Windows 10, and this was happening in Chrome, Firefox, and Edge on two separate computers on two separate wifis. Something's weird :P

I'll try a different account tommorow and see if that works

Yeah I could reproduce the issue when I first upload images, and edit titles.
When I edit titles first, then upload images, it seems okay.

I'll fix it as soon as possible.
Thanks for your report again! :)

hum.. I'll test it again on Windows 10 again.
Thanks for your report :)

I think I just fixed the issue. Can you try again?

The image disappearing problem is gone but the post button is still grayed out and the preview doesn't show an image :/

hum.. I just tested on Windows 10 with Chrome and Edge and it seems it working for me.
Can you give me the image you used?

Here's a link to it:

If it's not working on your end I'll just decide it's my crazy computer and try it on one of my school's computers.

Not working on a school computer either :P Does it upload images to Imgur by any chance?

Humm.. yes we upload photos to Imgur. Do you have any network blocking setups with Imgur?

Yep, that's it :P School blocks it and my computer was to for some reason (facepalm) Thanks for the help