one of the most annoying bugs i've noticed about iTunes Match, often times, if i open up iTunes, my iCloud music library will be stuck on a loop (meaning it's not connected to iCloud). the library will be usable, but i'm not able to upload/download anything from the cloud. the only way to resolve it is to quit iTunes, open it again, and sometimes it still doesn't connect. i don't know if it's my network settings, my library size (i have 22k+ songs in my library) or just a bug, but it happens more frequently than not. usually, after i have iTunes closed for a while and re-open, it will go into the loop state.
this image show's the icon i'm talking about
and when it connects, the cloud becomes solid gray.
this image show's the icon i'm talking about
and when it connects, the cloud becomes solid gray.