Thanks for your responses!
Would you be talking about Cakewalk support, Pwalpwal?
Scook, as far as I can tell, everything is still configured correctly in my preferences.
I did try another project just to see if the problem persists, and to my surprise it doesn't. It appears this issue is with one project only.
EDIT: Hm, and the plot thickens! It's not the project as a whole, only certain parts of the project. By that I mean, say, minute one plays fine, but once it gets to minute two, it just stops working. Also of note is that I can only play it if I start it from the beginning, and not in an intermediary place.
EDIT 2: Lowering my buffers seems to have resolved the issue, fortunately!