[someotherperson]

Oh wow. I did the same thing a couple of weeks ago. The server hadn't been updated since ~2015, running a blog on Ghost from that time with node 0.10 installed.

I was a bit rougher though: I just took a backup, then let my Hermes agent (Gemini 3.1 Pro) loose on it. It upgraded everything that needed to be upgraded, patched what needed to be patched, then proceeded to migrate everything to it's most recent equivalents. After that, a fair bit of server hardening was carried out followed by debloating of unused services. Likely would have continued to procrastinate doing this if it wasn't for AI support.

[Gigachad]

I mean you can update trivially without AI. The problem is the risk of breaking something, which the backup mitigates.