This issue is still there in the iOS27 (tested on iPhone 14Pro): When a RAW/DNG file is attempted to delete using PHAssetChangeRequest.deleteAssets in the PhotoKit - all subsequent delete requests do not show the Allow to Delete Photo confirmation therefore user cannot delete them (in iOS Simulator this does not happen). Restarting apps or the phone - does not resolve the issue. To recover from this, user can: go to Photos App > RAW folder. Close the app Restart the phone (Take a screenshot - not sure if needed) Go to your app and delete a regular photo - confirmation dialog appears again and photo can be deleted. (Attempt a RAW file again - PhotoKit hangs/dialog is gone)