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 77fcb0a555..97306b797b 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
@@ -106,6 +106,8 @@ import org.thoughtcrime.securesms.groups.GroupId
 import org.thoughtcrime.securesms.jobmanager.Job
 import org.thoughtcrime.securesms.jobmanager.impl.DataRestoreConstraint
 import org.thoughtcrime.securesms.jobs.ArchiveAttachmentBackfillJob
+import org.thoughtcrime.securesms.jobs.ArchiveThumbnailBackfillJob
+import org.thoughtcrime.securesms.jobs.ArchiveThumbnailUploadJob
 import org.thoughtcrime.securesms.jobs.AvatarGroupsV2DownloadJob
 import org.thoughtcrime.securesms.jobs.BackupDeleteJob
 import org.thoughtcrime.securesms.jobs.BackupMessagesJob
@@ -594,6 +596,7 @@ object BackupRepository {
     }
 
     if (SignalStore.backup.archiveUploadState?.backupPhase == ArchiveUploadProgressState.BackupPhase.Message && AppDependencies.jobManager.find { it.factoryKey == BackupMessagesJob.KEY }.isEmpty()) {
+      Log.w(TAG, "Found a situation where message backup was in progress, but there's no active BackupMessageJob! Re-enqueueing.")
       SignalStore.backup.archiveUploadState = null
       BackupMessagesJob.enqueue()
       return
@@ -605,11 +608,18 @@ object BackupRepository {
 
     if (!AppDependencies.jobManager.areQueuesEmpty(UploadAttachmentToArchiveJob.QUEUES)) {
       if (SignalStore.backup.archiveUploadState?.state == ArchiveUploadProgressState.State.None) {
+        Log.w(TAG, "Found a situation where attachment uploads are in progress, but the progress state was None! Fixing.")
         ArchiveUploadProgress.onAttachmentSectionStarted(SignalDatabase.attachments.getPendingArchiveUploadBytes())
       }
       return
     }
 
+    if (AppDependencies.jobManager.areQueuesEmpty(ArchiveThumbnailUploadJob.QUEUES) && SignalDatabase.attachments.areAnyThumbnailsPendingUpload()) {
+      Log.w(TAG, "Found a situation where there's no thumbnail jobs in progress, but thumbnails are in the pending upload state! Clearing the pending state and re-enqueueing.")
+      SignalDatabase.attachments.clearArchiveThumbnailTransferStateForInProgressItems()
+      AppDependencies.jobManager.add(ArchiveThumbnailBackfillJob())
+    }
+
     val pendingBytes = SignalDatabase.attachments.getPendingArchiveUploadBytes()
     if (pendingBytes == 0L) {
       return
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 18b088692b..8bc36d7902 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
@@ -1105,6 +1105,17 @@ class AttachmentTable(
       .run()
   }
 
+  /**
+   * Resets the [ARCHIVE_THUMBNAIL_TRANSFER_STATE] of any attachments that are currently in-progress of uploading.
+   */
+  fun clearArchiveThumbnailTransferStateForInProgressItems(): Int {
+    return writableDatabase
+      .update(TABLE_NAME)
+      .values(ARCHIVE_THUMBNAIL_TRANSFER_STATE to ArchiveTransferState.NONE.value)
+      .where("$ARCHIVE_THUMBNAIL_TRANSFER_STATE  = ?", ArchiveTransferState.UPLOAD_IN_PROGRESS.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.
@@ -1177,6 +1188,13 @@ class AttachmentTable(
       .readToSingleLong()
   }
 
+  fun areAnyThumbnailsPendingUpload(): Boolean {
+    return readableDatabase
+      .exists(TABLE_NAME)
+      .where("$ARCHIVE_THUMBNAIL_TRANSFER_STATE = ?", ArchiveTransferState.UPLOAD_IN_PROGRESS.value)
+      .run()
+  }
+
   /**
    * Clears out the incrementalMac for the specified [attachmentId], as well as any other attachments that share the same ([remoteKey], [plaintextHash]) pair (if present).
    */