Ryan

Make sure you "eject" the DMG from your finder sidebar after you make changes, otherwise the background image won't update

Sure, but it may be better to add a better check here instead, I wrote an old S3 module for SS2.4 which checked the headers were 200 on S3 files...

Another issue I saw was that when my app auto scales or I deploy, the cached images are of course lost, but the DB CloudImageCachedStore still tells SilverStripe they exist,...

I had this on all uploads in my site, I couldn't figure it out, so I just changed all instances of: static $has_one = array( "Image" => "Image" ); to:...

@joeherbert which version of SS are you using?

@joeherbert I think in the end I rolled back to a previous version.... there were too many problems otherwise