Ive noticed sometimes if I get a 'failed to deliver" message from sending an image directly from the Photos app,yet it does not happen from the messages app, my iPad was fine untill I updated to 16.1 I don't use iCloud either because I dont want to so lets get that out of the way, but if you have a iMessage from the person either in your inbox or in your deleted folder it works fine from the photos App, anyone else seen this? My ipad was fine on 15.7 then this started when I updated just like my iPhone 14 Pro has this issue too. So its not a phone/iPad issues its a iOS 16/16.1/16.1.1 issue it seems.