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Ubuntu 20.04 - Unable to login into GCloud via CLI SSH after Ubuntu 20.04 Upgrade

TLDR;


cp -prf ~/.ssh /tmp/.ssh_2024_02_24
chmod 700 ~/.ssh
chmod 600 ~/.ssh/*


I had this curious issue, where my perfectly fine GCloud SSH Login via CLI stopped working when I moved from Ubuntu 18 to Ubuntu 20.


The error I was was not very descriptive, even when running verbose


gcloud --project=my-project compute ssh my-server-01  --zone=asia-south1-c --internal-ip

ERROR: (gcloud.compute.ssh) [/usr/bin/ssh] exited with return code [255].


Verbose mode ( not including output for brevity ) :


gcloud --project=my-project compute ssh my-server-01  --zone=asia-south1-c --internal-ip --verbosity=debug


Now, this happened twice with me. Once when I upgraded! And second when I used a laptop freshly installed with Ubuntu 20.

The first time it happened, I assumed something broke in the upgrade and reinstalled the OS since it was already on a different partition. Still no luck. The final solution was to downgrade to Ubuntu 18.

2nd time around, I was more determined to find the cause. I figured out it was due to OpenSSH becoming more strict, but I didn't have the option to downgrade it.  I tried adding options to openssl config, hoping to use a less latest version  of TLS. Nope, no success!

And after lot of search, I ended up on a stackoverflow.com page, which mentioned that it could be a case of .ssh files not having secure permissions and the SSH error message being insufficient misleading .

So, I crossed my fingers and did as suggested,

cp -prf ~/.ssh /tmp/.ssh_2024_02_24
chmod 700 ~/.ssh
chmod 600 ~/.ssh/*

And that solved it!




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