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Ok, I've never heard of a flash drive triggering an "Insert disk into" message, since obviously you can't insert anything into a flash drive. That message CAN come up on memory card readers that present themselves essentially as a reader device that can then have actual media inserted into it (much like an optical disc drive), which is why I thought that you might in fact be working with a memory card. And flash drives can show a DIFFERENT message such as "Please format drive D", which can come up if you have an unformatted partition or a corrupted partition. But that doesn't appear to be the error you have.
So I don't know exactly what would cause that particular message with that type of device, but have you tried other USB ports on this system or even USB ports on completely different systems to see if the flash drive is similarly unreliable in allowing its contents to be accessed? Conversely, do you have other flash drives to try on that USB port? That would help isolate variables to determine where the problem lies.
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