I attempted to reproduce this. Turns out it is not so easy, with stuff
moved from archive.ubuntu.com to old-releases.ubuntu.com, and update-
manager telling me at every turn to upgrade to a newer release without
giving me the opportunity to do so.

>From what I can read from the current source code, update-manager
doesn't upgrade the system to current pacakges in the current release
before dist-upgrading. I'm not sure it should: while doing so is often
sensible, sometimes it requires upgrading things like the kernel, which
result in a need to reboot, and all this makes the dist-upgrade
experience less smooth.

Do we really need to push users to upgrade before dist-upgrading? Are
there frequent problems if they don't do that?

We already push people to upgrade pretty frequently, so most people,
most of the time, should have nothing to upgrade to, anyway. And the
rest probably don't want to.

-- 
[dist-upgrader] User should be prompted to update *before* the upgrade process 
starts
https://bugs.launchpad.net/bugs/46758
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