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 7fd3af1023..21160cc79f 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
@@ -724,7 +724,7 @@ class AttachmentTable(
         $ARCHIVE_TRANSFER_STATE = ${ArchiveTransferState.NONE.value} AND
         $DATA_FILE NOT NULL AND
         $TRANSFER_STATE = $TRANSFER_PROGRESS_DONE AND
-        $REMOTE_KEY IS NULL
+        ($REMOTE_KEY IS NULL OR LENGTH($REMOTE_KEY) = 0)
         """
       )
       .run()
@@ -1845,13 +1845,11 @@ class AttachmentTable(
   fun createRemoteKeyIfNecessary(attachmentId: AttachmentId) {
     val key = Util.getSecretBytes(64)
 
-    writableDatabase.withinTransaction {
-      writableDatabase
-        .update(TABLE_NAME)
-        .values(REMOTE_KEY to Base64.encodeWithPadding(key))
-        .where("$ID = ? AND $REMOTE_KEY IS NULL", attachmentId.id)
-        .run()
-    }
+    writableDatabase
+      .update(TABLE_NAME)
+      .values(REMOTE_KEY to Base64.encodeWithPadding(key))
+      .where("$ID = ? AND ($REMOTE_KEY IS NULL OR LENGTH($REMOTE_KEY) = 0)", attachmentId.id)
+      .run()
   }
 
   /**
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/helpers/SignalDatabaseMigrations.kt b/app/src/main/java/org/thoughtcrime/securesms/database/helpers/SignalDatabaseMigrations.kt
index 2de459e87e..b590f0ceff 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/helpers/SignalDatabaseMigrations.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/helpers/SignalDatabaseMigrations.kt
@@ -145,6 +145,7 @@ import org.thoughtcrime.securesms.database.helpers.migration.V287_FixInvalidArch
 import org.thoughtcrime.securesms.database.helpers.migration.V288_CopyStickerDataHashStartToEnd
 import org.thoughtcrime.securesms.database.helpers.migration.V289_AddQuoteTargetContentTypeColumn
 import org.thoughtcrime.securesms.database.helpers.migration.V290_AddArchiveThumbnailTransferStateColumn
+import org.thoughtcrime.securesms.database.helpers.migration.V291_NullOutRemoteKeyIfEmpty
 import org.thoughtcrime.securesms.database.SQLiteDatabase as SignalSqliteDatabase
 
 /**
@@ -295,10 +296,11 @@ object SignalDatabaseMigrations {
     287 to V287_FixInvalidArchiveState,
     288 to V288_CopyStickerDataHashStartToEnd,
     289 to V289_AddQuoteTargetContentTypeColumn,
-    290 to V290_AddArchiveThumbnailTransferStateColumn
+    290 to V290_AddArchiveThumbnailTransferStateColumn,
+    291 to V291_NullOutRemoteKeyIfEmpty
   )
 
-  const val DATABASE_VERSION = 290
+  const val DATABASE_VERSION = 291
 
   @JvmStatic
   fun migrate(context: Application, db: SignalSqliteDatabase, oldVersion: Int, newVersion: Int) {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/helpers/migration/V291_NullOutRemoteKeyIfEmpty.kt b/app/src/main/java/org/thoughtcrime/securesms/database/helpers/migration/V291_NullOutRemoteKeyIfEmpty.kt
new file mode 100644
index 0000000000..ed26344c61
--- /dev/null
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/helpers/migration/V291_NullOutRemoteKeyIfEmpty.kt
@@ -0,0 +1,19 @@
+/*
+ * Copyright 2024 Signal Messenger, LLC
+ * SPDX-License-Identifier: AGPL-3.0-only
+ */
+
+package org.thoughtcrime.securesms.database.helpers.migration
+
+import android.app.Application
+import org.thoughtcrime.securesms.database.SQLiteDatabase
+
+/**
+ * If remote_key is an empty byte array (base64 encoded), replace with null.
+ */
+@Suppress("ClassName")
+object V291_NullOutRemoteKeyIfEmpty : SignalDatabaseMigration {
+  override fun migrate(context: Application, db: SQLiteDatabase, oldVersion: Int, newVersion: Int) {
+    db.execSQL("UPDATE attachment SET remote_key = NULL WHERE remote_key IS NOT NULL AND LENGTH(remote_key) = 0")
+  }
+}
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/UploadAttachmentToArchiveJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/UploadAttachmentToArchiveJob.kt
index 8b1aa4f005..256a2e179a 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/UploadAttachmentToArchiveJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/UploadAttachmentToArchiveJob.kt
@@ -166,7 +166,7 @@ class UploadAttachmentToArchiveJob private constructor(
       return Result.success()
     }
 
-    if (attachment.remoteKey == null) {
+    if (attachment.remoteKey == null || attachment.remoteKey.isBlank()) {
       Log.w(TAG, "[$attachmentId] Attachment is missing remote key! Cannot upload.")
       return Result.failure()
     }