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Re: Upgrading from very-old Debian

As a friendly recommendation:
If it was about me, I would encourage to backup the home directories as well as mail or similar, depending what other kind of services running under the particular system.

Backup the data to an external usb drive or the whole source drive if you are keen on that, for example. Then do a "clean" install of a new system on the original drive. Otherwise you might run into issues, where you might miss out on an important package, if you snapshot upgrade one by one.

​I agree here.  Forget about rummaging through the last 5 years of Icelandic telephone directories; phooey to creating a cyclical re-run of the monolith scene from 2001 space odyssey, let the romantic notion of upgrading from the operating system of an ancient Egyptian abacus to a yet to be constructed quantum computer wither and fade away............

And back up your work files etc and

reinstall stretch "Jessieson"

​and sing the title track song from the sound of music NOT the one about climbing every mountain etc.

​Why bother?