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I've never been able to connect to pythonanywhere via SSH even after switching to a paid plan, I added my public key to ~/.ssh/authorized_keys but still nothing.

When I try to connect using the command: ssh steinitzu@ssh.pythonanywhere.com
I get back (without being prompted for a password):
<<<<<<:>~ PythonAnywhere SSH. Help @ https://www.pythonanywhere.com/wiki/SSHAccess Permission denied (publickey,password).

Wondering if it's a failure on my end or if my ssh access failed to get activated for some reason?

Thanks

That without being prompted for a password part sounds very weird- that definitely should not happen.

Running ssh steinitzu@ssh.pythonanywhere.com on my machine now prompts for a password. Are you using a normal bash shell when running the command?

My bad!
Turns out I had disabled password authentication in my global ssh_config at some time in the past and totally forgot about it. Removed that line and immediately got in with my PA password.
Looks like I also managed to botch my public key when copying it in, cause I erased and copied it over again and now everything works as it should. :)

Excellent, glad you managed to sort it out :-)