Possibly the 20.04.4 live system is also involved, because to my
knowledge setting a proxy via Settings/Network does not normally make
any changes to /etc/apt/apt.conf (i.e. you are not prompted for a sudo
password after setting a manual proxy in Settings/Network).

So I'm guessing the 20.04.4 live system made the apt.conf change since
apt requires it. (Note: some earlier versions of Ubuntu live systems did
not make the apt.conf change automatically; we had to do it manually
whenever we had to use  proxies.)

In any case, whatever cleared the manual proxy setting from both user
accounts ideally shouldn't do that.

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https://bugs.launchpad.net/bugs/1986850

Title:
  Manual proxy is partially cleared on 20.04 => 22.04 upgrade

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