Local Draft Handling Backend

Signed-off-by: Anna Larch <anna@nextcloud.com>

13 files changed, 1188 insertions, 13 deletions

diff --git a/appinfo/info.xml b/appinfo/info.xml
index 051395a95..93e91dc9c 100644
--- a/appinfo/info.xml
+++ b/appinfo/info.xml
@@ -12,7 +12,7 @@
 - **🙈 We’re not reinventing the wheel!** Based on the great [Horde](https://horde.org) libraries.
 - **📬 Want to host your own mail server?** We do not have to reimplement this as you could set up [Mail-in-a-Box](https://mailinabox.email)!
 	]]></description>
-	<version>2.2.0-alpha.0</version>
+	<version>2.2.0-alpha.1</version>
 	<licence>agpl</licence>
 	<author>Greta Doçi</author>
 	<author homepage="https://github.com/nextcloud/groupware">Nextcloud Groupware Team</author>
diff --git a/lib/AppInfo/Application.php b/lib/AppInfo/Application.php
index 0cae71c6b..106e7b65b 100644
--- a/lib/AppInfo/Application.php
+++ b/lib/AppInfo/Application.php
@@ -35,6 +35,7 @@ use OCA\Mail\Contracts\IUserPreferences;
 use OCA\Mail\Dashboard\ImportantMailWidget;
 use OCA\Mail\Dashboard\UnreadMailWidget;
 use OCA\Mail\Events\BeforeMessageSentEvent;
+use OCA\Mail\Events\DraftMessageCreatedEvent;
 use OCA\Mail\Events\DraftSavedEvent;
 use OCA\Mail\Events\MailboxesSynchronizedEvent;
 use OCA\Mail\Events\OutboxMessageCreatedEvent;
@@ -105,6 +106,7 @@ class Application extends App implements IBootstrap {
 
 		$context->registerEventListener(BeforeMessageSentEvent::class, AntiAbuseListener::class);
 		$context->registerEventListener(DraftSavedEvent::class, DeleteDraftListener::class);
+		$context->registerEventListener(DraftMessageCreatedEvent::class, DeleteDraftListener::class);
 		$context->registerEventListener(OutboxMessageCreatedEvent::class, DeleteDraftListener::class);
 		$context->registerEventListener(MailboxesSynchronizedEvent::class, MailboxesSynchronizedSpecialMailboxesUpdater::class);
 		$context->registerEventListener(MessageFlaggedEvent::class, MessageCacheUpdaterListener::class);
diff --git a/lib/BackgroundJob/DraftsJob.php b/lib/BackgroundJob/DraftsJob.php
new file mode 100644
index 000000000..1bd5f0627
--- /dev/null
+++ b/lib/BackgroundJob/DraftsJob.php
@@ -0,0 +1,57 @@
+<?php
+
+declare(strict_types=1);
+
+/*
+ * @copyright 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @author 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @license GNU AGPL version 3 or any later version
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as
+ * published by the Free Software Foundation, either version 3 of the
+ * License, or (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ */
+
+namespace OCA\Mail\BackgroundJob;
+
+use OCA\Mail\Db\LocalMessageMapper;
+use OCA\Mail\Service\AccountService;
+use OCA\Mail\Service\DraftsService;
+use OCP\AppFramework\Utility\ITimeFactory;
+use OCP\BackgroundJob\TimedJob;
+use Psr\Log\LoggerInterface;
+
+class DraftsJob extends TimedJob {
+	private DraftsService $draftsService;
+	private LocalMessageMapper $messageMapper;
+	private AccountService $accountService;
+	private LoggerInterface $logger;
+
+	public function __construct(ITimeFactory $time,
+								DraftsService $draftsService,
+								AccountService $accountService,
+								LocalMessageMapper $messageMapper,
+								LoggerInterface $logger) {
+		parent::__construct($time);
+
+		// Run once per five minutes
+		$this->setInterval(5 * 60);
+		$this->setTimeSensitivity(self::TIME_SENSITIVE);
+		$this->draftsService = $draftsService;
+	}
+
+	protected function run($argument): void {
+		$this->draftsService->flush();
+	}
+}
diff --git a/lib/Contracts/IMailTransmission.php b/lib/Contracts/IMailTransmission.php
index f8e29bbd9..812c921fc 100644
--- a/lib/Contracts/IMailTransmission.php
+++ b/lib/Contracts/IMailTransmission.php
@@ -57,7 +57,7 @@ interface IMailTransmission {
 	 * @throws ServiceException
 	 * @return void
 	 */
-	public function sendLocalMessage(Account $account, LocalMessage $message): void;
+	public function sendLocalMessage(Account $account, LocalMessage $message, bool $isDraft = false): void;
 
 	/**
 	 * Save a message draft
diff --git a/lib/Controller/DraftsController.php b/lib/Controller/DraftsController.php
new file mode 100644
index 000000000..b008ea117
--- /dev/null
+++ b/lib/Controller/DraftsController.php
@@ -0,0 +1,198 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * Mail App
+ *
+ * @copyright 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @author Anna Larch <anna.larch@gmx.net>
+ *
+ * This library is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU AFFERO GENERAL PUBLIC LICENSE
+ * License as published by the Free Software Foundation; either
+ * version 3 of the License, or any later version.
+ *
+ * This library is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU AFFERO GENERAL PUBLIC LICENSE for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public
+ * License along with this library.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ */
+
+namespace OCA\Mail\Controller;
+
+use OCA\Mail\Db\LocalMessage;
+use OCA\Mail\Http\JsonResponse;
+use OCA\Mail\Service\AccountService;
+use OCA\Mail\Service\DraftsService;
+use OCP\AppFramework\Controller;
+use OCP\AppFramework\Http;
+use OCP\AppFramework\Utility\ITimeFactory;
+use OCP\IRequest;
+
+class DraftsController extends Controller {
+	private DraftsService $service;
+	private string $userId;
+	private AccountService $accountService;
+	private ITimeFactory $timeFactory;
+
+	public function __construct(string $appName,
+								$UserId,
+								IRequest $request,
+								DraftsService $service,
+								AccountService $accountService,
+								ITimeFactory $timeFactory) {
+		parent::__construct($appName, $request);
+		$this->userId = $UserId;
+		$this->service = $service;
+		$this->accountService = $accountService;
+		$this->timeFactory = $timeFactory;
+	}
+
+	/**
+	 * @NoAdminRequired
+	 * @TrapError
+	 *
+	 * @param int $accountId
+	 * @param string $subject
+	 * @param string $body
+	 * @param string $editorBody
+	 * @param bool $isHtml
+	 * @param array $to i. e. [['label' => 'Linus', 'email' => 'tent@stardewvalley.com'], ['label' => 'Pierre', 'email' => 'generalstore@stardewvalley.com']]
+	 * @param array $cc
+	 * @param array $bcc
+	 * @param array $attachments
+	 * @param int|null $aliasId
+	 * @param string|null $inReplyToMessageId
+	 * @param int|null $sendAt
+	 * @param int|null $draftId
+	 * @return JsonResponse
+	 */
+	public function create(
+		int     $accountId,
+		string  $subject,
+		string  $body,
+		string  $editorBody,
+		bool    $isHtml,
+		array   $to = [],
+		array   $cc = [],
+		array   $bcc = [],
+		array   $attachments = [],
+		?int    $aliasId = null,
+		?string $inReplyToMessageId = null,
+		?int $sendAt = null,
+		?int $draftId = null) : JsonResponse {
+		$account = $this->accountService->find($this->userId, $accountId);
+		if ($draftId !== null) {
+			$this->service->handleDraft($account, $draftId);
+		}
+		$message = new LocalMessage();
+		$message->setType(LocalMessage::TYPE_DRAFT);
+		$message->setAccountId($accountId);
+		$message->setAliasId($aliasId);
+		$message->setSubject($subject);
+		$message->setBody($body);
+		$message->setEditorBody($editorBody);
+		$message->setHtml($isHtml);
+		$message->setInReplyToMessageId($inReplyToMessageId);
+		$message->setUpdatedAt($this->timeFactory->getTime());
+		$message->setSendAt($sendAt);
+		if ($sendAt !== null) {
+			$message->setType(LocalMessage::TYPE_OUTGOING);
+		}
+		$this->service->saveMessage($account, $message, $to, $cc, $bcc, $attachments);
+
+		return JsonResponse::success($message, Http::STATUS_CREATED);
+	}
+
+	/**
+	 * @NoAdminRequired
+	 * @TrapError
+	 *
+	 * @param int $id
+	 * @param int $accountId
+	 * @param string $subject
+	 * @param string $body
+	 * @param string $editorBody
+	 * @param bool $isHtml
+	 * @param bool $failed
+	 * @param array $to i. e. [['label' => 'Linus', 'email' => 'tent@stardewvalley.com'], ['label' => 'Pierre', 'email' => 'generalstore@stardewvalley.com']]
+	 * @param array $cc
+	 * @param array $bcc
+	 * @param array $attachments
+	 * @param int|null $aliasId
+	 * @param string|null $inReplyToMessageId
+	 * @param int|null $sendAt
+	 * @return JsonResponse
+	 */
+	public function update(int $id,
+		int     $accountId,
+		string  $subject,
+		string  $body,
+		string  $editorBody,
+		bool    $isHtml,
+		bool    $failed = false,
+		array   $to = [],
+		array   $cc = [],
+		array   $bcc = [],
+		array   $attachments = [],
+		?int    $aliasId = null,
+		?string $inReplyToMessageId = null,
+		?int $sendAt = null): JsonResponse {
+		$message = $this->service->getMessage($id, $this->userId);
+		$account = $this->accountService->find($this->userId, $accountId);
+
+		($sendAt !== null)
+			? $message->setType(LocalMessage::TYPE_OUTGOING)
+			: $message->setType(LocalMessage::TYPE_DRAFT);
+		$message->setAccountId($accountId);
+		$message->setAliasId($aliasId);
+		$message->setSubject($subject);
+		$message->setBody($body);
+		$message->setEditorBody($editorBody);
+		$message->setHtml($isHtml);
+		$message->setFailed($failed);
+		$message->setInReplyToMessageId($inReplyToMessageId);
+		$message->setSendAt($sendAt);
+		$message->setUpdatedAt($this->timeFactory->getTime());
+
+		$message = $this->service->updateMessage($account, $message, $to, $cc, $bcc, $attachments);
+		return JsonResponse::success($message, Http::STATUS_ACCEPTED);
+	}
+
+	/**
+	 * @NoAdminRequired
+	 * @TrapError
+	 *
+	 * @param int $id
+	 * @return JsonResponse
+	 */
+	public function destroy(int $id): JsonResponse {
+		$message = $this->service->getMessage($id, $this->userId);
+		$account = $this->accountService->find($this->userId, $message->getAccountId());
+
+		$this->service->deleteMessage($this->userId, $message);
+		return JsonResponse::success('Message deleted', Http::STATUS_ACCEPTED);
+	}
+
+	/**
+	 * @NoAdminRequired
+	 * @TrapError
+	 * @param int $id
+	 * @return JsonResponse
+	 */
+	public function move(int $id): JsonResponse {
+		$message = $this->service->getMessage($id, $this->userId);
+		$account = $this->accountService->find($this->userId, $message->getAccountId());
+
+		$this->service->sendMessage($message, $account);
+		return  JsonResponse::success(
+			'Message moved to IMAP', Http::STATUS_ACCEPTED
+		);
+	}
+}
diff --git a/lib/Db/LocalMessage.php b/lib/Db/LocalMessage.php
index 944b403f9..4e1b72ad0 100644
--- a/lib/Db/LocalMessage.php
+++ b/lib/Db/LocalMessage.php
@@ -37,8 +37,8 @@ use function array_filter;
  * @method void setAccountId(int $accountId)
  * @method int|null getAliasId()
  * @method void setAliasId(?int $aliasId)
- * @method int getSendAt()
- * @method void setSendAt(int $sendAt)
+ * @method int|null getSendAt()
+ * @method void setSendAt(?int $sendAt)
  * @method string getSubject()
  * @method void setSubject(string $subject)
  * @method string getBody()
@@ -51,6 +51,8 @@ use function array_filter;
  * @method void setFailed(bool $failed)
  * @method string|null getInReplyToMessageId()
  * @method void setInReplyToMessageId(?string $inReplyToId)
+ * @method int|null getUpdatedAt()
+ * @method setUpdatedAt(?int $updatedAt)
  */
 class LocalMessage extends Entity implements JsonSerializable {
 	public const TYPE_OUTGOING = 0;
@@ -95,6 +97,9 @@ class LocalMessage extends Entity implements JsonSerializable {
 	/** @var bool|null */
 	protected $failed;
 
+	/** @var int|null */
+	protected $updatedAt;
+
 	public function __construct() {
 		$this->addType('type', 'integer');
 		$this->addType('accountId', 'integer');
@@ -102,6 +107,7 @@ class LocalMessage extends Entity implements JsonSerializable {
 		$this->addType('sendAt', 'integer');
 		$this->addType('html', 'boolean');
 		$this->addType('failed', 'boolean');
+		$this->addType('updatedAt', 'integer');
 	}
 
 	#[ReturnTypeWillChange]
@@ -112,6 +118,7 @@ class LocalMessage extends Entity implements JsonSerializable {
 			'accountId' => $this->getAccountId(),
 			'aliasId' => $this->getAliasId(),
 			'sendAt' => $this->getSendAt(),
+			'updatedAt' => $this->getUpdatedAt(),
 			'subject' => $this->getSubject(),
 			'body' => $this->getBody(),
 			'editorBody' => $this->getEditorBody(),
diff --git a/lib/Db/LocalMessageMapper.php b/lib/Db/LocalMessageMapper.php
index b15b917fe..7a2e2801d 100644
--- a/lib/Db/LocalMessageMapper.php
+++ b/lib/Db/LocalMessageMapper.php
@@ -57,14 +57,14 @@ class LocalMessageMapper extends QBMapper {
 	 * @return LocalMessage[]
 	 * @throws DBException
 	 */
-	public function getAllForUser(string $userId): array {
+	public function getAllForUser(string $userId, int $type = LocalMessage::TYPE_OUTGOING): array {
 		$qb = $this->db->getQueryBuilder();
 		$qb->select('m.*')
 			->from('mail_accounts', 'a')
 			->join('a', $this->getTableName(), 'm', $qb->expr()->eq('m.account_id', 'a.id'))
 			->where(
 				$qb->expr()->eq('a.user_id', $qb->createNamedParameter($userId, IQueryBuilder::PARAM_STR), IQueryBuilder::PARAM_STR),
-				$qb->expr()->eq('m.type', $qb->createNamedParameter(LocalMessage::TYPE_OUTGOING, IQueryBuilder::PARAM_INT), IQueryBuilder::PARAM_INT)
+				$qb->expr()->eq('m.type', $qb->createNamedParameter($type, IQueryBuilder::PARAM_INT), IQueryBuilder::PARAM_INT)
 			);
 		$rows = $qb->execute();
 
@@ -124,12 +124,13 @@ class LocalMessageMapper extends QBMapper {
 	 *
 	 * @return LocalMessage[]
 	 */
-	public function findDue(int $time): array {
+	public function findDue(int $time, int $type = LocalMessage::TYPE_OUTGOING): array {
 		$qb = $this->db->getQueryBuilder();
 		$select = $qb->select('*')
 			->from($this->getTableName())
 			->where(
 				$qb->expr()->isNotNull('send_at'),
+				$qb->expr()->eq('type', $qb->createNamedParameter($type, IQueryBuilder::PARAM_INT), IQueryBuilder::PARAM_INT),
 				$qb->expr()->lte('send_at', $qb->createNamedParameter($time, IQueryBuilder::PARAM_INT), IQueryBuilder::PARAM_INT),
 				$qb->expr()->orX(
 					$qb->expr()->isNull('failed'),
@@ -167,6 +168,57 @@ class LocalMessageMapper extends QBMapper {
 	}
 
 	/**
+	 * Find all messages that should be sent
+	 *
+	 * @param int $time upper bound send time stamp
+	 *
+	 * @return LocalMessage[]
+	 */
+	public function findDueDrafts(int $time): array {
+		$qb = $this->db->getQueryBuilder();
+		$select = $qb->select('*')
+			->from($this->getTableName())
+			->where(
+				$qb->expr()->isNotNull('send_at'),
+				$qb->expr()->eq('type', $qb->createNamedParameter(LocalMessage::TYPE_DRAFT, IQueryBuilder::PARAM_INT), IQueryBuilder::PARAM_INT),
+				$qb->expr()->lte('updated_at', $qb->createNamedParameter($time - 300, IQueryBuilder::PARAM_INT), IQueryBuilder::PARAM_INT),
+				$qb->expr()->orX(
+					$qb->expr()->isNull('failed'),
+					$qb->expr()->eq('failed', $qb->createNamedParameter(false, IQueryBuilder::PARAM_BOOL), IQueryBuilder::PARAM_BOOL),
+				)
+			)
+			->orderBy('updated_at', 'asc')
+			->orderBy('account_id', 'asc');
+		$messages = $this->findEntities($select);
+
+		if (empty($messages)) {
+			return [];
+		}
+
+		$ids = array_map(function (LocalMessage $message) {
+			return $message->getId();
+		}, $messages);
+
+		$attachments = $this->attachmentMapper->findByLocalMessageIds($ids);
+		$recipients = $this->recipientMapper->findByLocalMessageIds($ids);
+
+		$recipientMap = [];
+		foreach ($recipients as $r) {
+			$recipientMap[$r->getLocalMessageId()][] = $r;
+		}
+		$attachmentMap = [];
+		foreach ($attachments as $a) {
+			$attachmentMap[$a->getLocalMessageId()][] = $a;
+		}
+
+		return array_map(static function ($localMessage) use ($attachmentMap, $recipientMap) {
+			$localMessage->setAttachments($attachmentMap[$localMessage->getId()] ?? []);
+			$localMessage->setRecipients($recipientMap[$localMessage->getId()] ?? []);
+			return $localMessage;
+		}, $messages);
+	}
+
+	/**
 	 * @param Recipient[] $to
 	 * @param Recipient[] $cc
 	 * @param Recipient[] $bcc
diff --git a/lib/Events/DraftMessageCreatedEvent.php b/lib/Events/DraftMessageCreatedEvent.php
new file mode 100644
index 000000000..efd92290b
--- /dev/null
+++ b/lib/Events/DraftMessageCreatedEvent.php
@@ -0,0 +1,56 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * @copyright 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @author 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @license GNU AGPL version 3 or any later version
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as
+ * published by the Free Software Foundation, either version 3 of the
+ * License, or (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ */
+
+namespace OCA\Mail\Events;
+
+use OCA\Mail\Account;
+use OCA\Mail\Db\Message;
+use OCP\EventDispatcher\Event;
+
+/**
+ * @psalm-immutable
+ */
+class DraftMessageCreatedEvent extends Event {
+	/** @var Account */
+	private $account;
+
+	/** @var Message */
+	private $draft;
+
+	public function __construct(Account $account,
+								Message $draft) {
+		parent::__construct();
+		$this->account = $account;
+		$this->draft = $draft;
+	}
+
+	public function getAccount(): Account {
+		return $this->account;
+	}
+
+	public function getDraft(): ?Message {
+		return $this->draft;
+	}
+}
diff --git a/lib/Listener/DeleteDraftListener.php b/lib/Listener/DeleteDraftListener.php
index c615122d8..dc53778d1 100644
--- a/lib/Listener/DeleteDraftListener.php
+++ b/lib/Listener/DeleteDraftListener.php
@@ -31,6 +31,7 @@ use OCA\Mail\Account;
 use OCA\Mail\Db\Mailbox;
 use OCA\Mail\Db\MailboxMapper;
 use OCA\Mail\Db\Message;
+use OCA\Mail\Events\DraftMessageCreatedEvent;
 use OCA\Mail\Events\DraftSavedEvent;
 use OCA\Mail\Events\MessageDeletedEvent;
 use OCA\Mail\Events\OutboxMessageCreatedEvent;
@@ -71,7 +72,7 @@ class DeleteDraftListener implements IEventListener {
 	}
 
 	public function handle(Event $event): void {
-		if (($event instanceof DraftSavedEvent || $event instanceof OutboxMessageCreatedEvent) && $event->getDraft() !== null) {
+		if (($event instanceof DraftSavedEvent || $event instanceof OutboxMessageCreatedEvent || $event instanceof DraftMessageCreatedEvent) && $event->getDraft() !== null) {
 			$this->deleteDraft($event->getAccount(), $event->getDraft());
 		}
 	}
diff --git a/lib/Migration/Version2020Date20221103140538.php b/lib/Migration/Version2020Date20221103140538.php
new file mode 100644
index 000000000..e380ca88e
--- /dev/null
+++ b/lib/Migration/Version2020Date20221103140538.php
@@ -0,0 +1,59 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * @copyright Copyright (c) 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @author Anna Larch <anna.larch@gmx.net>
+ *
+ * @license GNU AGPL version 3 or any later version
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as
+ * published by the Free Software Foundation, either version 3 of the
+ * License, or (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program. If not, see <http://www.gnu.org/licenses/>.
+ *
+ */
+
+namespace OCA\Mail\Migration;
+
+use Closure;
+use OCP\DB\ISchemaWrapper;
+use OCP\DB\Types;
+use OCP\Migration\IOutput;
+use OCP\Migration\SimpleMigrationStep;
+
+class Version2020Date20221103140538 extends SimpleMigrationStep {
+	/**
+	 * @param IOutput $output
+	 * @param Closure(): ISchemaWrapper $schemaClosure
+	 * @psalm-param Closure $schemaClosure
+	 * @param array $options
+	 * @return null|ISchemaWrapper
+	 */
+	public function changeSchema(IOutput $output, Closure $schemaClosure, array $options): ?ISchemaWrapper {
+		/** @var ISchemaWrapper $schema */
+		$schema = $schemaClosure();
+
+		$localMessagesTable = $schema->getTable('mail_local_messages');
+		if (!$localMessagesTable->hasColumn('updated_at')) {
+			$localMessagesTable->addColumn('updated_at', Types::INTEGER, [
+				'notnull' => false,
+				'length' => 4,
+			]);
+		}
+		$localMessagesTable->changeColumn('send_at', [
+			'notnull' => false
+		]);
+		return $schema;
+	}
+}
diff --git a/lib/Service/DraftsService.php b/lib/Service/DraftsService.php
new file mode 100644
index 000000000..bee465378
--- /dev/null
+++ b/lib/Service/DraftsService.php
@@ -0,0 +1,240 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * Mail App
+ *
+ * @copyright 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @author Anna Larch <anna.larch@gmx.net>
+ *
+ * This library is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU AFFERO GENERAL PUBLIC LICENSE
+ * License as published by the Free Software Foundation; either
+ * version 3 of the License, or any later version.
+ *
+ * This library is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU AFFERO GENERAL PUBLIC LICENSE for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public
+ * License along with this library.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ */
+
+namespace OCA\Mail\Service;
+
+use OCA\Mail\Account;
+use OCA\Mail\Contracts\ILocalMailboxService;
+use OCA\Mail\Contracts\IMailManager;
+use OCA\Mail\Contracts\IMailTransmission;
+use OCA\Mail\Db\LocalMessage;
+use OCA\Mail\Db\LocalMessageMapper;
+use OCA\Mail\Db\Recipient;
+use OCA\Mail\Events\DraftMessageCreatedEvent;
+use OCA\Mail\Exception\ClientException;
+use OCA\Mail\Exception\NotImplemented;
+use OCA\Mail\Exception\ServiceException;
+use OCA\Mail\IMAP\IMAPClientFactory;
+use OCA\Mail\Service\Attachment\AttachmentService;
+use OCP\AppFramework\Db\DoesNotExistException;
+use OCP\AppFramework\Utility\ITimeFactory;
+use OCP\EventDispatcher\IEventDispatcher;
+use Psr\Log\LoggerInterface;
+use Throwable;
+
+class DraftsService implements ILocalMailboxService {
+	private IMailTransmission $transmission;
+	private LocalMessageMapper $mapper;
+	private AttachmentService $attachmentService;
+	private IEventDispatcher $eventDispatcher;
+	private IMAPClientFactory $clientFactory;
+	private IMailManager $mailManager;
+	private LoggerInterface $logger;
+	private AccountService $accountService;
+	private ITimeFactory $time;
+
+	public function __construct(IMailTransmission  $transmission,
+								LocalMessageMapper $mapper,
+								AttachmentService  $attachmentService,
+								IEventDispatcher    $eventDispatcher,
+								IMAPClientFactory $clientFactory,
+								IMailManager $mailManager,
+								LoggerInterface $logger,
+								AccountService $accountService,
+								ITimeFactory $time) {
+		$this->transmission = $transmission;
+		$this->mapper = $mapper;
+		$this->attachmentService = $attachmentService;
+		$this->eventDispatcher = $eventDispatcher;
+		$this->clientFactory = $clientFactory;
+		$this->mailManager = $mailManager;
+		$this->logger = $logger;
+		$this->accountService = $accountService;
+		$this->time = $time;
+	}
+
+	/**
+	 * @param array $recipients
+	 * @param int $type
+	 * @return Recipient[]
+	 */
+	private static function convertToRecipient(array $recipients, int $type): array {
+		return array_map(function ($recipient) use ($type) {
+			$r = new Recipient();
+			$r->setType($type);
+			$r->setLabel($recipient['label'] ?? $recipient['email']);
+			$r->setEmail($recipient['email']);
+			return $r;
+		}, $recipients);
+	}
+
+
+	public function deleteMessage(string $userId, LocalMessage $message): void {
+		$this->attachmentService->deleteLocalMessageAttachments($userId, $message->getId());
+		$this->mapper->deleteWithRecipients($message);
+	}
+
+	public function saveMessage(Account $account, LocalMessage $message, array $to, array $cc, array $bcc, array $attachments = []): LocalMessage {
+		$toRecipients = self::convertToRecipient($to, Recipient::TYPE_TO);
+		$ccRecipients = self::convertToRecipient($cc, Recipient::TYPE_CC);
+		$bccRecipients = self::convertToRecipient($bcc, Recipient::TYPE_BCC);
+
+		// if this message has a "sent at" datestamp and the type is set as Type Outbox
+		// check for a valid recipient
+		if ($message->getType() === LocalMessage::TYPE_OUTGOING && empty($toRecipients)) {
+			throw new ClientException('Cannot convert message to outbox message without at least one recipient');
+		}
+
+		$message = $this->mapper->saveWithRecipients($message, $toRecipients, $ccRecipients, $bccRecipients);
+
+		if (empty($attachments)) {
+			$message->setAttachments($attachments);
+			return $message;
+		}
+
+		$client = $this->clientFactory->getClient($account);
+		try {
+			$attachmentIds = $this->attachmentService->handleAttachments($account, $attachments, $client);
+		} finally {
+			$client->logout();
+		}
+
+		$message->setAttachments($this->attachmentService->saveLocalMessageAttachments($account->getUserId(), $message->getId(), $attachmentIds));
+		return $message;
+	}
+
+	public function updateMessage(Account $account, LocalMessage $message, array $to, array $cc, array $bcc, array $attachments = []): LocalMessage {
+		$toRecipients = self::convertToRecipient($to, Recipient::TYPE_TO);
+		$ccRecipients = self::convertToRecipient($cc, Recipient::TYPE_CC);
+		$bccRecipients = self::convertToRecipient($bcc, Recipient::TYPE_BCC);
+
+		// if this message has a "sent at" datestamp and the type is set as Type Outbox
+		// check for a valid recipient
+		if ($message->getType() === LocalMessage::TYPE_OUTGOING && empty($toRecipients)) {
+			throw new ClientException('Cannot convert message to outbox message without at least one recipient');
+		}
+
+		$message = $this->mapper->updateWithRecipients($message, $toRecipients, $ccRecipients, $bccRecipients);
+
+		if (empty($attachments)) {
+			$message->setAttachments($this->attachmentService->updateLocalMessageAttachments($account->getUserId(), $message, []));
+			return $message;
+		}
+
+		$client = $this->clientFactory->getClient($account);
+		try {
+			$attachmentIds = $this->attachmentService->handleAttachments($account, $attachments, $client);
+		} finally {
+			$client->logout();
+		}
+		$message->setAttachments($this->attachmentService->updateLocalMessageAttachments($account->getUserId(), $message, $attachmentIds));
+		return $message;
+	}
+
+	public function handleDraft(Account $account, int $draftId): void {
+		$message = $this->mailManager->getMessage($account->getUserId(), $draftId);
+		$this->eventDispatcher->dispatchTyped(new DraftMessageCreatedEvent($account, $message));
+	}
+
+	/**
+	 * "Send" the message
+	 *
+	 * @param LocalMessage $message
+	 * @param Account $account
+	 * @return void
+	 */
+	public function sendMessage(LocalMessage $message, Account $account): void {
+		try {
+			$this->transmission->sendLocalMessage($account, $message, true);
+		} catch (ClientException|ServiceException $e) {
+			$this->logger->error('Could not move draft to IMAP', ['exception' => $e]);
+			// Mark as failed so the message is not moved repeatedly in background
+			$message->setFailed(true);
+			$this->mapper->update($message);
+			throw $e;
+		}
+		$this->attachmentService->deleteLocalMessageAttachments($account->getUserId(), $message->getId());
+		$this->mapper->deleteWithRecipients($message);
+	}
+
+	/**
+	 * @throws DoesNotExistException
+	 */
+	public function getMessage(int $id, string $userId): LocalMessage {
+		return $this->mapper->findById($id, $userId);
+	}
+
+	/**
+	 * @throws NotImplemented
+	 */
+	public function getMessages(string $userId): array {
+		throw new NotImplemented('Not implemented');
+	}
+
+	public function flush() {
+		$messages = $this->mapper->findDueDrafts($this->time->getTime());
+		if (empty($messages)) {
+			return;
+		}
+
+		$accountIds = array_unique(array_map(function ($message) {
+			return $message->getAccountId();
+		}, $messages));
+
+		$accounts = array_combine($accountIds, array_map(function ($accountId) {
+			try {
+				return $this->accountService->findById($accountId);
+			} catch (DoesNotExistException $e) {
+				// The message belongs to a deleted account
+				return null;
+			}
+		}, $accountIds));
+
+		foreach ($messages as $message) {
+			try {
+				$account = $accounts[$message->getAccountId()];
+				if ($account === null) {
+					// Ignore message of non-existent account
+					continue;
+				}
+				$this->sendMessage(
+					$message,
+					$account,
+				);
+				$this->logger->debug('Draft {id} moved to IMAP', [
+					'id' => $message->getId(),
+				]);
+			} catch (Throwable $e) {
+				// Failure of one message should not stop sending other messages
+				// Log and continue
+				$this->logger->warning('Could not move draft {id} to IMAP: ' . $e->getMessage(), [
+					'id' => $message->getId(),
+					'exception' => $e,
+				]);
+			}
+		}
+	}
+}
diff --git a/lib/Service/MailTransmission.php b/lib/Service/MailTransmission.php
index 210bef244..4472809ad 100644
--- a/lib/Service/MailTransmission.php
+++ b/lib/Service/MailTransmission.php
@@ -218,7 +218,7 @@ class MailTransmission implements IMailTransmission {
 		);
 	}
 
-	public function sendLocalMessage(Account $account, LocalMessage $message): void {
+	public function sendLocalMessage(Account $account, LocalMessage $message, bool $isDraft = false): void {
 		$to = new AddressList(
 			array_map(
 				static function ($recipient) {
@@ -271,10 +271,14 @@ class MailTransmission implements IMailTransmission {
 			$alias = $this->aliasesService->find($message->getAliasId(), $account->getUserId());
 		}
 
-		try {
-			$this->sendMessage($messageData, $message->getInReplyToMessageId(), $alias ?? null);
-		} catch (SentMailboxNotSetException $e) {
-			throw new ClientException('Could not send message' . $e->getMessage(), (int)$e->getCode(), $e);
+		if ($isDraft) {
+			$this->saveDraft($messageData);
+		} else {
+			try {
+				$this->sendMessage($messageData, $message->getInReplyToMessageId(), $alias ?? null);
+			} catch (SentMailboxNotSetException $e) {
+				throw new ClientException('Could not send message' . $e->getMessage(), (int)$e->getCode(), $e);
+			}
 		}
 	}
 
diff --git a/tests/Unit/Service/DraftsServiceTest.php b/tests/Unit/Service/DraftsServiceTest.php
new file mode 100644
index 000000000..f5262b157
--- /dev/null
+++ b/tests/Unit/Service/DraftsServiceTest.php
@@ -0,0 +1,499 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * Mail App
+ *
+ * @copyright 2022 Anna Larch <anna.larch@gmx.net>
+ *
+ * @author Anna Larch <anna.larch@gmx.net>
+ *
+ * This library is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU AFFERO GENERAL PUBLIC LICENSE
+ * License as published by the Free Software Foundation; either
+ * version 3 of the License, or any later version.
+ *
+ * This library is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU AFFERO GENERAL PUBLIC LICENSE for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public
+ * License along with this library.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ */
+
+namespace OCA\Mail\Tests\Unit\Service;
+
+use ChristophWurst\Nextcloud\Testing\TestCase;
+use OC\EventDispatcher\EventDispatcher;
+use OCA\Mail\Account;
+use OCA\Mail\Contracts\IMailManager;
+use OCA\Mail\Db\LocalAttachment;
+use OCA\Mail\Db\LocalMessage;
+use OCA\Mail\Db\LocalMessageMapper;
+use OCA\Mail\Db\Recipient;
+use OCA\Mail\Exception\ClientException;
+use OCA\Mail\IMAP\IMAPClientFactory;
+use OCA\Mail\Service\AccountService;
+use OCA\Mail\Service\Attachment\AttachmentService;
+use OCA\Mail\Service\MailTransmission;
+use OCA\Mail\Service\OutboxService;
+use OCP\AppFramework\Db\DoesNotExistException;
+use OCP\AppFramework\Utility\ITimeFactory;
+use OCP\DB\Exception;
+use PHPUnit\Framework\MockObject\MockObject;
+use Psr\Log\LoggerInterface;
+
+class OutboxServiceTest extends TestCase {
+	/** @var MailTransmission|MockObject */
+	private $transmission;
+
+	/** @var LocalMessageMapper|MockObject */
+	private $mapper;
+
+	/** @var OutboxService */
+	private $outboxService;
+
+	/** @var string */
+	private $userId;
+
+	/** @var ITimeFactory|MockObject */
+	private $time;
+
+	/** @var AttachmentService|MockObject */
+	private $attachmentService;
+
+	/** @var IMAPClientFactory|MockObject */
+	private $clientFactory;
+
+	/** @var IMailManager|MockObject */
+	private $mailManager;
+
+	/** @var AccountService|MockObject */
+	private $accountService;
+
+	/** @var ITimeFactory|MockObject */
+	private $timeFactory;
+
+	/** @var MockObject|LoggerInterface */
+	private $logger;
+
+	protected function setUp(): void {
+		parent::setUp();
+
+		$this->transmission = $this->createMock(MailTransmission::class);
+		$this->mapper = $this->createMock(LocalMessageMapper::class);
+		$this->attachmentService = $this->createMock(AttachmentService::class);
+		$this->clientFactory = $this->createMock(IMAPClientFactory::class);
+		$this->mailManager = $this->createMock(IMailManager::class);
+		$this->accountService = $this->createMock(AccountService::class);
+		$this->timeFactory = $this->createMock(ITimeFactory::class);
+		$this->logger = $this->createMock(LoggerInterface::class);
+		$this->outboxService = new OutboxService(
+			$this->transmission,
+			$this->mapper,
+			$this->attachmentService,
+			$this->createMock(EventDispatcher::class),
+			$this->clientFactory,
+			$this->mailManager,
+			$this->accountService,
+			$this->timeFactory,
+			$this->logger,
+		);
+		$this->userId = 'linus';
+		$this->time = $this->createMock(ITimeFactory::class);
+	}
+
+	public function testGetMessages(): void {
+		$this->mapper->expects(self::once())
+			->method('getAllForUser')
+			->with($this->userId)
+			->willReturn([
+				[
+					'id' => 1,
+					'type' => 0,
+					'account_id' => 1,
+					'alias_id' => 2,
+					'send_at' => $this->time->getTime(),
+					'subject' => 'Test',
+					'body' => 'Test',
+					'html' => false,
+					'reply_to_id' => null,
+					'draft_id' => 99
+
+				],
+				[
+					'id' => 2,
+					'type' => 0,
+					'account_id' => 1,
+					'alias_id' => 2,
+					'send_at' => $this->time->getTime(),
+					'subject' => 'Second Test',
+					'body' => 'Second Test',
+					'html' => true,
+					'reply_to_id' => null,
+					'draft_id' => null
+				]
+			]);
+
+		$this->outboxService->getMessages($this->userId);
+	}
+
+	public function testGetMessagesNoneFound(): void {
+		$this->mapper->expects(self::once())
+			->method('getAllForUser')
+			->with($this->userId)
+			->willThrowException(new Exception());
+
+		$this->expectException(Exception::class);
+		$this->outboxService->getMessages($this->userId);
+	}
+
+	public function testGetMessage(): void {
+		$message = new LocalMessage();
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('abcd');
+
+		$this->mapper->expects(self::once())
+			->method('findById')
+			->with(1, $this->userId)
+			->willReturn($message);
+
+		$this->outboxService->getMessage(1, $this->userId);
+	}
+
+	public function testNoMessage(): void {
+		$this->mapper->expects(self::once())
+			->method('findById')
+			->with(1, $this->userId)
+			->willThrowException(new DoesNotExistException('Could not fetch any messages'));
+
+		$this->expectException(DoesNotExistException::class);
+		$this->outboxService->getMessage(1, $this->userId);
+	}
+
+	public function testDeleteMessage(): void {
+		$message = new LocalMessage();
+		$message->setId(10);
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('abcd');
+
+		$this->attachmentService->expects(self::once())
+			->method('deleteLocalMessageAttachments')
+			->with($this->userId, $message->getId());
+		$this->mapper->expects(self::once())
+			->method('deleteWithRecipients')
+			->with($message);
+
+		$this->outboxService->deleteMessage($this->userId, $message);
+	}
+
+	public function testSaveMessage(): void {
+		$message = new LocalMessage();
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('abcd');
+		$to = [
+			[
+				'label' => 'Lewis',
+				'email' => 'tent-living@startdewvalley.com',
+				'type' => Recipient::TYPE_TO,
+			]
+		];
+		$cc = [];
+		$bcc = [];
+		$attachments = [[]];
+		$attachmentIds = [1];
+		$rTo = Recipient::fromParams([
+			'label' => 'Lewis',
+			'email' => 'tent-living@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$message2 = $message;
+		$message2->setId(10);
+		$account = $this->createConfiguredMock(Account::class, [
+			'getUserId' => $this->userId
+		]);
+		$client = $this->createMock(\Horde_Imap_Client_Socket::class);
+
+		$this->mapper->expects(self::once())
+			->method('saveWithRecipients')
+			->with($message, [$rTo], $cc, $bcc)
+			->willReturn($message2);
+		$this->clientFactory->expects(self::once())
+			->method('getClient')
+			->with($account)
+			->willReturn($client);
+		$this->attachmentService->expects(self::once())
+			->method('handleAttachments')
+			->with($account, $attachments, $client)
+			->willReturn($attachmentIds);
+		$this->attachmentService->expects(self::once())
+			->method('saveLocalMessageAttachments')
+			->with($this->userId, 10, $attachmentIds);
+
+		$this->outboxService->saveMessage($account, $message, $to, $cc, $bcc, $attachments);
+	}
+
+	public function testSaveMessageNoAttachments(): void {
+		$message = new LocalMessage();
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('abcd');
+		$to = [
+			[
+				'label' => 'Lewis',
+				'email' => 'tent-living@startdewvalley.com',
+				'type' => Recipient::TYPE_TO,
+			]
+		];
+		$cc = [];
+		$bcc = [];
+		$attachments = [];
+		$rTo = Recipient::fromParams([
+			'label' => 'Lewis',
+			'email' => 'tent-living@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$message2 = $message;
+		$message2->setId(10);
+		$account = $this->createConfiguredMock(Account::class, [
+			'getUserId' => $this->userId
+		]);
+
+		$this->mapper->expects(self::once())
+			->method('saveWithRecipients')
+			->with($message, [$rTo], $cc, $bcc)
+			->willReturn($message2);
+		$this->clientFactory->expects(self::never())
+			->method('getClient');
+		$this->attachmentService->expects(self::never())
+			->method('handleAttachments');
+		$this->attachmentService->expects(self::never())
+			->method('saveLocalMessageAttachments');
+
+		$result = $this->outboxService->saveMessage($account, $message, $to, $cc, $bcc, $attachments);
+		$this->assertEquals($message2->getId(), $result->getId());
+		$this->assertEmpty($result->getAttachments());
+	}
+
+	public function testUpdateMessage(): void {
+		$message = new LocalMessage();
+		$message->setId(10);
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('abcd');
+		$old = Recipient::fromParams([
+			'label' => 'Pam',
+			'email' => 'BuyMeAnAle@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$message->setRecipients([$old]);
+		$to = [
+			[
+				'label' => 'Linus',
+				'email' => 'tent-living@startdewvalley.com',
+				'type' => Recipient::TYPE_TO,
+			]
+		];
+		$cc = [];
+		$bcc = [];
+		$attachments = [['type' => '']];
+		$attachmentIds = [3];
+		$rTo = Recipient::fromParams([
+			'label' => 'Linus',
+			'email' => 'tent-living@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$message2 = $message;
+		$message2->setRecipients([$rTo]);
+		$account = $this->createConfiguredMock(Account::class, [
+			'getUserId' => $this->userId
+		]);
+		$client = $this->createMock(\Horde_Imap_Client_Socket::class);
+
+		$this->mapper->expects(self::once())
+			->method('updateWithRecipients')
+			->with($message, [$rTo], $cc, $bcc)
+			->willReturn($message2);
+		$this->clientFactory->expects(self::once())
+			->method('getClient')
+			->with($account)
+			->willReturn($client);
+		$this->attachmentService->expects(self::once())
+			->method('handleAttachments')
+			->with($account, $attachments, $client)
+			->willReturn($attachmentIds);
+		$this->attachmentService->expects(self::once())
+			->method('updateLocalMessageAttachments')
+			->with($this->userId, $message2, $attachmentIds);
+
+		$this->outboxService->updateMessage($account, $message, $to, $cc, $bcc, $attachments);
+	}
+
+	public function testUpdateMessageNoAttachments(): void {
+		$message = new LocalMessage();
+		$message->setId(10);
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('abcd');
+		$old = Recipient::fromParams([
+			'label' => 'Pam',
+			'email' => 'BuyMeAnAle@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$message->setRecipients([$old]);
+		$to = [
+			[
+				'label' => 'Linus',
+				'email' => 'tent-living@startdewvalley.com',
+				'type' => Recipient::TYPE_TO,
+			]
+		];
+		$cc = [];
+		$bcc = [];
+		$attachments = [];
+		$rTo = Recipient::fromParams([
+			'label' => 'Linus',
+			'email' => 'tent-living@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$message2 = $message;
+		$message2->setRecipients([$rTo]);
+		$account = $this->createConfiguredMock(Account::class, [
+			'getUserId' => $this->userId
+		]);
+		$this->mapper->expects(self::once())
+			->method('updateWithRecipients')
+			->with($message, [$rTo], $cc, $bcc)
+			->willReturn($message2);
+		$this->attachmentService->expects(self::once())
+			->method('updateLocalMessageAttachments')
+			->with($this->userId, $message2, $attachments);
+		$this->clientFactory->expects(self::never())
+			->method('getClient');
+		$this->attachmentService->expects(self::never())
+			->method('handleAttachments');
+		$result = $this->outboxService->updateMessage($account, $message, $to, $cc, $bcc, $attachments);
+		$this->assertEmpty($result->getAttachments());
+	}
+
+	public function testSaveMessageError(): void {
+		$message = new LocalMessage();
+		$message->setAccountId(1);
+		$message->setSendAt($this->time->getTime());
+		$message->setSubject('Test');
+		$message->setBody('Test Test Test');
+		$message->setHtml(true);
+		$message->setInReplyToMessageId('laskdjhsakjh33233928@startdewvalley.com');
+		$to = [
+			[
+				'label' => 'Gunther',
+				'email' => 'museum@startdewvalley.com',
+				'type' => Recipient::TYPE_TO,
+			]
+		];
+		$rTo = Recipient::fromParams([
+			'label' => 'Gunther',
+			'email' => 'museum@startdewvalley.com',
+			'type' => Recipient::TYPE_TO,
+		]);
+		$account = $this->createMock(Account::class);
+
+		$this->mapper->expects(self::once())
+			->method('saveWithRecipients')
+			->with($message, [$rTo], [], [])
+			->willThrowException(new Exception());
+		$this->attachmentService->expects(self::never())
+			->method('saveLocalMessageAttachments');
+		$this->expectException(Exception::class);
+
+		$this->outboxService->saveMessage($account, $message, $to, [], []);
+	}
+
+	public function testSendMessage(): void {
+		$message = new LocalMessage();
+		$message->setId(1);
+		$recipient = new Recipient();
+		$recipient->setEmail('museum@startdewvalley.com');
+		$recipient->setLabel('Gunther');
+		$recipient->setType(Recipient::TYPE_TO);
+		$recipients = [$recipient];
+		$attachment = new LocalAttachment();
+		$attachment->setMimeType('image/png');
+		$attachment->setFileName('SlimesInTheMines.png');
+		$attachment->setCreatedAt($this->time->getTime());
+		$attachments = [$attachment];
+		$message->setRecipients($recipients);
+		$message->setAttachments($attachments);
+		$account = $this->createConfiguredMock(Account::class, [
+			'getUserId' => $this->userId
+		]);
+
+		$this->transmission->expects(self::once())
+			->method('sendLocalMessage')
+			->with($account, $message);
+		$this->attachmentService->expects(self::once())
+			->method('deleteLocalMessageAttachments')
+			->with($account->getUserId(), $message->getId());
+		$this->mapper->expects(self::once())
+			->method('deleteWithRecipients')
+			->with($message);
+
+		$this->outboxService->sendMessage($message, $account);
+	}
+
+	public function testSendMessageTransmissionError(): void {
+		$message = new LocalMessage();
+		$message->setId(1);
+		$recipient = new Recipient();
+		$recipient->setEmail('museum@startdewvalley.com');
+		$recipient->setLabel('Gunther');
+		$recipient->setType(Recipient::TYPE_TO);
+		$recipients = [$recipient];
+		$attachment = new LocalAttachment();
+		$attachment->setMimeType('image/png');
+		$attachment->setFileName('SlimesInTheMines.png');
+		$attachment->setCreatedAt($this->time->getTime());
+		$attachments = [$attachment];
+		$message->setRecipients($recipients);
+		$message->setAttachments($attachments);
+		$account = $this->createConfiguredMock(Account::class, [
+			'getUserId' => $this->userId
+		]);
+
+		$this->transmission->expects(self::once())
+			->method('sendLocalMessage')
+			->with($account, $message)
+			->willThrowException(new ClientException());
+		$this->attachmentService->expects(self::never())
+			->method('deleteLocalMessageAttachments');
+		$this->mapper->expects(self::never())
+			->method('deleteWithRecipients');
+
+		$this->expectException(ClientException::class);
+		$this->outboxService->sendMessage($message, $account);
+	}
+}