
+	bcmdbuf := bufio.NewWriter(&cmdbuf)
+	var fake faker
+	fake.ReadWriter = bufio.NewReadWriter(bufio.NewReader(strings.NewReader(server)), bcmdbuf)
+	c := &Client{Text: textproto.NewConn(fake), localName: "localhost"}
+	if err := c.Hello("localhost"); err == nil {
+		t.Fatal("expected EHLO to fail")
+	}
+	if err := c.Quit(); err != nil {
+		t.Errorf("QUIT failed: %s", err)
+	}
+	_ = bcmdbuf.Flush()
+	actual := cmdbuf.String()
+	if client != actual {
+		t.Errorf("Got:\n%s\nWant:\n%s", actual, client)
+	}
+}
+
 func TestExtensions(t *testing.T) {
 	fake := func(server string) (c *Client, bcmdbuf *bufio.Writer, cmdbuf *strings.Builder) {
 		server = strings.Join(strings.Split(server, "\n"), "\r\n")
@@ -1111,6 +1248,32 @@ func TestClient_SetLogger(t *testing.T) {
 	c.logger.Debugf(log.Log{Direction: log.DirServerToClient, Format: "%s", Messages: []interface{}{"test"}})
 }
 
+func TestClient_SetLogAuthData(t *testing.T) {
+	server := strings.Join(strings.Split(newClientServer, "\n"), "\r\n")
+
+	var cmdbuf strings.Builder
+	bcmdbuf := bufio.NewWriter(&cmdbuf)
+	out := func() string {
+		if err := bcmdbuf.Flush(); err != nil {
+			t.Errorf("failed to flush: %s", err)
+		}
+		return cmdbuf.String()
+	}
+	var fake faker
+	fake.ReadWriter = bufio.NewReadWriter(bufio.NewReader(strings.NewReader(server)), bcmdbuf)
+	c, err := NewClient(fake, "fake.host")
+	if err != nil {
+		t.Fatalf("NewClient: %v\n(after %v)", err, out())
+	}
+	defer func() {
+		_ = c.Close()
+	}()
+	c.SetLogAuthData()
+	if !c.logAuthData {
+		t.Error("Expected logAuthData to be true but received false")
+	}
+}
+
 var newClientServer = `220 hello world
 250-mx.google.com at your service
 250-SIZE 35651584
@@ -1252,7 +1415,7 @@ func TestHello(t *testing.T) {
 		case 3:
 			c.tls = true
 			c.serverName = "smtp.google.com"
-			err = c.Auth(PlainAuth("", "user", "pass", "smtp.google.com"))
+			err = c.Auth(PlainAuth("", "user", "pass", "smtp.google.com", false))
 		case 4:
 			err = c.Mail("test@example.com")
 		case 5:
@@ -1497,7 +1660,7 @@ func TestSendMailWithAuth(t *testing.T) {
 		}
 	}()
 
-	err = SendMail(l.Addr().String(), PlainAuth("", "user", "pass", "smtp.google.com"), "test@example.com", []string{"other@example.com"}, []byte(strings.Replace(`From: test@example.com
+	err = SendMail(l.Addr().String(), PlainAuth("", "user", "pass", "smtp.google.com", false), "test@example.com", []string{"other@example.com"}, []byte(strings.Replace(`From: test@example.com
 To: other@example.com
 Subject: SendMail test
 
@@ -1505,6 +1668,7 @@ SendMail is working for me.
 `, "\n", "\r\n", -1)))
 	if err == nil {
 		t.Error("SendMail: Server doesn't support AUTH, expected to get an error, but got none ")
+		return
 	}
 	if err.Error() != "smtp: server doesn't support AUTH" {
 		t.Errorf("Expected: smtp: server doesn't support AUTH, got: %s", err)
@@ -1532,7 +1696,7 @@ func TestAuthFailed(t *testing.T) {
 
 	c.tls = true
 	c.serverName = "smtp.google.com"
-	err = c.Auth(PlainAuth("", "user", "pass", "smtp.google.com"))
+	err = c.Auth(PlainAuth("", "user", "pass", "smtp.google.com", false))
 
 	if err == nil {
 		t.Error("Auth: expected error; got none")
@@ -2137,7 +2301,7 @@ func SkipFlaky(t testing.TB, issue int) {
 }
 
 // testSCRAMSMTPServer represents a test server for SCRAM-based SMTP authentication.
-// It does not do any acutal computation of the challanges but verifies that the expected
+// It does not do any acutal computation of the challenges but verifies that the expected
 // fields are present. We have actual real authentication tests for all SCRAM modes in the
 // go-mail client_test.go
 type testSCRAMSMTPServer struct {

testdata/RFC5322-A1-1-invalid-from.eml

@@ -0,0 +1,8 @@
+From: §§§§§§§§
+To: Mary Smith <mary@example.net>
+Subject: Saying Hello
+Date: Fri, 21 Nov 1997 09:55:06 -0600
+Message-ID: <1234@local.machine.example>
+
+This is a message just to say hello.
+So, "Hello".

testdata/RFC5322-A1-1-invalid-from.eml.license

@@ -0,0 +1,3 @@
+// SPDX-FileCopyrightText: Copyright (c) 2022-2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT

testdata/RFC5322-A1-1.eml

@@ -0,0 +1,8 @@
+From: John Doe <jdoe@machine.example>
+To: Mary Smith <mary@example.net>
+Subject: Saying Hello
+Date: Fri, 21 Nov 1997 09:55:06 -0600
+Message-ID: <1234@local.machine.example>
+
+This is a message just to say hello.
+So, "Hello".

testdata/RFC5322-A1-1.eml.license

@@ -0,0 +1,3 @@
+// SPDX-FileCopyrightText: Copyright (c) 2022-2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT

testdata/attachment

@@ -0,0 +1 @@
+This is a test attachment

testdata/attachment.license

@@ -0,0 +1,3 @@
+// SPDX-FileCopyrightText: Copyright (c) 2022-2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT

testdata/attachment.txt

@@ -0,0 +1 @@
+This is a test attachment

testdata/attachment.txt.license

@@ -0,0 +1,3 @@
+// SPDX-FileCopyrightText: Copyright (c) 2022-2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT

testdata/embed.txt

@@ -0,0 +1 @@
+This is a test embed

testdata/embed.txt.license

@@ -0,0 +1,3 @@
+// SPDX-FileCopyrightText: Copyright (c) 2022-2024 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT

testdata/logo.svg.base64

@@ -0,0 +1,367 @@
+PD94bWwgdmVyc2lvbj0iMS4wIiBlbmNvZGluZz0iVVRGLTgiIHN0YW5kYWxvbmU9Im5vIj8+PCFE
+T0NUWVBFIHN2ZyBQVUJMSUMgIi0vL1czQy8vRFREIFNWRyAxLjEvL0VOIiAiaHR0cDovL3d3dy53
+My5vcmcvR3JhcGhpY3MvU1ZHLzEuMS9EVEQvc3ZnMTEuZHRkIj48c3ZnIHdpZHRoPSIxMDAlIiBo
+ZWlnaHQ9IjEwMCUiIHZpZXdCb3g9IjAgMCA2MDAgNjAwIiB2ZXJzaW9uPSIxLjEiIHhtbG5zPSJo
+dHRwOi8vd3d3LnczLm9yZy8yMDAwL3N2ZyIgeG1sbnM6eGxpbms9Imh0dHA6Ly93d3cudzMub3Jn
+LzE5OTkveGxpbmsiIHhtbDpzcGFjZT0icHJlc2VydmUiIHhtbG5zOnNlcmlmPSJodHRwOi8vd3d3
+LnNlcmlmLmNvbS8iIHN0eWxlPSJmaWxsLXJ1bGU6ZXZlbm9kZDtjbGlwLXJ1bGU6ZXZlbm9kZDtz
+dHJva2UtbGluZWNhcDpyb3VuZDtzdHJva2UtbGluZWpvaW46cm91bmQ7c3Ryb2tlLW1pdGVybGlt
+aXQ6MS41OyI+PHJlY3QgaWQ9ItCc0L7QvdGC0LDQttC90LDRjy3QvtCx0LvQsNGB0YLRjDEiIHNl
+cmlmOmlkPSLQnNC+0L3RgtCw0LbQvdCw0Y8g0L7QsdC70LDRgdGC0YwxIiB4PSIwIiB5PSIwIiB3
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testdata/logo.svg.base64.license

@@ -0,0 +1,3 @@
+SPDX-FileCopyrightText: 2022 Maria Letta, the go-mail Team
+
+SPDX-License-Identifier: CC-BY-ND-4.0

testdata/logo.svg.license

@@ -0,0 +1,3 @@
+SPDX-FileCopyrightText: 2022 Maria Letta, the go-mail Team
+
+SPDX-License-Identifier: CC-BY-ND-4.0

util_test.go

@@ -19,7 +19,7 @@ const (
 	keyECDSAFilePath  = "dummy-child-key-ecdsa.pem"
 )
 
-// getDummyRSACryptoMaterial loads a certificate (RSA) and the associated private key (ECDSA) form local disk for testing purposes
+// getDummyRSACryptoMaterial loads a certificate (RSA), the associated private key and certificate (RSA) is loaded from local disk for testing purposes
 func getDummyRSACryptoMaterial() (*rsa.PrivateKey, *x509.Certificate, *x509.Certificate, error) {
 	keyPair, err := tls.LoadX509KeyPair(certRSAFilePath, keyRSAFilePath)
 	if err != nil {
@@ -41,7 +41,7 @@ func getDummyRSACryptoMaterial() (*rsa.PrivateKey, *x509.Certificate, *x509.Cert
 	return privateKey, certificate, intermediateCertificate, nil
 }
 
-// getDummyECDSACryptoMaterial loads a certificate (ECDSA) and the associated private key (ECDSA) form local disk for testing purposes
+// getDummyECDSACryptoMaterial loads a certificate (ECDSA), the associated private key and certificate (ECDSA) is loaded from local disk for testing purposes
 func getDummyECDSACryptoMaterial() (*ecdsa.PrivateKey, *x509.Certificate, *x509.Certificate, error) {
 	keyPair, err := tls.LoadX509KeyPair(certECDSAFilePath, keyECDSAFilePath)
 	if err != nil {
@@ -62,3 +62,12 @@ func getDummyECDSACryptoMaterial() (*ecdsa.PrivateKey, *x509.Certificate, *x509.
 
 	return privateKey, certificate, intermediateCertificate, nil
 }
+
+// getDummyKeyPairTLS loads a certificate (ECDSA) as *tls.Certificate, the associated private key and certificate (ECDSA) is loaded from local disk for testing purposes
+func getDummyKeyPairTLS() (*tls.Certificate, error) {
+	keyPair, err := tls.LoadX509KeyPair(certECDSAFilePath, keyECDSAFilePath)
+	if err != nil {
+		return nil, err
+	}
+	return &keyPair, err
+}