diff --git a/lib/Controller/OutboxController.php b/lib/Controller/OutboxController.php
index 382333dabc..3dadf7f811 100644
--- a/lib/Controller/OutboxController.php
+++ b/lib/Controller/OutboxController.php
@@ -221,6 +221,10 @@ public function update(
 		$message->setSmimeEncrypt($smimeEncrypt);
 		$message->setRequestMdn($requestMdn);
 
+		// Updating the message should reset its status. Else it's impossible to
+		// retry an erroneous one.
+		$message->setStatus(LocalMessage::STATUS_RAW);
+
 		if (!empty($smimeCertificateId)) {
 			$smimeCertificate = $this->smimeService->findCertificate($smimeCertificateId, $this->userId);
 			$message->setSmimeCertificateId($smimeCertificate->getId());
diff --git a/lib/Service/OutboxService.php b/lib/Service/OutboxService.php
index d8f3247c0e..7778073e54 100644
--- a/lib/Service/OutboxService.php
+++ b/lib/Service/OutboxService.php
@@ -172,6 +172,9 @@ public function updateMessage(Account $account, LocalMessage $message, array $to
 		$ccRecipients = self::convertToRecipient($cc, Recipient::TYPE_CC);
 		$bccRecipients = self::convertToRecipient($bcc, Recipient::TYPE_BCC);
 
+		// The message is changed, so any previous error should be ignored
+		$message->setFailed(false);
+
 		$message = $this->mapper->updateWithRecipients($message, $toRecipients, $ccRecipients, $bccRecipients);
 
 		if ($attachments === []) {