Is it possible to backdate an Ubuntu restore to trick an expired password prompt

Question

I use passwordless login with SSH to access my Ubuntu 18.04 DigitalOcean droplet, on which I've disabled root login, using a sudo-enabled account. I do not have a login password/sudo password. My password setting is ALL=(ALL) NOPASSWD: ALL, so that I never have to enter one.

However, I tried logging in to my droplet today and it told me my non-existent password is expired. It wants the current password to change the password. But...I don't have a current password.

As I said, the root login is disabled, so I have no other way in. I assume I'm screwed, unless you know of a way I can remotely login bypassing the expired password check.

The only other thing I can think of is if I can restore a backup of the server but backdate it during restoration by 30 days or whatever, so that it thinks my password is still valid. Is it possible to do that, even if it means only a higher level of support has to do it for me?

Not exactly sure what Digital Ocean provides but can't you reboot to a live recovery or something that allows you to access the disk? — Ginnungagap, Oct 08 '20 at 05:57
DigitalOcean provides a ["reset root password"](https://www.digitalocean.com/docs/droplets/resources/reset-root-password/) function. Did you try it? — Gerald Schneider, Oct 08 '20 at 06:29
How would resetting the root password help if root login is disabled? — selfagency, Oct 08 '20 at 13:49
disabling the root account is usually accomplished by unsetting the password. resetting it should also enable the account. Apart from that, just because root login is disabled for SSH doesn't mean it is also disabled for the local console. — Gerald Schneider, Oct 08 '20 at 13:54
@GeraldSchneider It's telling me that there's no ssh key associated with root — selfagency, Oct 08 '20 at 14:25
Everything you need is in that answer and in the documentation. Don't mind that FreeBSD is mentioned there, the procedure is the same. — Gerald Schneider, Oct 08 '20 at 14:38
@GeraldSchneider Thanks, you are my frickin' hero right now. — selfagency, Oct 08 '20 at 15:17

Is it possible to backdate an Ubuntu restore to trick an expired password prompt

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