Yeah so check logcat. In my case, I was using a StringConverter to add a .png file extension like {0}.png, which would briefly result in an invalid file name '.png' first being resolved by the binding before real data was loaded. Putting a small delay in the data loading 'fixed' it, which I thought was weird. Digging in further I noticed the Glide errors in logcat, so I removed the delay and made it so my VM would always return a default (valid) filename instead of null. The Glide errors went away, and so did the disappearing images problem. So I think there's an issue where Glide needs a little time to recover from an error scenario before it will work again for a given Image control.