I’ve been managing keys since 1997—started on heavy iron back when “remote troubleshooting” meant driving to the data center at 2am. In that time, I’ve seen GnuPG called everything from “obsolete” to “impossible.” The truth is, most of the headaches come from treating 2026 infrastructure like it’s still 1999. People solve the same thorny problems over and over, usually by making things more complicated than they need to be. If you are still manually syncing private keys across five different laptops via USB drive, you are doing it wrong. ...

They handed you the keys and a pat on the back. “Good luck,” they said, with a look that was equal parts pity and relief. You’re the new sysadmin, the new SRE, the new DevOps guy. And you’ve just inherited a steaming pile of undocumented, unmanaged, and unstable infrastructure. Don’t panic. I’ve been there. More times than I care to count, starting from my first encounter with a closet full of overheating Sun SPARCstations in ‘98. The names change, the tech gets “better,” but the situation is always the same: you’re walking into a digital minefield. ...