diff --git a/NextcloudTalk/Chat/BaseChatViewController.swift b/NextcloudTalk/Chat/BaseChatViewController.swift
index 6fc3dd74e..0b367fc75 100644
--- a/NextcloudTalk/Chat/BaseChatViewController.swift
+++ b/NextcloudTalk/Chat/BaseChatViewController.swift
@@ -1360,6 +1360,15 @@ import Toast
         NotificationPresenter.shared().present(text: NSLocalizedString("Message unpinned", comment: ""), dismissAfterDelay: 5.0, includedStyle: .success)
     }
 
+    internal func prepareVoiceMessageForResend(_ message: NCChatMessage) {
+        message.sendingFailed = false
+        message.isOfflineMessage = false
+
+        // Like a resent text message, the message is sent now: it needs to be placed at the end of the chat
+        // and must not expire (getTemporaryMessages) based on the timestamp of the failed attempt
+        message.timestamp = Int(Date().timeIntervalSince1970)
+    }
+
     func didPressResend(for message: NCChatMessage) {
         // Make sure there's no unread message separator, as the indexpath could be invalid after removing a message
         self.removeUnreadMessagesSeparator()
@@ -1371,6 +1380,13 @@ import Toast
         if message.messageType != kMessageTypeVoiceMessage {
             self.sendChatMessage(message: originalMessage, withParentMessage: message.parent, messageParameters: message.messageParametersJSONString ?? "", silently: message.isSilent)
         } else {
+            // Show and store the message as sending again, so it can be marked as failed again
+            self.prepareVoiceMessageForResend(message)
+
+            RLMRealm.writeTransaction { realm in
+                realm.addOrUpdate(NCChatMessage(value: message))
+            }
+
             if NCDatabaseManager.sharedInstance().roomHasTalkCapability(.chatReferenceId, for: room) {
                 self.appendTemporaryMessage(temporaryMessage: message)
             }
@@ -2245,11 +2261,33 @@ import Toast
                 try await ChatFileUploader.upload(upload)
                 NCLog.log("Successfully uploaded and shared \(upload.fileName)")
             } catch {
+                if let referenceId = upload.referenceId {
+                    self.markTemporaryMessageAsFailed(referenceId: referenceId)
+                }
+
                 self.presentUploadError(error, for: upload)
             }
         }
     }
 
+    internal func markTemporaryMessageAsFailed(referenceId: String) {
+        // Allow to resend or delete the message, instead of showing it as sending until it expires
+        RLMRealm.writeTransaction { _ in
+            if let managedTemporaryMessage = NCChatMessage.objects(where: "referenceId = %@ AND isTemporary = true", referenceId).firstObject() as? NCChatMessage {
+                managedTemporaryMessage.sendingFailed = true
+                managedTemporaryMessage.isOfflineMessage = false
+            }
+        }
+
+        self.modifyMessageWith(referenceId: referenceId) { message in
+            // The message might have been received from the server in the meantime
+            guard message.isTemporary else { return }
+
+            message.sendingFailed = true
+            message.isOfflineMessage = false
+        }
+    }
+
     private func presentUploadError(_ error: Error, for upload: ChatFileUpload) {
         let message: String
 
@@ -2270,6 +2308,9 @@ import Toast
         case ChatFileUploadError.tooManyRequests:
             NCLog.log("Too many requests while uploading")
             message = NSLocalizedString("Too many requests, please try again later", comment: "")
+        case ChatFileUploadError.uploadFailed(_, let errorDescription) where !errorDescription.isEmpty:
+            NCLog.log("Failed to upload \(upload.fileName). Error: \(errorDescription)")
+            message = errorDescription
         default:
             NCLog.log("Failed to upload \(upload.fileName). Error: \(error.localizedDescription)")
             message = NSLocalizedString("Unknown error occurred", comment: "")
diff --git a/NextcloudTalkTests/Unit/Chat/UnitBaseChatViewControllerTest.swift b/NextcloudTalkTests/Unit/Chat/UnitBaseChatViewControllerTest.swift
index 83424e8f9..c765ae6dd 100644
--- a/NextcloudTalkTests/Unit/Chat/UnitBaseChatViewControllerTest.swift
+++ b/NextcloudTalkTests/Unit/Chat/UnitBaseChatViewControllerTest.swift
@@ -222,4 +222,58 @@ final class UnitBaseChatViewControllerTest: TestBaseRealm {
         XCTAssertEqual(baseController.getCellHeight(for: testMessage, with: 300), 171.0)
     }
 
+    func testMarkTemporaryMessageAsFailed() throws {
+        let temporaryMessage = NCChatMessage()
+        temporaryMessage.internalId = "temp-1"
+        temporaryMessage.referenceId = "reference-1"
+        temporaryMessage.messageType = "voice-message"
+        temporaryMessage.isTemporary = true
+
+        // A message received from the server with the same reference id
+        let receivedMessage = NCChatMessage()
+        receivedMessage.messageId = 1
+        receivedMessage.internalId = "internal-1"
+        receivedMessage.referenceId = "reference-1"
+
+        try? realm.transaction {
+            realm.add(temporaryMessage)
+            realm.add(receivedMessage)
+        }
+
+        baseController.markTemporaryMessageAsFailed(referenceId: "reference-1")
+
+        XCTAssertTrue(temporaryMessage.sendingFailed)
+        XCTAssertFalse(temporaryMessage.isOfflineMessage)
+        XCTAssertFalse(receivedMessage.sendingFailed)
+    }
+
+    func testMarkTemporaryMessageAsFailedIgnoresReceivedMessage() throws {
+        let receivedMessage = NCChatMessage()
+        receivedMessage.messageId = 1
+        receivedMessage.internalId = "internal-1"
+        receivedMessage.referenceId = "reference-1"
+
+        try? realm.transaction {
+            realm.add(receivedMessage)
+        }
+
+        baseController.markTemporaryMessageAsFailed(referenceId: "reference-1")
+
+        XCTAssertFalse(receivedMessage.sendingFailed)
+    }
+
+    func testPrepareVoiceMessageForResendAssignsNewTimestamp() throws {
+        let message = NCChatMessage()
+        message.sendingFailed = true
+        message.isOfflineMessage = true
+        message.timestamp = Int(Date().timeIntervalSince1970) - (60 * 60 * 13)
+
+        let before = Int(Date().timeIntervalSince1970)
+        baseController.prepareVoiceMessageForResend(message)
+
+        XCTAssertFalse(message.sendingFailed)
+        XCTAssertFalse(message.isOfflineMessage)
+        XCTAssertGreaterThanOrEqual(message.timestamp, before)
+    }
+
 }