diff --git a/ConversationsClassic/AppCore/Actions/SharingActions.swift b/ConversationsClassic/AppCore/Actions/SharingActions.swift
index f1db341..901358a 100644
--- a/ConversationsClassic/AppCore/Actions/SharingActions.swift
+++ b/ConversationsClassic/AppCore/Actions/SharingActions.swift
@@ -16,4 +16,6 @@ enum SharingAction: Stateable {
     case galleryItemsUpdated(items: [SharingGalleryItem])
 
     case cameraCaptured(media: Data, type: SharingCameraMediaType)
+
+    case retrySharing(messageId: String)
 }
diff --git a/ConversationsClassic/AppCore/Middlewares/DatabaseMiddleware.swift b/ConversationsClassic/AppCore/Middlewares/DatabaseMiddleware.swift
index 0972ee5..b95185a 100644
--- a/ConversationsClassic/AppCore/Middlewares/DatabaseMiddleware.swift
+++ b/ConversationsClassic/AppCore/Middlewares/DatabaseMiddleware.swift
@@ -395,6 +395,29 @@ final class DatabaseMiddleware {
             }
             .eraseToAnyPublisher()
 
+        case .sharingAction(.retrySharing(let id)):
+            return Future<AppAction, Never> { promise in
+                Task(priority: .background) { [weak self] in
+                    guard let database = self?.database else {
+                        promise(.success(.databaseAction(.storeMessageFailed(reason: L10n.Global.Error.genericDbError)))
+                        )
+                        return
+                    }
+                    do {
+                        _ = try database._db.write { db in
+                            try Message
+                                .filter(Column("id") == id)
+                                .updateAll(db, Column("pending").set(to: true), Column("sentError").set(to: false))
+                        }
+                        promise(.success(.empty))
+                    } catch {
+                        promise(.success(.databaseAction(.storeMessageFailed(reason: error.localizedDescription)))
+                        )
+                    }
+                }
+            }
+            .eraseToAnyPublisher()
+
         case .xmppAction(.xmppAttachmentUploadSuccess(let messageId, let remotePath)):
             return Future<AppAction, Never> { promise in
                 Task(priority: .background) { [weak self] in
@@ -407,7 +430,7 @@ final class DatabaseMiddleware {
                         _ = try database._db.write { db in
                             try Message
                                 .filter(Column("id") == messageId)
-                                .updateAll(db, Column("attachmentRemotePath").set(to: remotePath), Column("pending").set(to: false))
+                                .updateAll(db, Column("attachmentRemotePath").set(to: remotePath), Column("pending").set(to: false), Column("sentError").set(to: false))
                         }
                         promise(.success(.empty))
                     } catch {
diff --git a/ConversationsClassic/View/Screens/Conversation/ConversationMessageContainer.swift b/ConversationsClassic/View/Screens/Conversation/ConversationMessageContainer.swift
index 0a1687b..2c134d9 100644
--- a/ConversationsClassic/View/Screens/Conversation/ConversationMessageContainer.swift
+++ b/ConversationsClassic/View/Screens/Conversation/ConversationMessageContainer.swift
@@ -70,7 +70,7 @@ private struct AttachmentView: View {
     let message: Message
 
     var body: some View {
-        if message.attachmentDownloadFailed {
+        if message.attachmentDownloadFailed || (message.attachmentLocalName != nil && message.sentError) {
             failed
         } else {
             switch message.attachmentType {
@@ -134,6 +134,8 @@ private struct AttachmentView: View {
             .onTapGesture {
                 if let url = message.attachmentRemotePath {
                     store.dispatch(.fileAction(.downloadAttachmentFile(messageId: message.id, attachmentRemotePath: url)))
+                } else if message.attachmentLocalName != nil && message.sentError {
+                    store.dispatch(.sharingAction(.retrySharing(messageId: message.id)))
                 }
             }
     }