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I've followed the tutorial from Debian (which is virtually identical to the one from Canonical) on how to set up unattended-upgrades, on an 18.04 server VM. I primarily want this for email update notifications, as a "set it and forget it" kind of thing. But when I do a dry-run of unattended-upgrade, I don't get an email notification. I read somewhere that some versions of unattended-upgrades don't send the email on a dry run.

How can I temporarily install an "old" package, and then let unattended-upgrades actually have something to upgrade? That seems like the most reliable way to test it.

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Slightly different from what you are asking, but should accomplish the same thing:

Add a PPA that has a newer version of an installed package:

sudo apt install certbot
sudo add-apt-repository ppa:certbot/certbot

See if unattended-upgrades updates the package.

I haven't tested this, so it's possible there is something about certbot that makes it not a good PPA to use. Others to try might include nginx and the PPA from ppa:nginx/stable.

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    The default setting for Unattended Upgrades is to ONLY upgrade packages in the -security pocket of the Ubuntu repos. To be more useful, answer should include how to add the PPA to that Unattended Upgrades setting...and then how to restore the stock setting after testing is complete.
    – user535733
    Jul 21, 2021 at 1:35

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