ADE quit unexpectedly when transferring EPUB book to nook

Hello, 

I've been using ADE and EPUB books for my Nook Glow light for about a year with no real issues. I just downloaded two books from the library, which showed up in the EPUB on my Mac but when I went to transfer them to my Nook, it keeps crashing. I've unauthorized and reauthorized, redownloaded the books, and the newest edition of ADE but is still keeps crashing. I've restarted the laptop as a whole as well. What is going on and can anyone help me?