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I don't know anything about wince, but we tried USB hard drives on another product of ours and discovered a couple of things to check. First, if the drive is port powered make sure it doesn't exceed the USB port power that is available. Second, it seems that sometimes hard drives seem slow to enumerate. Maybe they don't enumerate until they spin up and by that time the enumeration process has failed from the host perspective. We found that USB micro-drives generally worked and the full size drives in external housings often failed. YMMV.
I don't know anything about wince, but we tried USB hard drives on another product of ours and discovered a couple of things to check. First, if the drive is port powered make sure it doesn't exceed the USB port power that is available. Second, it seems that sometimes hard drives seem slow to enumerate. Maybe they don't enumerate until they spin up and by that time the enumeration process has failed from the host perspective. We found that USB micro-drives generally worked and the full size drives in external housings often failed. YMMV.