diff --git a/ElementX/Sources/Screens/Timeline/TimelineModels.swift b/ElementX/Sources/Screens/Timeline/TimelineModels.swift
index ca85a6cbb..7d327029b 100644
--- a/ElementX/Sources/Screens/Timeline/TimelineModels.swift
+++ b/ElementX/Sources/Screens/Timeline/TimelineModels.swift
@@ -222,7 +222,7 @@ struct ReadReceiptSummaryInfo: Identifiable {
 enum TimelineAlertInfoType: Hashable {
     case audioRecodingPermissionError
     case pollEndConfirmation(String)
-    case sendingFailed
+    case sendingFailed(reason: String?, itemID: TimelineItemIdentifier)
     case encryptionAuthenticity(String)
     case encryptionForwarder(String)
     case inviteAgain
diff --git a/ElementX/Sources/Screens/Timeline/TimelineViewModel.swift b/ElementX/Sources/Screens/Timeline/TimelineViewModel.swift
index 76e5a83aa..f9528d0db 100644
--- a/ElementX/Sources/Screens/Timeline/TimelineViewModel.swift
+++ b/ElementX/Sources/Screens/Timeline/TimelineViewModel.swift
@@ -738,8 +738,8 @@ class TimelineViewModel: TimelineViewModelType, TimelineViewModelProtocol {
             fatalError("Only events can have send info.")
         }
         
-        if case .sendingFailed(.unknown) = eventTimelineItem.properties.deliveryStatus {
-            displayAlert(.sendingFailed)
+        if case let .sendingFailed(.unknown(reason)) = eventTimelineItem.properties.deliveryStatus {
+            displayAlert(.sendingFailed(reason: reason, itemID: itemID))
         } else if case let .sendingFailed(.verifiedUser(failure)) = eventTimelineItem.properties.deliveryStatus {
             guard let sendHandle = timelineController.sendHandle(for: itemID) else {
                 MXLog.error("Cannot find send handle for \(itemID).")
@@ -755,6 +755,27 @@ class TimelineViewModel: TimelineViewModelType, TimelineViewModelProtocol {
             displayAlert(.encryptionAuthenticity(authenticityMessage))
         }
     }
+
+    private func retrySending(itemID: TimelineItemIdentifier) {
+        guard let sendHandle = timelineController.sendHandle(for: itemID) else {
+            MXLog.error("Cannot find send handle for \(itemID).")
+            return
+        }
+
+        Task {
+            if case .failure(let error) = await sendHandle.resend() {
+                MXLog.error("Failed retrying to send \(itemID): \(error)")
+            }
+        }
+    }
+
+    private func removeFailedMessage(itemID: TimelineItemIdentifier) {
+        guard case let .event(_, eventOrTransactionID) = itemID else {
+            fatalError("Only events can fail to send.")
+        }
+
+        Task { await timelineController.redact(eventOrTransactionID) }
+    }
     
     private func slashCommand(message: String) -> SlashCommand? {
         for command in SlashCommand.allCases where message.starts(with: command.rawValue) {
@@ -1103,10 +1124,13 @@ class TimelineViewModel: TimelineViewModelType, TimelineViewModelProtocol {
                                              message: L10n.commonPollEndConfirmation,
                                              primaryButton: .init(title: L10n.actionCancel, role: .cancel, action: nil),
                                              secondaryButton: .init(title: L10n.actionOk) { self.timelineInteractionHandler.endPoll(pollStartID: pollStartID) })
-        case .sendingFailed:
+        case .sendingFailed(let reason, let itemID):
             state.bindings.alertInfo = .init(id: type,
                                              title: L10n.commonSendingFailed,
-                                             primaryButton: .init(title: L10n.actionOk, action: nil))
+                                             message: reason,
+                                             primaryButton: .init(title: L10n.actionCancel, role: .cancel, action: nil),
+                                             verticalButtons: [.init(title: L10n.actionRetry) { [weak self] in self?.retrySending(itemID: itemID) },
+                                                               .init(title: L10n.actionRemoveMessage, role: .destructive) { [weak self] in self?.removeFailedMessage(itemID: itemID) }])
         case .encryptionAuthenticity(let message):
             state.bindings.alertInfo = .init(id: type,
                                              title: message,
diff --git a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift
index d16cb49b1..d9a418832 100644
--- a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift
+++ b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift
@@ -262,7 +262,7 @@ struct TimelineItemMenu_Previews: PreviewProvider, TestablePreview {
     static let (backupItem, _) = makeActions(authenticity: .notGuaranteed(color: .gray))
     static let (unsignedItem, _) = makeActions(authenticity: .unsignedDevice(color: .red))
     static let (unencryptedItem, _) = makeActions(authenticity: .sentInClear(color: .red))
-    static let (unknownFailureItem, _) = makeActions(deliveryStatus: .sendingFailed(.unknown))
+    static let (unknownFailureItem, _) = makeActions(deliveryStatus: .sendingFailed(.unknown(reason: nil)))
     static let (identityChangedItem, _) = makeActions(deliveryStatus: .sendingFailed(.verifiedUser(.changedIdentity(users: [
         "@alice:matrix.org"
     ]))))
diff --git a/ElementX/Sources/Screens/Timeline/View/Style/TimelineStyler.swift b/ElementX/Sources/Screens/Timeline/View/Style/TimelineStyler.swift
index e2d16acee..d1feef6c7 100644
--- a/ElementX/Sources/Screens/Timeline/View/Style/TimelineStyler.swift
+++ b/ElementX/Sources/Screens/Timeline/View/Style/TimelineStyler.swift
@@ -92,7 +92,7 @@ struct TimelineItemStyler_Previews: PreviewProvider, TestablePreview {
     
     static let failed: TextRoomTimelineItem = {
         var result = base
-        result.properties.deliveryStatus = .sendingFailed(.unknown)
+        result.properties.deliveryStatus = .sendingFailed(.unknown(reason: nil))
         return result
     }()
     
diff --git a/ElementX/Sources/Services/Timeline/TimelineItemProxy.swift b/ElementX/Sources/Services/Timeline/TimelineItemProxy.swift
index c897ecd22..69a744b44 100644
--- a/ElementX/Sources/Services/Timeline/TimelineItemProxy.swift
+++ b/ElementX/Sources/Services/Timeline/TimelineItemProxy.swift
@@ -65,7 +65,7 @@ nonisolated enum TimelineItemSendFailure: Hashable {
     }
     
     case verifiedUser(VerifiedUser)
-    case unknown
+    case unknown(reason: String?)
 }
 
 /// A light wrapper around event timeline items returned from Rust.
@@ -95,8 +95,10 @@ final nonisolated class EventTimelineItemProxy: Sendable {
                 return .sendingFailed(.verifiedUser(.changedIdentity(users: users)))
             case .insecureDevices(let userDeviceMap):
                 return .sendingFailed(.verifiedUser(.hasUnsignedDevice(devices: userDeviceMap)))
+            case .genericApiError(let message):
+                return .sendingFailed(.unknown(reason: message))
             default:
-                return .sendingFailed(.unknown)
+                return .sendingFailed(.unknown(reason: nil))
             }
         case .notSentYet:
             return .sending