diff --git a/db/post_migrate/20231127165331_trigger_auto_linking_for_videos_since_placeholder.rb b/db/post_migrate/20231127165331_trigger_auto_linking_for_videos_since_placeholder.rb
new file mode 100644
index 00000000000..82c85041179
--- /dev/null
+++ b/db/post_migrate/20231127165331_trigger_auto_linking_for_videos_since_placeholder.rb
@@ -0,0 +1,36 @@
+# frozen_string_literal: true
+
+class TriggerAutoLinkingForVideosSincePlaceholder < ActiveRecord::Migration[7.0]
+  disable_ddl_transaction!
+
+  def up
+    # Rebake any existing video placeholder posts to ensure they are auto-linked
+    # to post uploads
+    max_id = DB.query_single(<<~SQL).first.to_i
+      SELECT MAX(id)
+      FROM posts
+    SQL
+
+    chunk_size = 100_000
+    while max_id > 0
+      ids = DB.query_single(<<~SQL, start: max_id - chunk_size, finish: max_id)
+        SELECT id
+        FROM posts
+        WHERE cooked LIKE '%video-placeholder-container%'
+        AND id > :start AND id <= :finish
+      SQL
+
+      DB.exec(<<~SQL, ids: ids) if ids && ids.length > 0
+          UPDATE posts
+          SET baked_version = NULL
+          WHERE id IN (:ids)
+        SQL
+
+      max_id -= chunk_size
+    end
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+end