Typekit desktop sync removes rather then adding font

I am encountering a very strange problem.

I had used typekit desktop sync which worked fine. In the middle of creating a document the font suddenly stopped working. As I try to work through this problem, I notice when I try to readd the font (after removing it) it consistently says "5 font files have been removed" even though I just selected them to sync to the desktop.

Instead of adding them when desktop syncing is selected, it removes them (even though they were never present). It is very strange and I could not find a topic relating to this.

Any ideas?