It's possible to do this in a way that doesn't reveal your IP - run the update-checking server as a Tor onion service and embed a little client that knows how t

It's possible to do this in a way that doesn't reveal your IP - run the update-checking server as a Tor onion service and embed a little client that knows how to connect to the Tor network. Then your entry node doesn't know what you're connecting to, and the remote update server only knows the IP of the relay talking to it, not your actual IP. Still, a good question is how you're getting updates in the absence of automatic updates (and for software whose goal is parsing binary file formats, chances are high that if you aren't getting updates, you have a pretty big privacy problem already). If you have no auto-update code but you're telling users to download new versions from, say, GitHub, then GitHub gets their IP addresses anyway.