OK - the issue seems actually to be a lack of visual feedback when doing the image upload. There’s nothing letting me know my image has been successfully uploaded, so I’ve been closing that dialog in frustration every time. I actually got the “We are working on resolving issues” message trying to figure out if it actually took my upload this time, but turns out it did.

Now that I no longer expect it to show me that the upload has succeeded before I submit, I think I’m good.