From dde5c46a3eb7c6dcee47795590619ccd393577d2 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?C=C3=B4me=20Chilliet?= <come.chilliet@nextcloud.com>
Date: Mon, 20 Dec 2021 11:35:06 +0100
Subject: [PATCH 1/2] Migrate to Symfony Mailer
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Signed-off-by: Côme Chilliet <come.chilliet@nextcloud.com>
---
 3rdparty                                      |   2 +-
 apps/dav/lib/CalDAV/Schedule/IMipPlugin.php   |   7 +-
 .../lib/Controller/MailSettingsController.php |   2 -
 apps/settings/lib/Settings/Admin/Mail.php     |   1 -
 .../settings/admin/additional-mail.php        |  33 +-
 .../Controller/MailSettingsControllerTest.php |   4 -
 .../tests/Settings/Admin/MailTest.php         |   2 -
 config/config.sample.php                      |  23 +-
 lib/private/Mail/Attachment.php               |  36 +-
 lib/private/Mail/Mailer.php                   | 172 ++++----
 lib/private/Mail/Message.php                  | 188 ++++-----
 lib/public/Mail/IMailer.php                   |   2 +-
 tests/lib/Mail/MailerTest.php                 | 128 ++++--
 tests/lib/Mail/MessageTest.php                | 366 +++++++-----------
 14 files changed, 480 insertions(+), 486 deletions(-)

diff --git a/3rdparty b/3rdparty
index 1d53ed4d32824..b31aba0505a3d 160000
--- a/3rdparty
+++ b/3rdparty
@@ -1 +1 @@
-Subproject commit 1d53ed4d3282427854fca7ee6ecbb945304272db
+Subproject commit b31aba0505a3daf84b016f52873794b618694dff
diff --git a/apps/dav/lib/CalDAV/Schedule/IMipPlugin.php b/apps/dav/lib/CalDAV/Schedule/IMipPlugin.php
index be238ae5afbda..50390549570dc 100644
--- a/apps/dav/lib/CalDAV/Schedule/IMipPlugin.php
+++ b/apps/dav/lib/CalDAV/Schedule/IMipPlugin.php
@@ -172,9 +172,14 @@ public function schedule(Message $iTipMessage) {
 			return;
 		}
 
-		$senderName = $iTipMessage->senderName ?: null;
 		$recipientName = $iTipMessage->recipientName ?: null;
 
+		/** @var Parameter|string|null $senderName */
+		$senderName = $iTipMessage->senderName ?: null;
+		if($senderName instanceof Parameter) {
+			$senderName = $senderName->getValue() ?? null;
+		}
+
 		if ($senderName === null || empty(trim($senderName))) {
 			$senderName = $this->userManager->getDisplayName($this->userId);
 		}
diff --git a/apps/settings/lib/Controller/MailSettingsController.php b/apps/settings/lib/Controller/MailSettingsController.php
index 22c0622a0722d..2df79b6773133 100644
--- a/apps/settings/lib/Controller/MailSettingsController.php
+++ b/apps/settings/lib/Controller/MailSettingsController.php
@@ -85,7 +85,6 @@ public function __construct($appName,
 	 * @param string $mail_smtpmode
 	 * @param string $mail_smtpsecure
 	 * @param string $mail_smtphost
-	 * @param string $mail_smtpauthtype
 	 * @param int $mail_smtpauth
 	 * @param string $mail_smtpport
 	 * @return DataResponse
@@ -95,7 +94,6 @@ public function setMailSettings($mail_domain,
 									$mail_smtpmode,
 									$mail_smtpsecure,
 									$mail_smtphost,
-									$mail_smtpauthtype,
 									$mail_smtpauth,
 									$mail_smtpport,
 									$mail_sendmailmode) {
diff --git a/apps/settings/lib/Settings/Admin/Mail.php b/apps/settings/lib/Settings/Admin/Mail.php
index f4c546b27a42f..1cdb7315713c6 100644
--- a/apps/settings/lib/Settings/Admin/Mail.php
+++ b/apps/settings/lib/Settings/Admin/Mail.php
@@ -61,7 +61,6 @@ public function getForm() {
 			'mail_smtpsecure' => $this->config->getSystemValue('mail_smtpsecure', ''),
 			'mail_smtphost' => $this->config->getSystemValue('mail_smtphost', ''),
 			'mail_smtpport' => $this->config->getSystemValue('mail_smtpport', ''),
-			'mail_smtpauthtype' => $this->config->getSystemValue('mail_smtpauthtype', ''),
 			'mail_smtpauth' => $this->config->getSystemValue('mail_smtpauth', false),
 			'mail_smtpname' => $this->config->getSystemValue('mail_smtpname', ''),
 			'mail_smtppassword' => $this->config->getSystemValue('mail_smtppassword', ''),
diff --git a/apps/settings/templates/settings/admin/additional-mail.php b/apps/settings/templates/settings/admin/additional-mail.php
index 6b85fcbe86753..6b31ebe879cfd 100644
--- a/apps/settings/templates/settings/admin/additional-mail.php
+++ b/apps/settings/templates/settings/admin/additional-mail.php
@@ -24,17 +24,9 @@
 /** @var \OCP\IL10N $l */
 /** @var array $_ */
 
-$mail_smtpauthtype = [
-	'' => $l->t('None'),
-	'LOGIN' => $l->t('Login'),
-	'PLAIN' => $l->t('Plain'),
-	'NTLM' => $l->t('NT LAN Manager'),
-];
-
 $mail_smtpsecure = [
 	'' => $l->t('None'),
-	'ssl' => $l->t('SSL/TLS'),
-	'tls' => $l->t('STARTTLS'),
+	'ssl' => $l->t('SSL/TLS')
 ];
 
 $mail_smtpmode = [
@@ -112,26 +104,7 @@
 				   value="<?php p($_['mail_domain']) ?>" />
 		</p>
 
-		<p id="setting_smtpauth" <?php if ($_['mail_smtpmode'] !== 'smtp') {
-						print_unescaped(' class="hidden"');
-					} ?>>
-			<label for="mail_smtpauthtype"><?php p($l->t('Authentication method')); ?></label>
-			<select name="mail_smtpauthtype" id="mail_smtpauthtype">
-				<?php foreach ($mail_smtpauthtype as $authtype => $name):
-					$selected = '';
-					if ($authtype == $_['mail_smtpauthtype']):
-						$selected = 'selected="selected"';
-					endif; ?>
-					<option value="<?php p($authtype)?>" <?php p($selected) ?>><?php p($name) ?></option>
-				<?php endforeach;?>
-			</select>
-
-			<input type="checkbox" name="mail_smtpauth" id="mail_smtpauth" class="checkbox" value="1"
-				<?php if ($_['mail_smtpauth']) {
-						print_unescaped('checked="checked"');
-					} ?> />
-			<label for="mail_smtpauth"><?php p($l->t('Authentication required')); ?></label>
-		</p>
+<!--lo-->
 
 		<p id="setting_smtphost" <?php if ($_['mail_smtpmode'] !== 'smtp') {
 						print_unescaped(' class="hidden"');
@@ -145,7 +118,7 @@
 		</p>
 	</form>
 	<form class="mail_settings" id="mail_credentials_settings">
-		<p id="mail_credentials" <?php if (!$_['mail_smtpauth'] || $_['mail_smtpmode'] !== 'smtp') {
+		<p id="mail_credentials" <?php if ($_['mail_smtpmode'] !== 'smtp') {
 						print_unescaped(' class="hidden"');
 					} ?>>
 			<label for="mail_smtpname"><?php p($l->t('Credentials')); ?></label>
diff --git a/apps/settings/tests/Controller/MailSettingsControllerTest.php b/apps/settings/tests/Controller/MailSettingsControllerTest.php
index 54461201201a0..db6043030d3cb 100644
--- a/apps/settings/tests/Controller/MailSettingsControllerTest.php
+++ b/apps/settings/tests/Controller/MailSettingsControllerTest.php
@@ -91,7 +91,6 @@ public function testSetMailSettings() {
 					'mail_smtpmode' => 'smtp',
 					'mail_smtpsecure' => 'ssl',
 					'mail_smtphost' => 'mx.nextcloud.org',
-					'mail_smtpauthtype' => 'NTLM',
 					'mail_smtpauth' => 1,
 					'mail_smtpport' => '25',
 					'mail_sendmailmode' => null,
@@ -102,7 +101,6 @@ public function testSetMailSettings() {
 					'mail_smtpmode' => 'smtp',
 					'mail_smtpsecure' => 'ssl',
 					'mail_smtphost' => 'mx.nextcloud.org',
-					'mail_smtpauthtype' => 'NTLM',
 					'mail_smtpauth' => null,
 					'mail_smtpport' => '25',
 					'mail_smtpname' => null,
@@ -118,7 +116,6 @@ public function testSetMailSettings() {
 			'smtp',
 			'ssl',
 			'mx.nextcloud.org',
-			'NTLM',
 			1,
 			'25',
 			null
@@ -132,7 +129,6 @@ public function testSetMailSettings() {
 			'smtp',
 			'ssl',
 			'mx.nextcloud.org',
-			'NTLM',
 			0,
 			'25',
 			null
diff --git a/apps/settings/tests/Settings/Admin/MailTest.php b/apps/settings/tests/Settings/Admin/MailTest.php
index 7a70065ff5022..c3b08a9d50906 100644
--- a/apps/settings/tests/Settings/Admin/MailTest.php
+++ b/apps/settings/tests/Settings/Admin/MailTest.php
@@ -64,7 +64,6 @@ public function testGetForm() {
 				['mail_smtpsecure', '', true],
 				['mail_smtphost', '', 'smtp.nextcloud.com'],
 				['mail_smtpport', '', 25],
-				['mail_smtpauthtype', '', 'login'],
 				['mail_smtpauth', false, true],
 				['mail_smtpname', '', 'smtp.sender.com'],
 				['mail_smtppassword', '', 'mypassword'],
@@ -82,7 +81,6 @@ public function testGetForm() {
 				'mail_smtpsecure' => true,
 				'mail_smtphost' => 'smtp.nextcloud.com',
 				'mail_smtpport' => 25,
-				'mail_smtpauthtype' => 'login',
 				'mail_smtpauth' => true,
 				'mail_smtpname' => 'smtp.sender.com',
 				'mail_smtppassword' => '********',
diff --git a/config/config.sample.php b/config/config.sample.php
index f7861c3c94c47..806345092f263 100644
--- a/config/config.sample.php
+++ b/config/config.sample.php
@@ -463,14 +463,17 @@
 'mail_smtptimeout' => 10,
 
 /**
- * This depends on ``mail_smtpmode``. Specify when you are using ``ssl`` for SSL/TLS or
- * ``tls`` for STARTTLS, or leave empty for no encryption.
+ * This depends on ``mail_smtpmode``. Specify ``ssl`` when you are using SSL/TLS. Any other value will be ignored.
+ *
+ * If the server advertises STARTTLS capabilities, they might be used, but they cannot be enforced by
+ * this config option.
  *
  * Defaults to ``''`` (empty string)
  */
 'mail_smtpsecure' => '',
 
 /**
+ *
  * This depends on ``mail_smtpmode``. Change this to ``true`` if your mail
  * server requires authentication.
  *
@@ -478,14 +481,6 @@
  */
 'mail_smtpauth' => false,
 
-/**
- * This depends on ``mail_smtpmode``. If SMTP authentication is required, choose
- * the authentication type as ``LOGIN`` or ``PLAIN``.
- *
- * Defaults to ``LOGIN``
- */
-'mail_smtpauthtype' => 'LOGIN',
-
 /**
  * This depends on ``mail_smtpauth``. Specify the username for authenticating to
  * the SMTP server.
@@ -1190,14 +1185,14 @@
 'preview_office_cl_parameters' =>
 	' --headless --nologo --nofirststartwizard --invisible --norestore '.
 	'--convert-to png --outdir ',
-	
+
 /**
  * custom path for ffmpeg binary
- * 
+ *
  * Defaults to ``null`` and falls back to searching ``avconv`` and ``ffmpeg`` in the configured ``PATH`` environment
  */
-'preview_ffmpeg_path' => '/usr/bin/ffmpeg',	
-	
+'preview_ffmpeg_path' => '/usr/bin/ffmpeg',
+
 /**
  * Set the URL of the Imaginary service to send image previews to.
  * Also requires the ``OC\Preview\Imaginary`` provider to be enabled.
diff --git a/lib/private/Mail/Attachment.php b/lib/private/Mail/Attachment.php
index 12f71df86d9f3..5bfe0dd0522b3 100644
--- a/lib/private/Mail/Attachment.php
+++ b/lib/private/Mail/Attachment.php
@@ -27,6 +27,7 @@
 namespace OC\Mail;
 
 use OCP\Mail\IAttachment;
+use Symfony\Component\Mime\Email;
 
 /**
  * Class Attachment
@@ -35,11 +36,21 @@
  * @since 13.0.0
  */
 class Attachment implements IAttachment {
-	/** @var \Swift_Mime_Attachment */
-	protected $swiftAttachment;
+	private ?string $body;
+	private ?string $name;
+	private ?string $contentType;
+	private ?string $path;
 
-	public function __construct(\Swift_Mime_Attachment $attachment) {
-		$this->swiftAttachment = $attachment;
+	public function __construct(
+		?string $body,
+		?string $name,
+		?string $contentType,
+		?string $path = null
+	) {
+		$this->body = $body;
+		$this->name = $name;
+		$this->contentType = $contentType;
+		$this->path = $path;
 	}
 
 	/**
@@ -48,7 +59,7 @@ public function __construct(\Swift_Mime_Attachment $attachment) {
 	 * @since 13.0.0
 	 */
 	public function setFilename(string $filename): IAttachment {
-		$this->swiftAttachment->setFilename($filename);
+		$this->name = $filename;
 		return $this;
 	}
 
@@ -58,7 +69,7 @@ public function setFilename(string $filename): IAttachment {
 	 * @since 13.0.0
 	 */
 	public function setContentType(string $contentType): IAttachment {
-		$this->swiftAttachment->setContentType($contentType);
+		$this->contentType = $contentType;
 		return $this;
 	}
 
@@ -68,14 +79,15 @@ public function setContentType(string $contentType): IAttachment {
 	 * @since 13.0.0
 	 */
 	public function setBody(string $body): IAttachment {
-		$this->swiftAttachment->setBody($body);
+		$this->body = $body;
 		return $this;
 	}
 
-	/**
-	 * @return \Swift_Mime_Attachment
-	 */
-	public function getSwiftAttachment(): \Swift_Mime_Attachment {
-		return $this->swiftAttachment;
+	public function attach(Email $symfonyEmail): void {
+		if ($this->path !== null) {
+			$symfonyEmail->attachFromPath($this->path, $this->name, $this->contentType);
+		} else {
+			$symfonyEmail->attach($this->body, $this->name, $this->contentType);
+		}
 	}
 }
diff --git a/lib/private/Mail/Mailer.php b/lib/private/Mail/Mailer.php
index d0c3b04eacbd7..05ef0bf513962 100644
--- a/lib/private/Mail/Mailer.php
+++ b/lib/private/Mail/Mailer.php
@@ -50,6 +50,15 @@
 use OCP\Mail\IMailer;
 use OCP\Mail\IMessage;
 use Psr\Log\LoggerInterface;
+use Symfony\Component\Mailer\Exception\TransportExceptionInterface;
+use Symfony\Component\Mailer\Mailer as SymfonyMailer;
+use Symfony\Component\Mailer\MailerInterface;
+use Symfony\Component\Mailer\Transport\SendmailTransport;
+use Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport;
+use Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mime\Exception\InvalidArgumentException;
+use Symfony\Component\Mime\Exception\RfcComplianceException;
 
 /**
  * Class Mailer provides some basic functions to create a mail message that can be used in combination with
@@ -70,12 +79,10 @@
  * @package OC\Mail
  */
 class Mailer implements IMailer {
-	/** @var \Swift_Mailer Cached mailer */
-	private $instance = null;
+	private ?MailerInterface $instance = null;
 	private IConfig $config;
 	private LoggerInterface $logger;
-	/** @var Defaults */
-	private $defaults;
+	private Defaults $defaults;
 	private IURLGenerator $urlGenerator;
 	private IL10N $l10n;
 	private IEventDispatcher $dispatcher;
@@ -100,11 +107,11 @@ public function __construct(IConfig $config,
 	/**
 	 * Creates a new message object that can be passed to send()
 	 *
-	 * @return IMessage
+	 * @return Message
 	 */
-	public function createMessage(): IMessage {
+	public function createMessage(): Message {
 		$plainTextOnly = $this->config->getSystemValue('mail_send_plaintext_only', false);
-		return new Message(new \Swift_Message(), $plainTextOnly);
+		return new Message(new Email(), $plainTextOnly);
 	}
 
 	/**
@@ -115,7 +122,7 @@ public function createMessage(): IMessage {
 	 * @since 13.0.0
 	 */
 	public function createAttachment($data = null, $filename = null, $contentType = null): IAttachment {
-		return new Attachment(new \Swift_Attachment($data, $filename, $contentType));
+		return new Attachment($data, $filename, $contentType);
 	}
 
 	/**
@@ -125,7 +132,7 @@ public function createAttachment($data = null, $filename = null, $contentType =
 	 * @since 13.0.0
 	 */
 	public function createAttachmentFromPath(string $path, $contentType = null): IAttachment {
-		return new Attachment(\Swift_Attachment::fromPath($path, $contentType));
+		return new Attachment(null, null, $contentType, $path);
 	}
 
 	/**
@@ -162,49 +169,82 @@ public function createEMailTemplate(string $emailId, array $data = []): IEMailTe
 	 * Send the specified message. Also sets the from address to the value defined in config.php
 	 * if no-one has been passed.
 	 *
-	 * @param IMessage|Message $message Message to send
-	 * @return string[] Array with failed recipients. Be aware that this depends on the used mail backend and
-	 * therefore should be considered
-	 * @throws \Exception In case it was not possible to send the message. (for example if an invalid mail address
-	 * has been supplied.)
+	 * If sending failed, the recipients that failed will be returned (to, cc and bcc).
+	 * Will output additional debug info if 'mail_smtpdebug' => 'true' is set in config.php
+	 *
+	 * @param IMessage $message Message to send
+	 * @return string[] $failedRecipients
 	 */
 	public function send(IMessage $message): array {
 		$debugMode = $this->config->getSystemValue('mail_smtpdebug', false);
 
+		if (!($message instanceof Message)) {
+			throw new InvalidArgumentException('Object not of type ' . Message::class);
+		}
+
 		if (empty($message->getFrom())) {
 			$message->setFrom([\OCP\Util::getDefaultEmailAddress('no-reply') => $this->defaults->getName()]);
 		}
 
-		$failedRecipients = [];
-
 		$mailer = $this->getInstance();
 
-		// Enable logger if debug mode is enabled
-		if ($debugMode) {
-			$mailLogger = new \Swift_Plugins_Loggers_ArrayLogger();
-			$mailer->registerPlugin(new \Swift_Plugins_LoggerPlugin($mailLogger));
-		}
+		$this->dispatcher->dispatchTyped(new BeforeMessageSent($message));
 
+		try {
+			$message->setRecipients();
+		} catch (InvalidArgumentException|RfcComplianceException $e) {
+			$logMessage = sprintf(
+				'Could not send mail to "%s" with subject "%s" as validation for address failed',
+				print_r(array_merge($message->getTo(), $message->getCc(), $message->getBcc()), true),
+				$message->getSubject()
+			);
+			$this->logger->debug($logMessage, ['app' => 'core', 'exception' => $e]);
+			$recipients = array_merge($message->getTo(), $message->getCc(), $message->getBcc());
+			$failedRecipients = [];
+
+			array_walk($recipients, function ($value, $key) use (&$failedRecipients) {
+				if (is_numeric($key)) {
+					$failedRecipients[] = $value;
+				} else {
+					$failedRecipients[] = $key;
+				}
+			});
 
-		$this->dispatcher->dispatchTyped(new BeforeMessageSent($message));
+			return $failedRecipients;
+		}
 
-		$mailer->send($message->getSwiftMessage(), $failedRecipients);
+		try {
+			$mailer->send($message->getSymfonyEmail());
+		} catch (TransportExceptionInterface $e) {
+			$logMessage = sprintf('Sending mail to "%s" with subject "%s" failed', print_r($message->getTo(), true), $message->getSubject());
+			$this->logger->debug($logMessage, ['app' => 'core', 'exception' => $e]);
+			if ($debugMode) {
+				$this->logger->debug($e->getDebug(), ['app' => 'core']);
+			}
+			$recipients = array_merge($message->getTo(), $message->getCc(), $message->getBcc());
+			$failedRecipients = [];
+
+			array_walk($recipients, function ($value, $key) use (&$failedRecipients) {
+				if (is_numeric($key)) {
+					$failedRecipients[] = $value;
+				} else {
+					$failedRecipients[] = $key;
+				}
+			});
+
+			return $failedRecipients;
+		}
 
 		// Debugging logging
 		$logMessage = sprintf('Sent mail to "%s" with subject "%s"', print_r($message->getTo(), true), $message->getSubject());
-		if (!empty($failedRecipients)) {
-			$logMessage .= sprintf(' (failed for "%s")', print_r($failedRecipients, true));
-		}
 		$this->logger->debug($logMessage, ['app' => 'core']);
-		if ($debugMode && isset($mailLogger)) {
-			$this->logger->debug($mailLogger->dump(), ['app' => 'core']);
-		}
 
-		return $failedRecipients;
+		return [];
 	}
 
 	/**
-	 * Checks if an e-mail address is valid
+	 * @deprecated 26.0.0 Implicit validation is done in \OC\Mail\Message::setRecipients
+	 *                    via \Symfony\Component\Mime\Address::__construct
 	 *
 	 * @param string $email Email address to be validated
 	 * @return bool True if the mail address is valid, false otherwise
@@ -217,28 +257,10 @@ public function validateMailAddress(string $email): bool {
 		$validator = new EmailValidator();
 		$validation = new RFCValidation();
 
-		return $validator->isValid($this->convertEmail($email), $validation);
+		return $validator->isValid($email, $validation);
 	}
 
-	/**
-	 * SwiftMailer does currently not work with IDN domains, this function therefore converts the domains
-	 *
-	 * FIXME: Remove this once SwiftMailer supports IDN
-	 *
-	 * @param string $email
-	 * @return string Converted mail address if `idn_to_ascii` exists
-	 */
-	protected function convertEmail(string $email): string {
-		if (!function_exists('idn_to_ascii') || !defined('INTL_IDNA_VARIANT_UTS46') || strpos($email, '@') === false) {
-			return $email;
-		}
-
-		[$name, $domain] = explode('@', $email, 2);
-		$domain = idn_to_ascii($domain, 0, INTL_IDNA_VARIANT_UTS46);
-		return $name.'@'.$domain;
-	}
-
-	protected function getInstance(): \Swift_Mailer {
+	protected function getInstance(): MailerInterface {
 		if (!is_null($this->instance)) {
 			return $this->instance;
 		}
@@ -255,31 +277,47 @@ protected function getInstance(): \Swift_Mailer {
 				break;
 		}
 
-		return new \Swift_Mailer($transport);
+		return new SymfonyMailer($transport);
 	}
 
 	/**
 	 * Returns the SMTP transport
 	 *
-	 * @return \Swift_SmtpTransport
+	 * Only supports ssl/tls
+	 * starttls is not enforcable with Symfony Mailer but might be available
+	 * via the automatic config (Symfony Mailer internal)
+	 *
+	 * @return EsmtpTransport
 	 */
-	protected function getSmtpInstance(): \Swift_SmtpTransport {
-		$transport = new \Swift_SmtpTransport();
-		$transport->setTimeout($this->config->getSystemValue('mail_smtptimeout', 10));
-		$transport->setHost($this->config->getSystemValue('mail_smtphost', '127.0.0.1'));
-		$transport->setPort($this->config->getSystemValue('mail_smtpport', 25));
+	protected function getSmtpInstance(): EsmtpTransport {
+		// either null or true - if nothing is passed, let the symfony mailer figure out the configuration by itself
+		$mailSmtpsecure = ($this->config->getSystemValue('mail_smtpsecure', null) === 'ssl') ? true : null;
+		$transport = new EsmtpTransport(
+			$this->config->getSystemValue('mail_smtphost', '127.0.0.1'),
+			(int)$this->config->getSystemValue('mail_smtpport', 25),
+			$mailSmtpsecure,
+			null,
+			$this->logger
+		);
+		/** @var SocketStream $stream */
+		$stream = $transport->getStream();
+		/** @psalm-suppress InternalMethod */
+		$stream->setTimeout($this->config->getSystemValue('mail_smtptimeout', 10));
+
 		if ($this->config->getSystemValue('mail_smtpauth', false)) {
 			$transport->setUsername($this->config->getSystemValue('mail_smtpname', ''));
 			$transport->setPassword($this->config->getSystemValue('mail_smtppassword', ''));
-			$transport->setAuthMode($this->config->getSystemValue('mail_smtpauthtype', 'LOGIN'));
-		}
-		$smtpSecurity = $this->config->getSystemValue('mail_smtpsecure', '');
-		if (!empty($smtpSecurity)) {
-			$transport->setEncryption($smtpSecurity);
 		}
+
 		$streamingOptions = $this->config->getSystemValue('mail_smtpstreamoptions', []);
 		if (is_array($streamingOptions) && !empty($streamingOptions)) {
-			$transport->setStreamOptions($streamingOptions);
+			/** @psalm-suppress InternalMethod */
+			$currentStreamingOptions = $stream->getStreamOptions();
+
+			$currentStreamingOptions = array_merge_recursive($currentStreamingOptions, $streamingOptions);
+
+			/** @psalm-suppress InternalMethod */
+			$stream->setStreamOptions($currentStreamingOptions);
 		}
 
 		$overwriteCliUrl = parse_url(
@@ -297,9 +335,9 @@ protected function getSmtpInstance(): \Swift_SmtpTransport {
 	/**
 	 * Returns the sendmail transport
 	 *
-	 * @return \Swift_SendmailTransport
+	 * @return SendmailTransport
 	 */
-	protected function getSendMailInstance(): \Swift_SendmailTransport {
+	protected function getSendMailInstance(): SendmailTransport {
 		switch ($this->config->getSystemValue('mail_smtpmode', 'smtp')) {
 			case 'qmail':
 				$binaryPath = '/var/qmail/bin/sendmail';
@@ -322,6 +360,6 @@ protected function getSendMailInstance(): \Swift_SendmailTransport {
 				break;
 		}
 
-		return new \Swift_SendmailTransport($binaryPath . $binaryParam);
+		return new SendmailTransport($binaryPath . $binaryParam, null, $this->logger);
 	}
 }
diff --git a/lib/private/Mail/Message.php b/lib/private/Mail/Message.php
index 3313b39e2e2be..01beefcc6d6e2 100644
--- a/lib/private/Mail/Message.php
+++ b/lib/private/Mail/Message.php
@@ -35,64 +35,67 @@
 use OCP\Mail\IAttachment;
 use OCP\Mail\IEMailTemplate;
 use OCP\Mail\IMessage;
-use Swift_Message;
+use Symfony\Component\Mime\Address;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mime\Exception\InvalidArgumentException;
+use Symfony\Component\Mime\Exception\RfcComplianceException;
 
 /**
- * Class Message provides a wrapper around SwiftMail
+ * Class Message provides a wrapper around Symfony\Component\Mime\Email (Used to be around SwiftMail)
  *
  * @package OC\Mail
  */
 class Message implements IMessage {
-	/** @var Swift_Message */
-	private $swiftMessage;
-	/** @var bool */
-	private $plainTextOnly;
+	private Email $symfonyEmail;
+	private bool $plainTextOnly;
 
-	public function __construct(Swift_Message $swiftMessage, bool $plainTextOnly) {
-		$this->swiftMessage = $swiftMessage;
+	private array $to;
+	private array $from;
+	private array $replyTo;
+	private array $cc;
+	private array $bcc;
+
+	public function __construct(Email $symfonyEmail, bool $plainTextOnly) {
+		$this->symfonyEmail = $symfonyEmail;
 		$this->plainTextOnly = $plainTextOnly;
+		$this->to = [];
+		$this->from = [];
+		$this->replyTo = [];
+		$this->cc = [];
+		$this->bcc = [];
 	}
 
 	/**
-	 * @param IAttachment $attachment
 	 * @return $this
 	 * @since 13.0.0
 	 */
 	public function attach(IAttachment $attachment): IMessage {
 		/** @var Attachment $attachment */
-		$this->swiftMessage->attach($attachment->getSwiftAttachment());
+		$attachment->attach($this->symfonyEmail);
 		return $this;
 	}
 
 	/**
-	 * SwiftMailer does currently not work with IDN domains, this function therefore converts the domains
-	 * FIXME: Remove this once SwiftMailer supports IDN
+	 * Converts the [['displayName' => 'email'], ['displayName2' => 'email2']] arrays to valid Adresses
 	 *
-	 * @param array $addresses Array of mail addresses, key will get converted
-	 * @return array Converted addresses if `idn_to_ascii` exists
+	 * @param array $addresses Array of mail addresses
+	 * @return Address[]
+	 * @throws RfcComplianceException|InvalidArgumentException
 	 */
 	protected function convertAddresses(array $addresses): array {
-		if (!function_exists('idn_to_ascii') || !defined('INTL_IDNA_VARIANT_UTS46')) {
-			return $addresses;
-		}
-
 		$convertedAddresses = [];
 
-		foreach ($addresses as $email => $readableName) {
-			$parsableEmail = is_numeric($email) ? $readableName : $email;
-			if (strpos($parsableEmail, '@') === false) {
-				$convertedAddresses[$parsableEmail] = $readableName;
-				continue;
-			}
+		if (empty($addresses)) {
+			return [];
+		}
 
-			[$name, $domain] = explode('@', $parsableEmail, 2);
-			$domain = idn_to_ascii($domain, 0, INTL_IDNA_VARIANT_UTS46);
+		array_walk($addresses, function ($readableName, $email) use (&$convertedAddresses) {
 			if (is_numeric($email)) {
-				$convertedAddresses[] = $name . '@' . $domain;
+				$convertedAddresses[] = new Address($readableName);
 			} else {
-				$convertedAddresses[$name . '@' . $domain] = $readableName;
+				$convertedAddresses[] = new Address($email, $readableName);
 			}
-		}
+		});
 
 		return $convertedAddresses;
 	}
@@ -106,41 +109,32 @@ protected function convertAddresses(array $addresses): array {
 	 * @return $this
 	 */
 	public function setFrom(array $addresses): IMessage {
-		$addresses = $this->convertAddresses($addresses);
-
-		$this->swiftMessage->setFrom($addresses);
+		$this->from = $addresses;
 		return $this;
 	}
 
 	/**
 	 * Get the from address of this message.
-	 *
-	 * @return array
 	 */
 	public function getFrom(): array {
-		return $this->swiftMessage->getFrom() ?? [];
+		return $this->from;
 	}
 
 	/**
 	 * Set the Reply-To address of this message
 	 *
-	 * @param array $addresses
 	 * @return $this
 	 */
 	public function setReplyTo(array $addresses): IMessage {
-		$addresses = $this->convertAddresses($addresses);
-
-		$this->swiftMessage->setReplyTo($addresses);
+		$this->replyTo = $addresses;
 		return $this;
 	}
 
 	/**
 	 * Returns the Reply-To address of this message
-	 *
-	 * @return string
 	 */
-	public function getReplyTo(): string {
-		return $this->swiftMessage->getReplyTo();
+	public function getReplyTo(): array {
+		return $this->replyTo;
 	}
 
 	/**
@@ -150,19 +144,15 @@ public function getReplyTo(): string {
 	 * @return $this
 	 */
 	public function setTo(array $recipients): IMessage {
-		$recipients = $this->convertAddresses($recipients);
-
-		$this->swiftMessage->setTo($recipients);
+		$this->to = $recipients;
 		return $this;
 	}
 
 	/**
 	 * Get the to address of this message.
-	 *
-	 * @return array
 	 */
 	public function getTo(): array {
-		return $this->swiftMessage->getTo() ?? [];
+		return $this->to;
 	}
 
 	/**
@@ -172,19 +162,15 @@ public function getTo(): array {
 	 * @return $this
 	 */
 	public function setCc(array $recipients): IMessage {
-		$recipients = $this->convertAddresses($recipients);
-
-		$this->swiftMessage->setCc($recipients);
+		$this->cc = $recipients;
 		return $this;
 	}
 
 	/**
 	 * Get the cc address of this message.
-	 *
-	 * @return array
 	 */
 	public function getCc(): array {
-		return $this->swiftMessage->getCc() ?? [];
+		return $this->cc;
 	}
 
 	/**
@@ -194,104 +180,119 @@ public function getCc(): array {
 	 * @return $this
 	 */
 	public function setBcc(array $recipients): IMessage {
-		$recipients = $this->convertAddresses($recipients);
-
-		$this->swiftMessage->setBcc($recipients);
+		$this->bcc = $recipients;
 		return $this;
 	}
 
 	/**
 	 * Get the Bcc address of this message.
-	 *
-	 * @return array
 	 */
 	public function getBcc(): array {
-		return $this->swiftMessage->getBcc() ?? [];
+		return $this->bcc;
 	}
 
 	/**
 	 * Set the subject of this message.
 	 *
-	 * @param string $subject
-	 * @return IMessage
+	 * @return $this
 	 */
 	public function setSubject(string $subject): IMessage {
-		$this->swiftMessage->setSubject($subject);
+		$this->symfonyEmail->subject($subject);
 		return $this;
 	}
 
 	/**
 	 * Get the from subject of this message.
-	 *
-	 * @return string
 	 */
 	public function getSubject(): string {
-		return $this->swiftMessage->getSubject();
+		return $this->symfonyEmail->getSubject() ?? '';
 	}
 
 	/**
 	 * Set the plain-text body of this message.
-	 *
-	 * @param string $body
 	 * @return $this
 	 */
 	public function setPlainBody(string $body): IMessage {
-		$this->swiftMessage->setBody($body);
+		$this->symfonyEmail->text($body);
 		return $this;
 	}
 
 	/**
 	 * Get the plain body of this message.
-	 *
-	 * @return string
 	 */
 	public function getPlainBody(): string {
-		return $this->swiftMessage->getBody();
+		/** @var string $body */
+		$body = $this->symfonyEmail->getTextBody() ?? '';
+		return $body;
 	}
 
 	/**
 	 * Set the HTML body of this message. Consider also sending a plain-text body instead of only an HTML one.
-	 *
-	 * @param string $body
 	 * @return $this
 	 */
-	public function setHtmlBody($body) {
+	public function setHtmlBody(string $body): IMessage {
 		if (!$this->plainTextOnly) {
-			$this->swiftMessage->addPart($body, 'text/html');
+			$this->symfonyEmail->html($body);
 		}
 		return $this;
 	}
 
 	/**
-	 * Get's the underlying SwiftMessage
-	 * @param Swift_Message $swiftMessage
+	 * Set the underlying Email intance
 	 */
-	public function setSwiftMessage(Swift_Message $swiftMessage): void {
-		$this->swiftMessage = $swiftMessage;
+	public function setSymfonyEmail(Email $symfonyEmail): void {
+		$this->symfonyEmail = $symfonyEmail;
 	}
 
 	/**
-	 * Get's the underlying SwiftMessage
-	 * @return Swift_Message
+	 * Get the underlying Email instance
 	 */
-	public function getSwiftMessage(): Swift_Message {
-		return $this->swiftMessage;
+	public function getSymfonyEmail(): Email {
+		return $this->symfonyEmail;
 	}
 
 	/**
-	 * @param string $body
-	 * @param string $contentType
 	 * @return $this
 	 */
-	public function setBody($body, $contentType) {
+	public function setBody(string $body, string $contentType): IMessage {
 		if (!$this->plainTextOnly || $contentType !== 'text/html') {
-			$this->swiftMessage->setBody($body, $contentType);
+			if ($contentType === 'text/html') {
+				$this->symfonyEmail->html($body);
+			} else {
+				$this->symfonyEmail->text($body);
+			}
 		}
 		return $this;
 	}
 
 	/**
-	 * @param IEMailTemplate $emailTemplate
+	 * Set the recipients on the symphony email
+	 *
+	 * Since
+	 *
+	 * setTo
+	 * setFrom
+	 * setReplyTo
+	 * setCc
+	 * setBcc
+	 *
+	 * could throw a \Symfony\Component\Mime\Exception\RfcComplianceException
+	 * or a \Symfony\Component\Mime\Exception\InvalidArgumentException
+	 * we wrap the calls here. We then have the validation errors all in one place and can
+	 * throw shortly before \OC\Mail\Mailer::send
+	 *
+	 * @return void
+	 * @throws InvalidArgumentException|RfcComplianceException
+	 */
+	public function setRecipients() {
+		$this->symfonyEmail->to(...$this->convertAddresses($this->getTo()));
+		$this->symfonyEmail->from(...$this->convertAddresses($this->getFrom()));
+		$this->symfonyEmail->replyTo(...$this->convertAddresses($this->getReplyTo()));
+		$this->symfonyEmail->cc(...$this->convertAddresses($this->getCc()));
+		$this->symfonyEmail->bcc(...$this->convertAddresses($this->getBcc()));
+	}
+
+	/**
 	 * @return $this
 	 */
 	public function useTemplate(IEMailTemplate $emailTemplate): IMessage {
@@ -311,7 +312,7 @@ public function useTemplate(IEMailTemplate $emailTemplate): IMessage {
 	 * @return $this
 	 */
 	public function setAutoSubmitted(string $value): IMessage {
-		$headers = $this->swiftMessage->getHeaders();
+		$headers = $this->symfonyEmail->getHeaders();
 
 		if ($headers->has(AutoSubmitted::HEADER)) {
 			// if the header already exsists, remove it.
@@ -319,6 +320,7 @@ public function setAutoSubmitted(string $value): IMessage {
 			// of the interface \Swift_Mime_Header, however the
 			// interface doesn't, and this makes the static-code
 			// analysis unhappy.
+			// @todo check if symfony mailer can modify the autosubmitted header
 			$headers->remove(AutoSubmitted::HEADER);
 		}
 
@@ -334,9 +336,9 @@ public function setAutoSubmitted(string $value): IMessage {
 	 * @return string
 	 */
 	public function getAutoSubmitted(): string {
-		$headers = $this->swiftMessage->getHeaders();
+		$headers = $this->symfonyEmail->getHeaders();
 
 		return $headers->has(AutoSubmitted::HEADER) ?
-			$headers->get(AutoSubmitted::HEADER)->toString() : AutoSubmitted::VALUE_NO;
+			$headers->get(AutoSubmitted::HEADER)->getBodyAsString() : AutoSubmitted::VALUE_NO;
 	}
 }
diff --git a/lib/public/Mail/IMailer.php b/lib/public/Mail/IMailer.php
index 325abd9301e7b..db46401a3d82b 100644
--- a/lib/public/Mail/IMailer.php
+++ b/lib/public/Mail/IMailer.php
@@ -96,7 +96,7 @@ public function createEMailTemplate(string $emailId, array $data = []): IEMailTe
 	public function send(IMessage $message): array;
 
 	/**
-	 * Checks if an e-mail address is valid
+	 * @deprecated 26.0.0
 	 *
 	 * @param string $email Email address to be validated
 	 * @return bool True if the mail address is valid, false otherwise
diff --git a/tests/lib/Mail/MailerTest.php b/tests/lib/Mail/MailerTest.php
index 74c4f2a62ab85..39e4d689a3709 100644
--- a/tests/lib/Mail/MailerTest.php
+++ b/tests/lib/Mail/MailerTest.php
@@ -22,19 +22,23 @@
 use OCP\L10N\IFactory;
 use OCP\Mail\Events\BeforeMessageSent;
 use Psr\Log\LoggerInterface;
-use Swift_SwiftException;
 use Test\TestCase;
+use PHPUnit\Framework\MockObject\MockObject;
+use Symfony\Component\Mailer\Mailer as SymfonyMailer;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport;
+use Symfony\Component\Mailer\Transport\SendmailTransport;
 
 class MailerTest extends TestCase {
-	/** @var IConfig|\PHPUnit\Framework\MockObject\MockObject */
+	/** @var IConfig|MockObject */
 	private $config;
-	/** @var Defaults|\PHPUnit\Framework\MockObject\MockObject */
+	/** @var Defaults|MockObject */
 	private $defaults;
-	/** @var LoggerInterface|\PHPUnit\Framework\MockObject\MockObject */
+	/** @var LoggerInterface|MockObject */
 	private $logger;
-	/** @var IURLGenerator|\PHPUnit\Framework\MockObject\MockObject */
+	/** @var IURLGenerator|MockObject */
 	private $urlGenerator;
-	/** @var IL10N|\PHPUnit\Framework\MockObject\MockObject */
+	/** @var IL10N|MockObject */
 	private $l10n;
 	/** @var Mailer */
 	private $mailer;
@@ -91,7 +95,7 @@ public function testGetSendmailInstanceSendMail($sendmailMode, $binaryParam) {
 			$path = '/usr/sbin/sendmail';
 		}
 
-		$expected = new \Swift_SendmailTransport($path . $binaryParam);
+		$expected = new SendmailTransport($path . $binaryParam, null, $this->logger);
 		$this->assertEquals($expected, self::invokePrivate($this->mailer, 'getSendMailInstance'));
 	}
 
@@ -109,13 +113,22 @@ public function testGetSendmailInstanceSendMailQmail($sendmailMode, $binaryParam
 				['mail_sendmailmode', 'smtp', $sendmailMode],
 			]);
 
-		$this->assertEquals(new \Swift_SendmailTransport('/var/qmail/bin/sendmail' . $binaryParam), self::invokePrivate($this->mailer, 'getSendMailInstance'));
+		$sendmail = new SendmailTransport('/var/qmail/bin/sendmail' . $binaryParam, null, $this->logger);
+		$this->assertEquals($sendmail, self::invokePrivate($this->mailer, 'getSendMailInstance'));
 	}
 
 	public function testGetInstanceDefault() {
+		$this->config
+			->method('getSystemValue')
+			->willReturnMap([
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+				['mail_smtptimeout', 10, 10],
+			]);
 		$mailer = self::invokePrivate($this->mailer, 'getInstance');
-		$this->assertInstanceOf(\Swift_Mailer::class, $mailer);
-		$this->assertInstanceOf(\Swift_SmtpTransport::class, $mailer->getTransport());
+		$this->assertInstanceOf(SymfonyMailer::class, $mailer);
+		$transport = self::invokePrivate($mailer, 'transport');
+		$this->assertInstanceOf(EsmtpTransport::class, $transport);
 	}
 
 	public function testGetInstanceSendmail() {
@@ -127,11 +140,33 @@ public function testGetInstanceSendmail() {
 			]);
 
 		$mailer = self::invokePrivate($this->mailer, 'getInstance');
-		$this->assertInstanceOf(\Swift_Mailer::class, $mailer);
-		$this->assertInstanceOf(\Swift_SendmailTransport::class, $mailer->getTransport());
+		$this->assertInstanceOf(SymfonyMailer::class, $mailer);
+		$transport = self::invokePrivate($mailer, 'transport');
+		$this->assertInstanceOf(SendmailTransport::class, $transport);
 	}
 
 	public function testEvents() {
+		$this->config
+			->method('getSystemValue')
+			->willReturnMap([
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+			]);
+		$this->mailer = $this->getMockBuilder(Mailer::class)
+			->setMethods(['getInstance'])
+			->setConstructorArgs(
+				[
+					$this->config,
+					$this->logger,
+					$this->defaults,
+					$this->urlGenerator,
+					$this->l10n,
+					$this->dispatcher,
+					$this->createMock(IFactory::class)
+				]
+			)
+			->getMock();
+
 		$message = $this->createMock(Message::class);
 
 		$event = new BeforeMessageSent($message);
@@ -139,11 +174,7 @@ public function testEvents() {
 			->method('dispatchTyped')
 			->with($this->equalTo($event));
 
-		# We do not care at this point about errors in Swiftmailer
-		try {
-			$this->mailer->send($message);
-		} catch (Swift_SwiftException $e) {
-		}
+		$this->mailer->send($message);
 	}
 
 	public function testCreateMessage() {
@@ -157,13 +188,20 @@ public function testCreateMessage() {
 
 
 	public function testSendInvalidMailException() {
+		$this->config
+			->method('getSystemValue')
+			->willReturnMap([
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+				['mail_smtptimeout', 10, 10],
+			]);
 		$this->expectException(\Exception::class);
 
 		$message = $this->getMockBuilder('\OC\Mail\Message')
 			->disableOriginalConstructor()->getMock();
 		$message->expects($this->once())
-			->method('getSwiftMessage')
-			->willReturn(new \Swift_Message());
+			->method('getSymfonyEmail')
+			->willReturn(new Email());
 
 		$this->mailer->send($message);
 	}
@@ -202,58 +240,76 @@ public function testStreamingOptions() {
 		$this->config->method('getSystemValue')
 			->willReturnMap([
 				['mail_smtpmode', 'smtp', 'smtp'],
-				['mail_smtpstreamoptions', [], ['foo' => 1]]
+				['mail_smtpstreamoptions', [], ['foo' => 1]],
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+				['mail_smtptimeout', 10, 10],
 			]);
 		$mailer = self::invokePrivate($this->mailer, 'getInstance');
-		$this->assertEquals(1, count($mailer->getTransport()->getStreamOptions()));
-		$this->assertTrue(isset($mailer->getTransport()->getStreamOptions()['foo']));
+		/** @var EsmtpTransport $transport */
+		$transport = self::invokePrivate($mailer, 'transport');
+		$this->assertInstanceOf(EsmtpTransport::class, $transport);
+		$this->assertEquals(1, count($transport->getStream()->getStreamOptions()));
+		$this->assertTrue(isset($transport->getStream()->getStreamOptions()['foo']));
 	}
 
 	public function testStreamingOptionsWrongType() {
 		$this->config->method('getSystemValue')
 			->willReturnMap([
 				['mail_smtpmode', 'smtp', 'smtp'],
-				['mail_smtpstreamoptions', [], 'bar']
+				['mail_smtpstreamoptions', [], 'bar'],
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+				['mail_smtptimeout', 10, 10],
 			]);
 		$mailer = self::invokePrivate($this->mailer, 'getInstance');
-		$this->assertEquals(0, count($mailer->getTransport()->getStreamOptions()));
+		/** @var EsmtpTransport $transport */
+		$transport = self::invokePrivate($mailer, 'transport');
+		$this->assertInstanceOf(EsmtpTransport::class, $transport);
+		$this->assertEquals(0, count($transport->getStream()->getStreamOptions()));
 	}
 
 	public function testLocalDomain(): void {
 		$this->config->method('getSystemValue')
 			->willReturnMap([
-				['mail_smtpmode', 'smtp', 'smtp']
+				['mail_smtpmode', 'smtp', 'smtp'],
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+				['mail_smtptimeout', 10, 10],
 			]);
 		$this->config->method('getSystemValueString')
 			->with('overwrite.cli.url', '')
 			->willReturn('https://some.valid.url.com:8080');
 
-		/** @var \Swift_Mailer $mailer */
+		/** @var SymfonyMailer $mailer */
 		$mailer = self::invokePrivate($this->mailer, 'getInstance');
-		self::assertInstanceOf(\Swift_Mailer::class, $mailer);
+		self::assertInstanceOf(SymfonyMailer::class, $mailer);
 
-		/** @var \Swift_Transport_EsmtpTransport $transport */
-		$transport = $mailer->getTransport();
-		self::assertInstanceOf(\Swift_Transport_EsmtpTransport::class, $transport);
+		/** @var EsmtpTransport $transport */
+		$transport = self::invokePrivate($mailer, 'transport');
+		self::assertInstanceOf(EsmtpTransport::class, $transport);
 		self::assertEquals('some.valid.url.com', $transport->getLocalDomain());
 	}
 
 	public function testLocalDomainInvalidUrl(): void {
 		$this->config->method('getSystemValue')
 			->willReturnMap([
-				['mail_smtpmode', 'smtp', 'smtp']
+				['mail_smtpmode', 'smtp', 'smtp'],
+				['mail_smtphost', '127.0.0.1', '127.0.0.1'],
+				['mail_smtpport', 25, 25],
+				['mail_smtptimeout', 10, 10],
 			]);
 		$this->config->method('getSystemValueString')
 			->with('overwrite.cli.url', '')
 			->willReturn('https:only.slash.does.not.work:8080');
 
-		/** @var \Swift_Mailer $mailer */
+		/** @var SymfonyMailer $mailer */
 		$mailer = self::invokePrivate($this->mailer, 'getInstance');
-		self::assertInstanceOf(\Swift_Mailer::class, $mailer);
+		self::assertInstanceOf(SymfonyMailer::class, $mailer);
 
-		/** @var \Swift_Transport_EsmtpTransport $transport */
-		$transport = $mailer->getTransport();
-		self::assertInstanceOf(\Swift_Transport_EsmtpTransport::class, $transport);
+		/** @var EsmtpTransport $transport */
+		$transport = self::invokePrivate($mailer, 'transport');
+		self::assertInstanceOf(EsmtpTransport::class, $transport);
 		self::assertEquals('[127.0.0.1]', $transport->getLocalDomain());
 	}
 }
diff --git a/tests/lib/Mail/MessageTest.php b/tests/lib/Mail/MessageTest.php
index b97240d13366d..2becc4d2081a7 100644
--- a/tests/lib/Mail/MessageTest.php
+++ b/tests/lib/Mail/MessageTest.php
@@ -11,12 +11,17 @@
 use OC\Mail\Message;
 use OCP\Mail\Headers\AutoSubmitted;
 use OCP\Mail\IEMailTemplate;
-use Swift_Message;
+use Symfony\Component\Mime\Address;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mime\Exception\RfcComplianceException;
+use Symfony\Component\Mime\Header\HeaderInterface;
+use Symfony\Component\Mime\Header\Headers;
 use Test\TestCase;
+use PHPUnit\Framework\MockObject\MockObject;
 
 class MessageTest extends TestCase {
-	/** @var Swift_Message */
-	private $swiftMessage;
+	/** @var Email */
+	private $symfonyEmail;
 	/** @var Message */
 	private $message;
 
@@ -25,10 +30,26 @@ class MessageTest extends TestCase {
 	 */
 	public function mailAddressProvider() {
 		return [
-			[['lukas@owncloud.com' => 'Lukas Reschke'], ['lukas@owncloud.com' => 'Lukas Reschke']],
-			[['lukas@owncloud.com' => 'Lukas Reschke', 'lukas@öwnclöüd.com', 'lukäs@owncloud.örg' => 'Lükäs Réschke'],
-				['lukas@owncloud.com' => 'Lukas Reschke', 'lukas@xn--wncld-iuae2c.com', 'lukäs@owncloud.xn--rg-eka' => 'Lükäs Réschke']],
-			[['lukas@öwnclöüd.com'], ['lukas@xn--wncld-iuae2c.com']],
+			[
+				['lukas@owncloud.com' => 'Lukas Reschke'],
+				[new Address('lukas@owncloud.com', 'Lukas Reschke')]
+			],
+			[
+				[
+					'lukas@owncloud.com' => 'Lukas Reschke',
+					'lukas@öwnclöüd.com',
+					'lukäs@owncloud.örg' => 'Lükäs Réschke'
+				],
+				[
+					new Address('lukas@owncloud.com', 'Lukas Reschke'),
+					new Address('lukas@öwnclöüd.com'),
+					new Address('lukäs@owncloud.örg', 'Lükäs Réschke')
+				]
+			],
+			[
+				['lukas@öwnclöüd.com'],
+				[new Address('lukas@öwnclöüd.com')]
+			],
 		];
 	}
 
@@ -37,7 +58,7 @@ public function mailAddressProvider() {
 	 */
 	public function getMailAddressProvider() {
 		return [
-			[null, []],
+			[[], []],
 			[['lukas@owncloud.com' => 'Lukas Reschke'], ['lukas@owncloud.com' => 'Lukas Reschke']],
 		];
 	}
@@ -45,189 +66,158 @@ public function getMailAddressProvider() {
 	protected function setUp(): void {
 		parent::setUp();
 
-		$this->swiftMessage = $this->getMockBuilder('\Swift_Message')
+		$this->symfonyEmail = $this->getMockBuilder(Email::class)
 			->disableOriginalConstructor()->getMock();
 
-		$this->message = new Message($this->swiftMessage, false);
+		$this->message = new Message($this->symfonyEmail, false);
 	}
 
 	/**
-	 * @requires function idn_to_ascii
 	 * @dataProvider mailAddressProvider
 	 *
 	 * @param string $unconverted
 	 * @param string $expected
 	 */
 	public function testConvertAddresses($unconverted, $expected) {
-		$this->assertSame($expected, self::invokePrivate($this->message, 'convertAddresses', [$unconverted]));
-	}
-
-	public function testSetFrom() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('setFrom')
-			->with(['lukas@owncloud.com']);
-		$this->message->setFrom(['lukas@owncloud.com']);
+		$this->assertEquals($expected, self::invokePrivate($this->message, 'convertAddresses', [$unconverted]));
 	}
 
+	public function testSetRecipients(): void {
+		$this->message = $this->message->setFrom(['pierres-general-store@stardewvalley.com' => 'Pierres General Store']);
+		$this->message = $this->message->setTo(['lewis-tent@stardewvalley.com' => "Lewis' Tent Life"]);
+		$this->message = $this->message->setReplyTo(['penny@stardewvalley-library.co.edu' => 'Penny']);
+		$this->message = $this->message->setCc(['gunther@stardewvalley-library.co.edu' => 'Gunther']);
+		$this->message = $this->message->setBcc(['pam@stardewvalley-bus.com' => 'Pam']);
 
-	/**
-	 * @dataProvider getMailAddressProvider
-	 *
-	 * @param $swiftresult
-	 * @param $return
-	 */
-	public function testGetFrom($swiftresult, $return) {
-		$this->swiftMessage
+		$this->symfonyEmail
+			->expects($this->once())
+			->method('from')
+			->willReturn(new Address('pierres-general-store@stardewvalley.com', 'Pierres General Store'));
+		$this->symfonyEmail
+			->expects($this->once())
+			->method('to')
+			->willReturn(new Address('lewis-tent@stardewvalley.com', "Lewis' Tent Life"));
+		$this->symfonyEmail
+			->expects($this->once())
+			->method('replyTo')
+			->willReturn(new Address('penny@stardewvalley-library.co.edu', 'Penny'));
+		$this->symfonyEmail
+			->expects($this->once())
+			->method('cc')
+			->willReturn(new Address('gunther@stardewvalley-library.co.edu', 'Gunther'));
+		$this->symfonyEmail
 			->expects($this->once())
-			->method('getFrom')
-			->willReturn($swiftresult);
+			->method('bcc')
+			->willReturn(new Address('pam@stardewvalley-bus.com', 'Pam'));
 
-		$this->assertSame($return, $this->message->getFrom());
+		$this->message->setRecipients();
 	}
 
-	public function testSetReplyTo() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('setReplyTo')
-			->with(['lukas@owncloud.com']);
-		$this->message->setReplyTo(['lukas@owncloud.com']);
-	}
+	public function testSetTo() {
+		$expected = ['pierres-general-store@stardewvalley.com' => 'Pierres General Store'];
 
-	public function testGetReplyTo() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('getReplyTo')
-			->willReturn('lukas@owncloud.com');
+		$message = $this->message->setTo(['pierres-general-store@stardewvalley.com' => 'Pierres General Store']);
 
-		$this->assertSame('lukas@owncloud.com', $this->message->getReplyTo());
+		$this->assertEquals($expected, $message->getTo());
 	}
+	public function testSetRecipientsException(): void {
+		$message = $this->message->setTo(['lewis-tent@~~~~.com' => "Lewis' Tent Life"]);
 
-	/** @dataProvider dataSetTo */
-	public function testSetTo(array $to, array $expected) {
-		$this->swiftMessage
+		$this->symfonyEmail
 			->expects($this->once())
-			->method('setTo')
-			->with($expected);
-		$this->message->setTo($to);
-	}
+			->method('to')
+			->willThrowException(new RfcComplianceException());
 
-	public function dataSetTo(): array {
-		return [
-			[['robot@example.com'], ['robot@example.com']],
-			[['robot'], ['robot' => 'robot']],
-			[['robot' => 'robot display name'], ['robot' => 'robot display name']],
-			[['example@🤖.com'], ['example@xn--yp9h.com']],
-			[['example@🤖.com' => 'A robot'], ['example@xn--yp9h.com' => 'A robot']],
-		];
+		$this->expectException(RfcComplianceException::class);
+		$message->setRecipients();
 	}
 
-	/**
-	 * @dataProvider  getMailAddressProvider
-	 */
-	public function testGetTo($swiftresult, $return) {
-		$this->swiftMessage
+	public function testSetRecipientsEmptyValues(): void {
+		$message = $this->message->setTo([]);
+
+		$this->symfonyEmail
 			->expects($this->once())
-			->method('getTo')
-			->willReturn($swiftresult);
+			->method('to');
 
-		$this->assertSame($return, $this->message->getTo());
+		$message->setRecipients();
 	}
 
-	public function testSetCc() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('setCc')
-			->with(['lukas@owncloud.com']);
-		$this->message->setCc(['lukas@owncloud.com']);
-	}
+	public function testSetGetFrom() {
+		$expected = ['pierres-general-store@stardewvalley.com' => 'Pierres General Store'];
 
-	/**
-	 * @dataProvider  getMailAddressProvider
-	 */
-	public function testGetCc($swiftresult, $return) {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('getCc')
-			->willReturn($swiftresult);
+		$message = $this->message->setFrom(['pierres-general-store@stardewvalley.com' => 'Pierres General Store']);
 
-		$this->assertSame($return, $this->message->getCc());
+		$this->assertEquals($expected, $message->getFrom());
 	}
 
-	public function testSetBcc() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('setBcc')
-			->with(['lukas@owncloud.com']);
-		$this->message->setBcc(['lukas@owncloud.com']);
+	public function testSetGetTo() {
+		$expected = ['lewis-tent@stardewvalley.com' => "Lewis' Tent Life"];
+
+		$message = $this->message->setTo(['lewis-tent@stardewvalley.com' => "Lewis' Tent Life"]);
+
+		$this->assertEquals($expected, $message->getTo());
 	}
 
-	/**
-	 * @dataProvider  getMailAddressProvider
-	 */
-	public function testGetBcc($swiftresult, $return) {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('getBcc')
-			->willReturn($swiftresult);
+	public function testSetGetReplyTo() {
+		$expected = ['penny@stardewvalley-library.co.edu' => 'Penny'];
 
-		$this->assertSame($return, $this->message->getBcc());
+		$message = $this->message->setReplyTo(['penny@stardewvalley-library.co.edu' => 'Penny']);
+
+		$this->assertEquals($expected, $message->getReplyTo());
 	}
 
-	public function testSetSubject() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('setSubject')
-			->with('Fancy Subject');
+	public function testSetGetCC() {
+		$expected = ['gunther@stardewvalley-library.co.edu' => 'Gunther'];
 
-		$this->message->setSubject('Fancy Subject');
+		$message = $this->message->setCc(['gunther@stardewvalley-library.co.edu' => 'Gunther']);
+
+		$this->assertEquals($expected, $message->getCc());
 	}
 
-	public function testGetSubject() {
-		$this->swiftMessage
-			->expects($this->once())
-			->method('getSubject')
-			->willReturn('Fancy Subject');
+	public function testSetGetBCC() {
+		$expected = ['pam@stardewvalley-bus.com' => 'Pam'];
+
+		$message = $this->message->setBcc(['pam@stardewvalley-bus.com' => 'Pam']);
 
-		$this->assertSame('Fancy Subject', $this->message->getSubject());
+		$this->assertEquals($expected, $message->getBcc());
 	}
 
 	public function testSetPlainBody() {
-		$this->swiftMessage
+		$this->symfonyEmail
 			->expects($this->once())
-			->method('setBody')
+			->method('text')
 			->with('Fancy Body');
 
 		$this->message->setPlainBody('Fancy Body');
 	}
 
 	public function testGetPlainBody() {
-		$this->swiftMessage
+		$this->symfonyEmail
 			->expects($this->once())
-			->method('getBody')
+			->method('getTextBody')
 			->willReturn('Fancy Body');
 
 		$this->assertSame('Fancy Body', $this->message->getPlainBody());
 	}
 
 	public function testSetHtmlBody() {
-		$this->swiftMessage
+		$this->symfonyEmail
 			->expects($this->once())
-			->method('addPart')
-			->with('<blink>Fancy Body</blink>', 'text/html');
+			->method('html')
+			->with('<blink>Fancy Body</blink>', 'utf-8');
 
 		$this->message->setHtmlBody('<blink>Fancy Body</blink>');
 	}
 
 	public function testPlainTextRenderOption() {
-		/** @var \PHPUnit\Framework\MockObject\MockObject|Swift_Message $swiftMessage */
-		$swiftMessage = $this->getMockBuilder('\Swift_Message')
+		/** @var MockObject|Email $symfonyEmail */
+		$symfonyEmail = $this->getMockBuilder(Email::class)
 			->disableOriginalConstructor()->getMock();
-		/** @var \PHPUnit\Framework\MockObject\MockObject|IEMailTemplate $template */
-		$template = $this->getMockBuilder('\OCP\Mail\IEMailTemplate')
+		/** @var MockObject|IEMailTemplate $template */
+		$template = $this->getMockBuilder(IEMailTemplate::class)
 			->disableOriginalConstructor()->getMock();
 
-		$message = new Message($swiftMessage, true);
+		$message = new Message($symfonyEmail, true);
 
 		$template
 			->expects($this->never())
@@ -243,14 +233,14 @@ public function testPlainTextRenderOption() {
 	}
 
 	public function testBothRenderingOptions() {
-		/** @var \PHPUnit\Framework\MockObject\MockObject|Swift_Message $swiftMessage */
-		$swiftMessage = $this->getMockBuilder('\Swift_Message')
+		/** @var MockObject|Email $symfonyEmail */
+		$symfonyEmail = $this->getMockBuilder(Email::class)
 			->disableOriginalConstructor()->getMock();
-		/** @var \PHPUnit\Framework\MockObject\MockObject|IEMailTemplate $template */
-		$template = $this->getMockBuilder('\OCP\Mail\IEMailTemplate')
+		/** @var MockObject|IEMailTemplate $template */
+		$template = $this->getMockBuilder(IEMailTemplate::class)
 			->disableOriginalConstructor()->getMock();
 
-		$message = new Message($swiftMessage, false);
+		$message = new Message($symfonyEmail, false);
 
 		$template
 			->expects($this->once())
@@ -266,108 +256,40 @@ public function testBothRenderingOptions() {
 	}
 
 	public function testSetAutoSubmitted1() {
-		$swiftMimeSimpleHeaderSet = $this->getMockBuilder('\Swift_Mime_SimpleHeaderSet')
-			->disableOriginalConstructor()
-			->getMock();
-		$swiftMessage = $this->getMockBuilder('\Swift_Message')
-			->disableOriginalConstructor()
-			->disableOriginalClone()
-			->disableArgumentCloning()
-			->disallowMockingUnknownTypes()
-			->getMock();
-
-		$swiftMessage->method('getHeaders')->willReturn($swiftMimeSimpleHeaderSet);
-
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('has')
-			->with('Auto-Submitted');
-		$swiftMimeSimpleHeaderSet->expects($this->never())
-			->method('remove');
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('addTextHeader')
-			->with('Auto-Submitted', AutoSubmitted::VALUE_AUTO_GENERATED);
-
-		$message = new Message($swiftMessage, false);
+		$headers = new Headers($this->createMock(HeaderInterface::class));
+		$headers->addTextHeader(AutoSubmitted::HEADER, "yes");
+		$symfonyEmail = $this->createMock(Email::class);
+
+		$symfonyEmail->method('getHeaders')
+			->willReturn($headers);
+
+		$message = new Message($symfonyEmail, false);
 		$message->setAutoSubmitted(AutoSubmitted::VALUE_AUTO_GENERATED);
+		$this->assertNotSame('no', $message->getAutoSubmitted());
 	}
 
 	public function testSetAutoSubmitted2() {
-		$swiftMimeSimpleHeaderSet = $this->getMockBuilder('\Swift_Mime_SimpleHeaderSet')
-			->disableOriginalConstructor()
-			->getMock();
-		$swiftMessage = $this->getMockBuilder('\Swift_Message')
-			->disableOriginalConstructor()
-			->disableOriginalClone()
-			->disableArgumentCloning()
-			->disallowMockingUnknownTypes()
-			->getMock();
-
-		$swiftMessage->method('getHeaders')->willReturn($swiftMimeSimpleHeaderSet);
-
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('has')
-			->with('Auto-Submitted')
-			->willReturn(true);
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('remove')
-			->with('Auto-Submitted');
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('addTextHeader')
-			->with('Auto-Submitted', AutoSubmitted::VALUE_AUTO_GENERATED);
-
-		$message = new Message($swiftMessage, false);
+		$headers = new Headers($this->createMock(HeaderInterface::class));
+		$headers->addTextHeader(AutoSubmitted::HEADER, 'no');
+		$symfonyEmail = $this->createMock(Email::class);
+
+		$symfonyEmail->method('getHeaders')
+			->willReturn($headers);
+
+		$message = new Message($symfonyEmail, false);
 		$message->setAutoSubmitted(AutoSubmitted::VALUE_AUTO_GENERATED);
+		$this->assertSame('auto-generated', $message->getAutoSubmitted());
 	}
 
-	public function testGetAutoSubmitted1() {
-		$swiftMimeSimpleHeaderSet = $this->getMockBuilder('\Swift_Mime_SimpleHeaderSet')
-			->disableOriginalConstructor()
-			->getMock();
-		$swiftMessage = $this->getMockBuilder('\Swift_Message')
-			->disableOriginalConstructor()
-			->disableOriginalClone()
-			->disableArgumentCloning()
-			->disallowMockingUnknownTypes()
-			->getMock();
-
-		$swiftMessage->method('getHeaders')->willReturn($swiftMimeSimpleHeaderSet);
-
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('has')
-			->with('Auto-Submitted');
-		$swiftMimeSimpleHeaderSet->expects($this->never())
-			->method('get');
-
-		$message = new Message($swiftMessage, false);
+	public function testGetAutoSubmitted() {
+		$headers = new Headers($this->createMock(HeaderInterface::class));
+		$headers->addTextHeader(AutoSubmitted::HEADER, 'no');
+		$symfonyEmail = $this->createMock(Email::class);
+
+		$symfonyEmail->method('getHeaders')
+			->willReturn($headers);
+
+		$message = new Message($symfonyEmail, false);
 		$this->assertSame("no", $message->getAutoSubmitted());
 	}
-	public function testGetAutoSubmitted2() {
-		$swiftMimeHeader = $this->getMockBuilder('\Swift_Mime_Header')
-			->disableOriginalConstructor()
-			->getMockForAbstractClass();
-		$swiftMimeSimpleHeaderSet = $this->getMockBuilder('\Swift_Mime_SimpleHeaderSet')
-			->disableOriginalConstructor()
-			->getMock();
-		$swiftMessage = $this->getMockBuilder('\Swift_Message')
-			->disableOriginalConstructor()
-			->disableOriginalClone()
-			->disableArgumentCloning()
-			->disallowMockingUnknownTypes()
-			->getMock();
-
-
-		$swiftMessage->method('getHeaders')->willReturn($swiftMimeSimpleHeaderSet);
-		$swiftMimeHeader->method('toString')->willReturn(AutoSubmitted::VALUE_AUTO_GENERATED);
-
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('has')
-			->with('Auto-Submitted')
-			->willReturn(true);
-		$swiftMimeSimpleHeaderSet->expects($this->once())
-			->method('get')
-			->willReturn($swiftMimeHeader);
-
-		$message = new Message($swiftMessage, false);
-		$this->assertSame(AutoSubmitted::VALUE_AUTO_GENERATED, $message->getAutoSubmitted());
-	}
 }

From e123d270fcf099d780d8b35f9b7000c28b02fd5d Mon Sep 17 00:00:00 2001
From: Arthur Schiwon <blizzz@arthur-schiwon.de>
Date: Thu, 2 Feb 2023 10:17:42 +0100
Subject: [PATCH 2/2] remove depraction of validateEmailAddress

for there are legit use cases to validate an email address without
sending there to

Signed-off-by: Arthur Schiwon <blizzz@arthur-schiwon.de>
---
 lib/public/Mail/IMailer.php | 2 --
 1 file changed, 2 deletions(-)

diff --git a/lib/public/Mail/IMailer.php b/lib/public/Mail/IMailer.php
index db46401a3d82b..94044f7c72093 100644
--- a/lib/public/Mail/IMailer.php
+++ b/lib/public/Mail/IMailer.php
@@ -96,8 +96,6 @@ public function createEMailTemplate(string $emailId, array $data = []): IEMailTe
 	public function send(IMessage $message): array;
 
 	/**
-	 * @deprecated 26.0.0
-	 *
 	 * @param string $email Email address to be validated
 	 * @return bool True if the mail address is valid, false otherwise
 	 * @since 8.1.0