diff --git a/lib/Chat/ChatManager.php b/lib/Chat/ChatManager.php
index 387bf6dd0a8..dd159c1c706 100644
--- a/lib/Chat/ChatManager.php
+++ b/lib/Chat/ChatManager.php
@@ -645,12 +645,21 @@ public function deleteMessage(Room $chat, IComment $comment, Participant $partic
 
 		$this->commentsManager->save($comment);
 
-		$this->attachmentService->deleteAttachmentByMessageId((int)$comment->getId());
+		$messageId = (int)$comment->getId();
+		$this->attachmentService->deleteAttachmentByMessageId($messageId);
 
 		$this->referenceManager->invalidateCache($chat->getToken());
 
 		$this->unreadCountCache->clear($chat->getId() . '-');
 
+		if ($chat->getLastPinnedId() === $messageId) {
+			$pinnedMessages = $this->attachmentService->getAttachmentsByType($chat, Attachment::TYPE_PINNED, 0, 1);
+			if (!empty($pinnedMessages)) {
+				$pinnedMessage = array_shift($pinnedMessages);
+				$this->roomService->setLastPinnedId($chat, $pinnedMessage->getMessageId());
+			}
+		}
+
 		return $this->addSystemMessage(
 			$chat,
 			$participant,
diff --git a/tests/integration/features/chat-1/pinned-messages.feature b/tests/integration/features/chat-1/pinned-messages.feature
index fc634a974fd..62579f29b7f 100644
--- a/tests/integration/features/chat-1/pinned-messages.feature
+++ b/tests/integration/features/chat-1/pinned-messages.feature
@@ -89,3 +89,20 @@ Feature: chat-1/pinned-messages
     Then user "participant2" is participant of the following rooms (v4)
       | id   | type | lastPinnedId | hiddenPinnedId |
       | room | 3    | EMPTY        | EMPTY          |
+
+  Scenario: Deleting last pinned message
+    Given user "participant1" creates room "room" (v4)
+      | roomType | 3 |
+      | roomName | room |
+    And user "participant1" adds user "participant2" to room "room" with 200 (v4)
+    When user "participant1" sends message "Message 1" to room "room" with 201
+    When user "participant1" pins message "Message 1" in room "room" with 200
+    When user "participant1" sends message "Message 2" to room "room" with 201
+    When user "participant1" pins message "Message 2" in room "room" with 200
+    Then user "participant2" is participant of the following rooms (v4)
+      | id   | type | lastPinnedId | hiddenPinnedId |
+      | room | 3    | Message 2    | EMPTY          |
+    When user "participant1" deletes message "Message 2" from room "room" with 200
+    Then user "participant2" is participant of the following rooms (v4)
+      | id   | type | lastPinnedId | hiddenPinnedId |
+      | room | 3    | Message 1    | EMPTY          |