Hey @Bryce_Alsten,
This looks like a different issue from that earlier thread, so rebuilding the bot’s computer probably won’t fix it this time. Some screenshot and file uploads from the desktop app are failing right now while text sends normally. This is an issue we’re tracking.
To confirm you’re hitting the same thing, could you share the exact message that shows above the message box when the send fails? A screenshot works great. If it says something other than “Couldn’t upload an attachment. Try again.”, let me know and I’ll take a closer look at your bot’s computer.
I’ll post here when there’s an update.