diff --git a/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java b/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java
index 4682f5ec69..20cfdb8a91 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java
@@ -205,6 +205,7 @@ public class ApplicationContext extends Application implements AppForegroundObse
               .addNonBlocking(AppDependencies::getBillingApi)
               .addNonBlocking(this::ensureProfileUploaded)
               .addNonBlocking(() -> AppDependencies.getExpireStoriesManager().scheduleIfNecessary())
+              .addNonBlocking(BackupRepository::maybeFixAnyDanglingAttachmentUploads)
               .addPostRender(() -> AppDependencies.getDeletedCallEventManager().scheduleIfNecessary())
               .addPostRender(() -> RateLimitUtil.retryAllRateLimitedMessages(this))
               .addPostRender(this::initializeExpiringMessageManager)
diff --git a/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt b/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt
index 80013b7ad7..8c6ae86664 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt
@@ -100,6 +100,7 @@ import org.thoughtcrime.securesms.jobmanager.Job
 import org.thoughtcrime.securesms.jobmanager.impl.DataRestoreConstraint
 import org.thoughtcrime.securesms.jobmanager.impl.NetworkConstraint
 import org.thoughtcrime.securesms.jobmanager.impl.WifiConstraint
+import org.thoughtcrime.securesms.jobs.ArchiveAttachmentBackfillJob
 import org.thoughtcrime.securesms.jobs.AvatarGroupsV2DownloadJob
 import org.thoughtcrime.securesms.jobs.BackupDeleteJob
 import org.thoughtcrime.securesms.jobs.BackupMessagesJob
@@ -112,6 +113,7 @@ import org.thoughtcrime.securesms.jobs.RestoreAttachmentJob
 import org.thoughtcrime.securesms.jobs.RestoreOptimizedMediaJob
 import org.thoughtcrime.securesms.jobs.RetrieveProfileJob
 import org.thoughtcrime.securesms.jobs.StickerPackDownloadJob
+import org.thoughtcrime.securesms.jobs.UploadAttachmentToArchiveJob
 import org.thoughtcrime.securesms.keyvalue.BackupValues.ArchiveServiceCredentials
 import org.thoughtcrime.securesms.keyvalue.KeyValueStore
 import org.thoughtcrime.securesms.keyvalue.SignalStore
@@ -613,6 +615,23 @@ object BackupRepository {
     SignalStore.backup.snoozeDownloadNotifier()
   }
 
+  @JvmStatic
+  fun maybeFixAnyDanglingAttachmentUploads() {
+    if (!SignalStore.backup.backsUpMedia || !AppDependencies.jobManager.areQueuesEmpty(UploadAttachmentToArchiveJob.QUEUES)) {
+      return
+    }
+
+    val pendingBytes = SignalDatabase.attachments.getPendingArchiveUploadBytes()
+    if (pendingBytes == 0L) {
+      return
+    }
+
+    Log.w(TAG, "There are ${pendingBytes.bytes.toUnitString(maxPlaces = 2)} of attachments that need to be uploaded to the archive, but no jobs for them! Attempting to fix.")
+    val resetCount = SignalDatabase.attachments.clearArchiveTransferStateForInProgressItems()
+    Log.w(TAG, "Cleared the archive transfer state of $resetCount attachments.")
+    AppDependencies.jobManager.add(ArchiveAttachmentBackfillJob())
+  }
+
   /**
    * Whether or not the "Your media will be deleted today" sheet should be displayed.
    */
diff --git a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/remote/RemoteBackupsSettingsViewModel.kt b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/remote/RemoteBackupsSettingsViewModel.kt
index c45ca1df8e..f9dc3ebbd3 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/remote/RemoteBackupsSettingsViewModel.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/remote/RemoteBackupsSettingsViewModel.kt
@@ -164,6 +164,10 @@ class RemoteBackupsSettingsViewModel : ViewModel() {
         }
       }
     }
+
+    viewModelScope.launch(Dispatchers.IO) {
+      BackupRepository.maybeFixAnyDanglingAttachmentUploads()
+    }
   }
 
   fun setCanBackUpUsingCellular(canBackUpUsingCellular: Boolean) {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
index fdca9a6eae..0a880ecb1e 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
@@ -868,6 +868,17 @@ class AttachmentTable(
     }
   }
 
+  /**
+   * Resets the [ARCHIVE_TRANSFER_STATE] of any attachments that are currently in-progress of uploading.
+   */
+  fun clearArchiveTransferStateForInProgressItems(): Int {
+    return writableDatabase
+      .update(TABLE_NAME)
+      .values(ARCHIVE_TRANSFER_STATE to ArchiveTransferState.NONE.value)
+      .where("$ARCHIVE_TRANSFER_STATE IN (${ArchiveTransferState.UPLOAD_IN_PROGRESS.value}, ${ArchiveTransferState.COPY_PENDING.value}, ${ArchiveTransferState.TEMPORARY_FAILURE.value})")
+      .run()
+  }
+
   /**
    * Marks eligible attachments as offloaded based on their received at timestamp, their last restore time,
    * presence of thumbnail if media, and the full file being available in the archive.