Windows: If you know you need to be more diligent about backing up your flash drive but you never get around to it, USBFlashCopy makes it simple with automatic backups every time you plug your flash drive in.
Every time you plug a new flash drive into your computer, USBFlashCopy identifies it and asks you if you want to make a new profile, use the default profile, or never back up the contents of the flash drive. If you click "new profile", you're given an array of options, like where you want the files backed up to, what to call the backup, copy speed, and filters to ignore file types. From then on, whenever you plug that device in, USBFlashCopy will scan it and start downloading the new files — copying or overwriting to the backup, per your instructions.
USBFlashCopy is free and works wherever Windows does. The purchase of a $US39.95 licence enables Silent Mode — instead of the indicator you see in the screenshot above, USBFlashCopy will copy silently in the background — but no other functionality is restricted in the free version. For an alternative application, although not automated like USBFlashCopy, check out previously reviewed USB Flash Drive Manager. Have a favourite tool for backing up your flash drives? Let's hear about it in the comments.