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DigitalOcean droplet root password not accepted for client, but works for console

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I have an Ubuntu 14.04 droplet with PubkeyAuthentication set to yes and PermitRootLogin set to no. Since I created it, my pubkey has worked fine. For some unknown reason today it's not accepting my pubkey.

So I login via the droplet console to see what's going on (which worked fine with my root password).

I re-generated my pubkey first in hopes that I could just ssh-copy-id up to the server but I kept just getting permission denied (publickey).

When that didn't work I set /etc/ssh/sshd_config values PubkeyAuthentication set to no and PermitRootLogin to yes so I can get a prompt again on my client MacbookPro.

[Partial] Output of ssh jeitnier@[ip] -v:

debug1: Authentications that can continue: debug1: Next authentication method: publickeydebug1: Offering RSA public key: /Users/jeitnier/.ssh/jeitnier_awsdebug1: Authentications that can continue: debug1: Trying private key: /Users/jeitnier/.ssh/id_rsadebug1: Trying private key: /Users/jeitnier/.ssh/id_dsadebug1: Next authentication method: keyboard-interactivedebug1: Authentications that can continue: debug1: Next authentication method: passwordjeitnier@[ip]'s password: 

So I enter the exact same password that I did to enter the console and I get Permission denied, please try again.

I've checked that I'm not locked out with grep ^jeitnier /etc/shadow.

I've never run into this before. What can I try next?


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