I have an old iPod Classic that still works fine but it is having difficulty establishing a connection to my computer.  It will make an incomplete connection but it takes a long time and the computer hangs up until the connection is made. iTunes can't see

I have an old iPod Classic.  It still plays the music on it out of either port.  It is having trouble connecting to my Windows 7 (64bit) computer.   It takes about 30 seconds or more to connect and hangs the computer until it does.  Even though it shows up in connected USB devices and in Windows explorer it doesn't seem right.  Sometimes it does not make a connection and when it does make a connection iTunes cannot detect it, even though iTunes sometimes automatically launches when I plug in the iPod.  I've tried two different sets of cables with the same results.

Check the iPod Hardisk health with the iPod  Disk Diagnostic, as posted by tt2
https://discussions.apple.com/message/17776595#17776595
It wont fix your problem, but may tell help troubleshoot, why it is freezing iTunes, especially when the Pending and Realloc numbers are high.
have a nice day!

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