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Long story short, one of my machines hasn't been updated for a while, and the gpg keys it has for key servers and apt repositories have all expired. If possible, I would like to restore them to a usable state securely, without simply telling it to use an unverified key.

I have access to other machines that are properly updated, so I should theoretically be able to use one of them to get the necessary keys; however, despite much Googling and consternation, I have not been able to figure out how to do this.

The machine in question runs Debian.

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If you've got another Debian machine you trust which has a current keyset, export them all and import them in your new machine.

On your up to date machine, run

gpg -a --export >keyring.asc

On the old machine, do

gpg --import <keyring.asc

This will add all public keys with their web of trust to the old computer.

If you trust the (SSL encrypted) Debian website, you could also download the key archive from there and import the keys.

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When I did the import, gpg spat out the mysterious warning "no ultimately trusted keys found", but it seems to be working now despite that. – user142088 Jul 11 '13 at 21:38
It turns out that Debian also has the key archive available over SSL. – user142088 Jul 11 '13 at 21:39
Good point, didn't expect that the package page wasn't encrypted. Updates to the key archive page which is more convenient anyway. – Jens Erat Jul 12 '13 at 7:31

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