I'd like to move my production website to 5.8.x in order to take advantage of some new features like scheduling posts, so I created a test environment to try out the new version first, I was previously on 5.7.5.9, so I first upgraded to 5.7.5.13 (no issues) then to the current 5.8.2.1.

I immediately noticed something odd, being that images I had uploaded were not displaying. I tried updating the theme, clearing the cache, nothing seemed to work.

Oddly if I try to edit a block, the images display, but once I save, it's an odd combo of one image showing and the others are just showing as the text.

If I upload a new image, it seems to display no problem, but it would be a lot of work to save every image on my existing website and re-upload it, so I'd like to find a way to fix this without going to that extreme. Has anybody else encountered this behavior?

I've attached screenshots showing how it should look, how it looks in edit mode, and how it saves.