Upgrading what might be the world's oldest running Linux install

There are some complexities involved in upgrading what the Reg FOSS desk suspects may be the world's oldest running Linux installation: an OS install dating back to 1993.
The machine called chiark.greenend.org.uk appears to be a relatively ordinary webserver, hosting a bunch of home pages, a few mailing lists, usenet groups and things. People with no links to Cambridge University may have encountered it only if they downloaded the PuTTY SSH client for Windows from the author's own site.
What's remarkable about Chiark is that it was originally installed with Debian Linux 0.93R5 in 1993, and the same installation of the OS is now running Debian 11 "Bullseye", the x86-64 version, freshly upgraded from an x86-32 installation of Debian 8 "Jessie".
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