I upgraded the UCL CS webserver to CERN/3.0 (the last CERN httpd release) running on a Sun Sparcstation 10 back in 1994, and it has been in production use ever since. The hardware got replaced at least once (our sysadmin has a large pile of spare mid-1990s Sparc hardware), and the NFS server storing the data has changed more than once, but it's the same software install still running on 1990s Sun hardware. It needed some minor patches for Y2K, but nothing in the 24 years since. Will be 30 years this summer. Needless to say as it predates SSL, it's no longer our primary server, but it does still serve everyone's home pages.
That's so amazing. That Sun sparc 10 was a beast of a machine. I had one running until 2020. It was seemingly unstoppable. It broke my heart to send it off to recycling, it's weird being emotional about a computer. It had been serving web pages (on-and-off) since 1997.