iTunes won't connect to iTunes Music/Store/Match
Frequently (i.e. more than a few times) I will arrive at work in the morning to find that iTunes doesn't work (all other services on my Mac seem perfectly functional). All my music on the cloud is greyed out. I can restart iTunes as much as I want, it just won't connect (and nothing in the software UI indicates it is even attempting to connect to something), raising no errors etc.
Attempting to connect to iTunes music also just does nothing (no error, no indication of attempts to connect).
The only solution, each time, is to reboot my machine, after which iTunes will work just fine for a period of a day or two.
How would I go about troubleshooting this problem? Specifically, in case it is a problem with my workplace network configuration, how would I obtain the most informative error message relating to iTunes' failure to connect, so that I can relay it to our local tech support?