This was happening to me for awhile, I typically used USB key's for music and one was acting up...then ipod wasn't working either.
I cleaned the port and used a different cable, problemed solved.
Hope thats all it is for you otherwise perhaps the cable was being pulled at times and bent the port a bit...
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2017 SUBARU STI
2008 E60 M5 - SOLD
2010 40th Anniversary 370Z - SOLD (and missing her)
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