The Draw App is saying the image has been sent, and I made sure I am signed into my account. This has worked before. Is it possible something was accidentally changed in my preferences?
A couple of things:
What version of Adobe Draw are you using?
Are you using the most recent version of Illustrator CC (v19.2.0)?
Are you signed in with the same Creative Cloud account on both the app and the desktop (many people have more than one Adobe login and it's super common to be signed in the two places with two different accounts)?