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diff --git a/spec/initializers/mail_encoding_patch_spec.rb b/spec/initializers/mail_encoding_patch_spec.rb
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+++ b/spec/initializers/mail_encoding_patch_spec.rb
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+# frozen_string_literal: true
+
+require 'fast_spec_helper'
+
+require 'mail'
+require_relative '../../config/initializers/mail_encoding_patch.rb'
+
+describe 'Mail quoted-printable transfer encoding patch and Unicode characters' do
+  shared_examples 'email encoding' do |email|
+    it 'enclosing in a new object does not change the encoded original' do
+      new_email = Mail.new(email)
+
+      expect(new_email.subject).to eq(email.subject)
+      expect(new_email.from).to eq(email.from)
+      expect(new_email.to).to eq(email.to)
+      expect(new_email.content_type).to eq(email.content_type)
+      expect(new_email.content_transfer_encoding).to eq(email.content_transfer_encoding)
+
+      expect(new_email.encoded).to eq(email.encoded)
+    end
+  end
+
+  context 'with a text email' do
+    context 'with a body that encodes to exactly 74 characters (final newline)' do
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+        content_type 'text/plain; charset=UTF-8'
+        content_transfer_encoding 'quoted-printable'
+        body "-123456789-123456789-123456789-123456789-123456789-123456789-123456789-1\n"
+      end
+
+      it_behaves_like 'email encoding', email
+    end
+
+    context 'with a body that encodes to exactly 74 characters (no final newline)' do
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+        content_type 'text/plain; charset=UTF-8'
+        content_transfer_encoding 'quoted-printable'
+        body "-123456789-123456789-123456789-123456789-123456789-123456789-123456789-12"
+      end
+
+      it_behaves_like 'email encoding', email
+    end
+
+    context 'with a body that encodes to exactly 75 characters' do
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+        content_type 'text/plain; charset=UTF-8'
+        content_transfer_encoding 'quoted-printable'
+        body "-123456789-123456789-123456789-123456789-123456789-123456789-123456789-12\n"
+      end
+
+      it_behaves_like 'email encoding', email
+    end
+  end
+
+  context 'with an html email' do
+    context 'with a body that encodes to exactly 74 characters (final newline)' do
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+        content_type 'text/html; charset=UTF-8'
+        content_transfer_encoding 'quoted-printable'
+        body "<p>-123456789-123456789-123456789-123456789-123456789-123456789-1234</p>\n"
+      end
+
+      it_behaves_like 'email encoding', email
+    end
+
+    context 'with a body that encodes to exactly 74 characters (no final newline)' do
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+        content_type 'text/html; charset=UTF-8'
+        content_transfer_encoding 'quoted-printable'
+        body "<p>-123456789-123456789-123456789-123456789-123456789-123456789-12345</p>"
+      end
+
+      it_behaves_like 'email encoding', email
+    end
+
+    context 'with a body that encodes to exactly 75 characters' do
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+        content_type 'text/html; charset=UTF-8'
+        content_transfer_encoding 'quoted-printable'
+        body "<p>-123456789-123456789-123456789-123456789-123456789-123456789-12345</p>\n"
+      end
+
+      it_behaves_like 'email encoding', email
+    end
+  end
+
+  context 'a multipart email' do
+    email = Mail.new do
+      to 'jane.doe@example.com'
+      from 'John Dóe <john.doe@example.com>'
+      subject 'Encoding tést'
+    end
+
+    text_part = Mail::Part.new do
+      content_type 'text/plain; charset=UTF-8'
+      content_transfer_encoding 'quoted-printable'
+      body "\r\n\r\n@john.doe, now known as John Dóe has accepted your invitation to join the Administrator / htmltest project.\r\n\r\nhttp://169.254.169.254:3000/root/htmltest\r\n\r\n-- \r\nYou're receiving this email because of your account on 169.254.169.254.\r\n\r\n\r\n\r\n"
+    end
+
+    html_part = Mail::Part.new do
+      content_type 'text/html; charset=UTF-8'
+      content_transfer_encoding 'quoted-printable'
+      body "\r\n\r\n@john.doe, now known as John Dóe has accepted your invitation to join the Administrator / htmltest project.\r\n\r\nhttp://169.254.169.254:3000/root/htmltest\r\n\r\n-- \r\nYou're receiving this email because of your account on 169.254.169.254.\r\n\r\n\r\n\r\n"
+    end
+
+    email.text_part = text_part
+    email.html_part = html_part
+
+    it_behaves_like 'email encoding', email
+  end
+
+  context 'with non UTF-8 charset' do
+    email = Mail.new do
+      to 'jane.doe@example.com'
+      from 'John Dóe <john.doe@example.com>'
+      subject 'Encoding tést'
+      content_type 'text/plain; charset=windows-1251'
+      content_transfer_encoding 'quoted-printable'
+      body "This line is very long and will be put in multiple quoted-printable lines. Some Russian character: Д\n\n\n".encode('windows-1251')
+    end
+
+    it_behaves_like 'email encoding', email
+
+    it 'can be decoded back' do
+      expect(Mail.new(email).body.decoded.dup.force_encoding('windows-1251').encode('utf-8')).to include('Some Russian character: Д')
+    end
+  end
+
+  context 'with binary content' do
+    context 'can be encoded with \'base64\' content-transfer-encoding' do
+      image = File.binread('spec/fixtures/rails_sample.jpg')
+
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+      end
+
+      part = Mail::Part.new
+      part.body = [image].pack('m')
+      part.content_type = 'image/jpg'
+      part.content_transfer_encoding = 'base64'
+
+      email.parts << part
+
+      it_behaves_like 'email encoding', email
+
+      it 'binary contents are not modified' do
+        expect(email.parts.first.decoded).to eq(image)
+
+        # Enclosing in a new Mail object does not corrupt encoded data
+        expect(Mail.new(email).parts.first.decoded).to eq(image)
+      end
+    end
+
+    context 'encoding fails with \'quoted-printable\' content-transfer-encoding' do
+      image = File.binread('spec/fixtures/rails_sample.jpg')
+
+      email = Mail.new do
+        to 'jane.doe@example.com'
+        from 'John Dóe <john.doe@example.com>'
+        subject 'Encoding tést'
+      end
+
+      part = Mail::Part.new
+      part.body = [image].pack('M*')
+      part.content_type = 'image/jpg'
+      part.content_transfer_encoding = 'quoted-printable'
+
+      email.parts << part
+
+      # The Mail patch in `config/initializers/mail_encoding_patch.rb` fixes
+      # encoding of non-binary content. The failure below is expected since we
+      # reverted some upstream changes in order to properly support SMIME signatures
+      # See https://gitlab.com/gitlab-org/gitlab/issues/197386
+      it 'content cannot be decoded back' do
+        # Headers are ok
+        expect(email.subject).to eq(email.subject)
+        expect(email.from).to eq(email.from)
+        expect(email.to).to eq(email.to)
+        expect(email.content_type).to eq(email.content_type)
+        expect(email.content_transfer_encoding).to eq(email.content_transfer_encoding)
+
+        # Content cannot be recovered
+        expect(email.parts.first.decoded).not_to eq(image)
+      end
+    end
+  end
+end