Added a timeout for the MessageSendJob and additional logging

SessionMessagingKit/Database/Models/Attachment.swift

@@ -990,7 +990,7 @@ extension Attachment {
         return downloadUrl
             .map { urlString -> String? in
                 urlString
-                    .split(separator: "/")
+                    .split(separator: "/")  // stringlint:disable
                     .last
                     .map { String($0) }
             }

SessionMessagingKit/Jobs/Types/MessageSendJob.swift

@@ -163,7 +163,8 @@ public enum MessageSendJob: JobExecutor {
         // Store the sentTimestamp from the message in case it fails due to a clockOutOfSync error
         let originalSentTimestamp: UInt64? = details.message.sentTimestamp
         
-        /// Perform the actual message sending
+        /// Perform the actual message sending - this will timeout if the entire process takes longer than `HTTP.defaultTimeout * 2`
+        /// which can occur if it needs to build a new onion path (which doesn't actually have any limits so can take forever in rare cases)
         ///
         /// **Note:** No need to upload attachments as part of this process as the above logic splits that out into it's own job
         /// so we shouldn't get here until attachments have already been uploaded
@@ -183,13 +184,23 @@ public enum MessageSendJob: JobExecutor {
             .flatMap { MessageSender.sendImmediate(data: $0, using: dependencies) }
             .subscribe(on: queue, using: dependencies)
             .receive(on: queue, using: dependencies)
+            .timeout(.milliseconds(Int(HTTP.defaultTimeout * 2 * 1000)), scheduler: queue, customError: {
+                MessageSenderError.sendJobTimeout
+            })
             .sinkUntilComplete(
                 receiveCompletion: { result in
                     switch result {
                         case .finished: success(job, false, dependencies)
                         case .failure(let error):
-                            SNLog("[MessageSendJob] Couldn't send message due to error: \(error).")
+                            switch error {
+                                case MessageSenderError.sendJobTimeout:
+                                    SNLog("[MessageSendJob] Couldn't send message due to error: \(error) (paths: \(OnionRequestAPI.paths.prettifiedDescription)).")
+                                    
+                                default:
+                                    SNLog("[MessageSendJob] Couldn't send message due to error: \(error).")
+                            }
                             
+                            // Actual error handling
                             switch error {
                                 case let senderError as MessageSenderError where !senderError.isRetryable:
                                     failure(job, error, true, dependencies)

SessionMessagingKit/Sending & Receiving/Errors/MessageSenderError.swift

@@ -14,6 +14,7 @@ public enum MessageSenderError: LocalizedError, Equatable {
     case noUsername
     case attachmentsNotUploaded
     case blindingFailed
+    case sendJobTimeout
     
     // Closed groups
     case noThread
@@ -43,6 +44,7 @@ public enum MessageSenderError: LocalizedError, Equatable {
             case .noUsername: return "Missing username."
             case .attachmentsNotUploaded: return "Attachments for this message have not been uploaded."
             case .blindingFailed: return "Couldn't blind the sender"
+            case .sendJobTimeout: return "Send job timeout (likely due to path building taking too long)."
             
             // Closed groups
             case .noThread: return "Couldn't find a thread associated with the given group public key."
@@ -66,6 +68,7 @@ public enum MessageSenderError: LocalizedError, Equatable {
             case (.noKeyPair, .noKeyPair): return true
             case (.invalidClosedGroupUpdate, .invalidClosedGroupUpdate): return true
             case (.blindingFailed, .blindingFailed): return true
+            case (.sendJobTimeout, .sendJobTimeout): return true
             
             case (.other(let lhsError), .other(let rhsError)):
                 // Not ideal but the best we can do

SessionSnodeKit/Networking/OnionRequestAPI.swift

@@ -547,10 +547,10 @@ public enum OnionRequestAPI {
                     switch result {
                         case .finished: break
                         case .failure(let error):
-                            guard
+                            guard let guardSnode: Snode = guardSnode else {
-                                case HTTPError.httpRequestFailed(let statusCode, let data) = error,
+                                return SNLog("Request failed with no guardSnode.")
-                                let guardSnode: Snode = guardSnode
+                            }
-                            else { return }
+                            guard case HTTPError.httpRequestFailed(let statusCode, let data) = error else { return }
                             
                             let path = paths.first { $0.contains(guardSnode) }