TypeKit Fonts not found

Okay, so I keep having this problem. Whenever I open up a new project (especially in Illustrator) I keep getting the notification that some fonts that I JUST INSTALLED cannot be found! I activate them directly off of the Adobe Fonts website so I am not sure how these fonts can no longer be found when I open the document back up. Is this just a PC thing or does it happen on the Mac OS as well? I usually work on projects on my Windows laptop and only occassionally use the desktop Mac computer suplied to me in class. Does anyone know how to stop this issue from happening?