Attempt to resend pending messages if job creation failed.

app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java

@@ -62,6 +62,7 @@ import org.thoughtcrime.securesms.jobs.CheckServiceReachabilityJob;
 import org.thoughtcrime.securesms.jobs.DownloadLatestEmojiDataJob;
 import org.thoughtcrime.securesms.jobs.EmojiSearchIndexDownloadJob;
 import org.thoughtcrime.securesms.jobs.FcmRefreshJob;
+import org.thoughtcrime.securesms.jobs.RetryPendingSendsJob;
 import org.thoughtcrime.securesms.jobs.FontDownloaderJob;
 import org.thoughtcrime.securesms.jobs.GroupRingCleanupJob;
 import org.thoughtcrime.securesms.jobs.GroupV2UpdateSelfProfileKeyJob;
@@ -110,7 +111,6 @@ import org.thoughtcrime.securesms.util.TextSecurePreferences;
 import org.thoughtcrime.securesms.util.Util;
 import org.thoughtcrime.securesms.util.VersionTracker;
 import org.thoughtcrime.securesms.util.dynamiclanguage.DynamicLanguageContextWrapper;
-import org.whispersystems.signalservice.api.backup.MediaName;
 import org.whispersystems.signalservice.api.websocket.SignalWebSocket;
 
 import java.io.InterruptedIOException;
@@ -229,6 +229,7 @@ public class ApplicationContext extends Application implements AppForegroundObse
                             .addPostRender(() -> ActiveCallManager.clearNotifications(this))
                             .addPostRender(() -> GroupSendEndorsementInternalNotifier.init())
                             .addPostRender(RestoreOptimizedMediaJob::enqueueIfNecessary)
+                            .addPostRender(RetryPendingSendsJob::enqueueForAll)
                             .execute();
 
     Log.d(TAG, "onCreate() took " + (System.currentTimeMillis() - startTime) + " ms");

app/src/main/java/org/thoughtcrime/securesms/database/MessageTable.kt

@@ -146,6 +146,8 @@ import java.util.UUID
 import java.util.function.Function
 import kotlin.math.max
 import kotlin.math.min
+import kotlin.time.Duration.Companion.days
+import kotlin.time.Duration.Companion.milliseconds
 
 open class MessageTable(context: Context?, databaseHelper: SignalDatabase) : DatabaseTable(context, databaseHelper), MessageTypes, RecipientIdDatabaseReference, ThreadIdDatabaseReference {
 
@@ -1997,6 +1999,19 @@ open class MessageTable(context: Context?, databaseHelper: SignalDatabase) : Dat
     }
   }
 
+  fun getRecentPendingMessages(): MmsReader {
+    val now = System.currentTimeMillis()
+    val oneDayAgo = now.milliseconds - 1.days
+    val messageIds = readableDatabase
+      .select(ID)
+      .from(TABLE_NAME)
+      .where("$DATE_SENT > ${oneDayAgo.inWholeMilliseconds} AND $DATE_SENT < $now AND ($TYPE & ${MessageTypes.BASE_TYPE_MASK}) = ${MessageTypes.BASE_SENDING_TYPE} AND $SCHEDULED_DATE = -1")
+      .run()
+      .readToList { it.requireLong(ID) }
+
+    return getMessages(messageIds)
+  }
+
   private fun getOriginalEditedMessageRecord(messageId: Long): Long {
     return readableDatabase.select(ID)
       .from(TABLE_NAME)
@@ -5304,15 +5319,6 @@ open class MessageTable(context: Context?, databaseHelper: SignalDatabase) : Dat
     val type: Long
   )
 
-  enum class MessageStatus {
-    PENDING,
-    SENT,
-    DELIVERED,
-    READ,
-    VIEWED,
-    FAILED
-  }
-
   data class SyncMessageId(
     val recipientId: RecipientId,
     val timetamp: Long

app/src/main/java/org/thoughtcrime/securesms/jobs/JobManagerFactories.java

@@ -256,6 +256,8 @@ public final class JobManagerFactories {
       put(SyncSystemContactLinksJob.KEY,               new SyncSystemContactLinksJob.Factory());
       put(MultiDeviceStorySendSyncJob.KEY,             new MultiDeviceStorySendSyncJob.Factory());
       put(ResetSvrGuessCountJob.KEY,                   new ResetSvrGuessCountJob.Factory());
+      put(RetryPendingSendsJob.KEY,                    new RetryPendingSendsJob.Factory());
+      put(RetryPendingSendSecondCheckJob.KEY,          new RetryPendingSendSecondCheckJob.Factory());
       put(ServiceOutageDetectionJob.KEY,               new ServiceOutageDetectionJob.Factory());
       put(StickerDownloadJob.KEY,                      new StickerDownloadJob.Factory());
       put(StickerPackDownloadJob.KEY,                  new StickerPackDownloadJob.Factory());

app/src/main/java/org/thoughtcrime/securesms/jobs/RetryPendingSendSecondCheckJob.kt

@@ -0,0 +1,66 @@
+/*
+ * Copyright 2025 Signal Messenger, LLC
+ * SPDX-License-Identifier: AGPL-3.0-only
+ */
+
+package org.thoughtcrime.securesms.jobs
+
+import org.signal.core.util.logging.Log
+import org.thoughtcrime.securesms.database.SignalDatabase
+import org.thoughtcrime.securesms.database.model.MessageId
+import org.thoughtcrime.securesms.jobmanager.Job
+import org.thoughtcrime.securesms.jobs.protos.SecondRoundFixupSendJobData
+import org.thoughtcrime.securesms.recipients.Recipient
+import org.thoughtcrime.securesms.sms.MessageSender
+import kotlin.time.Duration.Companion.days
+
+/**
+ * Only enqueued by [RetryPendingSendsJob] for messages that are pending on app launch. When this job runs, if a message is still pending
+ * then no send job happened between app launch and draining of that thread's message send job queue. Thus it should be safe
+ * to try to resend the message.
+ *
+ * Note job is in-memory only to prevent multiple instances being enqueued per message.
+ */
+class RetryPendingSendSecondCheckJob private constructor(parameters: Parameters, private val messageId: MessageId) : Job(parameters) {
+
+  companion object {
+    const val KEY = "RetryPendingSendSecondCheckJob"
+    private val TAG = Log.tag(RetryPendingSendSecondCheckJob::class)
+  }
+
+  constructor(messageId: MessageId, threadRecipient: Recipient, hasMedia: Boolean) : this(
+    parameters = Parameters.Builder()
+      .setQueue(threadRecipient.id.toQueueKey(hasMedia))
+      .setLifespan(1.days.inWholeMilliseconds)
+      .setMemoryOnly(true)
+      .build(),
+    messageId = messageId
+  )
+
+  override fun serialize(): ByteArray? = SecondRoundFixupSendJobData(messageId = messageId.id).encode()
+
+  override fun getFactoryKey(): String = KEY
+
+  override fun run(): Result {
+    val messageRecord = SignalDatabase.messages.getMessageRecord(messageId.id)
+
+    if (!messageRecord.isPending) {
+      return Result.success()
+    }
+
+    Log.w(TAG, "[${messageRecord.dateSent}] Still pending after queue drain, re-sending MessageId::${messageId.id}!")
+
+    MessageSender.resend(context, messageRecord)
+
+    return Result.success()
+  }
+
+  override fun onFailure() = Unit
+
+  class Factory : Job.Factory<RetryPendingSendSecondCheckJob> {
+    override fun create(parameters: Parameters, serializedData: ByteArray?): RetryPendingSendSecondCheckJob {
+      val data = SecondRoundFixupSendJobData.ADAPTER.decode(serializedData!!)
+      return RetryPendingSendSecondCheckJob(parameters, MessageId(data.messageId))
+    }
+  }
+}

app/src/main/java/org/thoughtcrime/securesms/jobs/RetryPendingSendsJob.kt

@@ -0,0 +1,72 @@
+/*
+ * Copyright 2025 Signal Messenger, LLC
+ * SPDX-License-Identifier: AGPL-3.0-only
+ */
+
+package org.thoughtcrime.securesms.jobs
+
+import org.signal.core.util.logging.Log
+import org.thoughtcrime.securesms.database.SignalDatabase
+import org.thoughtcrime.securesms.database.model.MessageId
+import org.thoughtcrime.securesms.database.model.MmsMessageRecord
+import org.thoughtcrime.securesms.dependencies.AppDependencies
+import org.thoughtcrime.securesms.jobmanager.Job
+import kotlin.time.Duration.Companion.days
+
+/**
+ * It's possible for a message to be inserted into the database but the job to send it to be lost. This
+ * job tries to catch those rare situations by finding any pending messages and enqueue a second check
+ * at the end of the thread's message sending queue.
+ *
+ * If that second job still sees the message as pending, then it will try to resend it.
+ *
+ * Note job is in-memory only as it should only run once on app launch and the job will always
+ * be last in the overall queue at time of submission.
+ */
+class RetryPendingSendsJob private constructor(parameters: Parameters) : Job(parameters) {
+
+  companion object {
+    const val KEY = "RetryPendingSendsJob"
+    private val TAG = Log.tag(RetryPendingSendsJob::class)
+
+    @JvmStatic
+    fun enqueueForAll() {
+      AppDependencies.jobManager.add(RetryPendingSendsJob())
+    }
+  }
+
+  private constructor() : this(
+    Parameters.Builder()
+      .setLifespan(1.days.inWholeMilliseconds)
+      .setMaxInstancesForFactory(1)
+      .setMemoryOnly(true)
+      .build()
+  )
+
+  override fun serialize(): ByteArray? = null
+
+  override fun getFactoryKey(): String = KEY
+
+  override fun run(): Result {
+    SignalDatabase.messages.getRecentPendingMessages().use { reader ->
+      reader.forEach { message ->
+        val threadRecipient = SignalDatabase.threads.getRecipientForThreadId(message.threadId)
+        if (threadRecipient != null) {
+          val hasMedia = (message as? MmsMessageRecord)?.slideDeck?.slides?.isNotEmpty() == true
+          Log.d(TAG, "[${message.dateSent}] Found pending message MessageId::${message.id}, enqueueing second check job")
+          AppDependencies.jobManager.add(RetryPendingSendSecondCheckJob(MessageId(message.id), threadRecipient, hasMedia))
+        }
+      }
+    }
+
+    return Result.success()
+  }
+
+  override fun onFailure() = Unit
+
+  class Factory : Job.Factory<RetryPendingSendsJob> {
+    override fun create(parameters: Parameters, serializedData: ByteArray?): RetryPendingSendsJob {
+      return RetryPendingSendsJob(parameters)
+    }
+  }
+}

app/src/main/java/org/thoughtcrime/securesms/messagedetails/MessageHeaderViewHolder.java

@@ -182,6 +182,10 @@ final class MessageHeaderViewHolder extends RecyclerView.ViewHolder implements G
 
     if (messageRecord.isPending() || messageRecord.isFailed()) {
       sentDate.setText(formatBoldString(R.string.message_details_header_sent, "-"));
+      sentDate.setOnLongClickListener(v -> {
+        copyToClipboard(String.valueOf(messageRecord.getDateSent()));
+        return true;
+      });
       receivedDate.setVisibility(View.GONE);
     } else {
       Locale           dateLocale    = Locale.getDefault();

app/src/main/protowire/JobData.proto

@@ -238,4 +238,8 @@ message BackupDeleteJobData {
 
   repeated Stage completed = 1;
   Tier tier = 2;
-}
+}
+
+message SecondRoundFixupSendJobData {
+  uint64 messageId = 1;
+}