Microsoft released a diagnostics tool to help them help you with problems. If you want to see it failing to run on my Windows XP, you can just click "read more". When will you release a diagnostics tool for the diagnostics tool ? ...
In my case it diagnosed it can diagnose anything:
ClicZune on the other hand was more lucky:
What you can do with it:
1. Open the Zune software.Boring stuff for people with Zune problems!
2. Run the ZuneDevices.exe tool.
3. Connect the device and wait for any errors to be displayed.
3a. For USB connections, look for the device to appear in device manager under portable devices. There may be a yellow exclamation mark next to the device.
3b. For wireless connections, use Settings->Wireless->Sync Now on the device and wait for the device to display an error, usually one to two minutes after displaying “Connecting to PC”.
4. Disconnect the device. For wireless connections, click the Cancel or Ok button.
5. Click on the Report tab of the tool, then click “Save As” and save a copy of the report text for analysis.
6. Send the report text file to Product Support Services.
Links:
Zune Devices Diagnostics Tool