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Summary: When iTunes Match is used on a OS X 10.8.x machine, it fails to upload new songs.

Steps to Reproduce: iTunes Match is just activated for the first time. iTunes will scan all songs. If iTunes cannot match some of the songs, it will require uploading them to benefit from the service. Following the screenshots attached, iTunes Match gathers information from the library in question, then matches it with the iTunes Store. Upon the upload artwork and songs, the service will hang and stop.

Expected Results: iTunes Match will upload required songs and finish the upload/updating process.

Actual Results: iTunes Match hangs and requires you to start the process over again. Once you try again, same results occur. Stuck in a loop.

Regression: This issue only occurs on certain Wi-Fis. When using the Wi-Fi in an Apple Store, issue is non-existent.

Notes: I've had this issue occurs since upgrading to Mountain Lion. I thought it was a bad build originally, but as the time progressed, multiple iTunes and OS X updates were released and the issue is still existent.

This thread on Apple Discussions summarizes the issue, and how widespread it is.