In many cases it can be useful to know that there are small vulnerabilities everywhere if you want to maintain your anonymity and privacy to the max. That's how you can even delete the USB connection history on a system with a simple application like USBOblivion. Yes. Windows stores in its registry everything you connect, and if that bothers you, you can clear it with just two clicks.
The presumption of conspiracy behind every application that stores some data about our computer habits has reached a rather worrying level, but at the same time it has made people document themselves and learn about procedures and ways to clean up their use of computers and the internet in general. The vulnerability could be anywhere, and maybe you didn't know that Windows keeps a history of the USB devices that were connected to the system. FUUUUUUU!
Another thing you'll have to deal with, paranoid friend or amateur spy. The Windows registry keeps track of which USB devices were connected to the system and shows them to anyone who knows how to reach the key in question. So every time you plugged your phone or USB stick into a work computer, they know it. Or at least they have a way to know it.
Delete USB connection history
USBOblivion is the application you'll turn to to erase traces of your passage through that system regarding external device connections. It's absolutely free and portable software that analyzes the registry keys involved in this matter and cleans up the files, leaving everything spotless, as if nothing ever happened.
Of course, it won't just grab and wipe your registry without much caution. USBOblivion has a deletion simulation system, so it will first show you which files would be deleted and how your system would look after doing it. If you're convinced and want to proceed, check the option Do real Clean (Simulation Otherwise) and this tool will repeat the deletion of the contents of the USB connection history keys. This time, for real.
The process is quite fast and offers one more security option before permanently deleting everything: creating a backup of your .reg file. Needless to say, this is recommended, although you'd have to take that backup file and keep it with you or in a location that is not indexed and even under a different name to avoid associations. If you want to restore your USB connection history, just double-click the .reg file saved in the backup and everything will return to normal.
Remember that when using USBOblivion, the .reg file containing the USB connections becomes empty, so it would also be suspicious to a specialist on a computer that constantly has devices connected. So take the necessary precautions. USBOblivion is compatible with Windows XP, Windows 2003, Windows Vista, Windows 7, Windows 8, Windows 10 and has versions for 32 and 64 bits.