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It is most likely the USB Drive (pocket size - small) is not getting enough power. Most USB 2.5" hard drives require around 1amp to function correctly. USB ports only allow 1A MAX.
What is probably happening, is due to the long wire, there is a high resistance in the cable, which is most likely causing the voltage to drop. I would suggest getting a better USB extension cable that uses a better guage of wires, if not get a powered USB hub, attach a 5v PSU to it and it should theoretically be fine.
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