"iCloud session has expired" on pc

I've seen this posted and done all the steps, nothing.

This only happens each time I restart my computer. I have to enter it 2-3 times and then it works fine.

I have iTunes match, I don't know if that makes a difference. Please let me know of any solutions. It's pretty frustrating that I need to do this at least 2-3 times every time I start up iTunes.