What Makes a USB Device Work Only After I Plug It In Three Times?

My USB device often fails to connect or appear in Windows the first time I plug it in, but it usually works after I unplug and reconnect it several times. What could cause this behavior, such as a loose or damaged port or cable, insufficient power, a faulty device, or driver issues, and how can I troubleshoot it? I would appreciate advice on finding the underlying cause and making the device connect reliably on the first try.