diff --git a/src/functions/backend/db/bot-files/delete-bot-file.ts b/src/functions/backend/db/bot-files/delete-bot-file.ts
index e58c32c..7700955 100644
--- a/src/functions/backend/db/bot-files/delete-bot-file.ts
+++ b/src/functions/backend/db/bot-files/delete-bot-file.ts
@@ -33,6 +33,13 @@ export default async function deleteBotFile({ scopes, file_id }: Params) {
     }
 
     await BunSQLite.sql({ sql: `DELETE FROM bot_file_vectors WHERE file_id = ?`, values: [file.id] });
+    /**
+     * Deleted here rather than left to the schema's cascade: SQLite has
+     * foreign keys off per connection unless `enableForeignKeys` ran, and
+     * a script or CLI process that deletes a file would otherwise leave
+     * its chunks behind, which then fail the next schema sync.
+     */
+    await BunSQLite.sql({ sql: `DELETE FROM bot_file_chunks WHERE file_id = ?`, values: [file.id] });
     await BunSQLite.sql({ sql: `DELETE FROM bot_files WHERE id = ?`, values: [file.id] });
     /**
      * Its pending ingestion would only find nothing left.
diff --git a/src/functions/backend/db/bot-files/purge-storage.ts b/src/functions/backend/db/bot-files/purge-storage.ts
index 5d4c91d..46d545d 100644
--- a/src/functions/backend/db/bot-files/purge-storage.ts
+++ b/src/functions/backend/db/bot-files/purge-storage.ts
@@ -59,6 +59,17 @@ export default async function purgeStorage({ scope, owner_id, media_ids }: Param
             values: [scope, owner_id],
         }).catch(() => {});
 
+        /**
+         * Deleted here rather than left to the cascade, since SQLite has
+         * foreign keys off per connection unless `enableForeignKeys` ran (a
+         * script or CLI process never does), and a chunk left behind fails
+         * the next schema sync.
+         */
+        await BunSQLite.sql({
+            sql: `DELETE FROM bot_file_chunks WHERE scope = ? AND owner_id = ?`,
+            values: [scope, owner_id],
+        }).catch(() => {});
+
         /**
          * Usually gone already, with the bot or workspace (the cascade).
          */