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I can connect to SSH just fine using the generated keys for my main user (pi) but whenever I try to connect using a different user name I've created it returns "No supported authentication methods available (server sent publickey)"

I'm stumped why it doesn't work when I change user names. Could it be a permission problem of some sort?

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the problem might be you have disabled password authentication, therefore your new users cannot log in. please, check your /etc/ssh/sshd_config for

PasswordAuthentication no

change it to yes and then

sudo /etc/init.d/ssh reload
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Have you added the public key to authorized_keys file for the second user you are trying to log in with?

So for example:

Let's assume you log into your RPi remotely from another machine's terminal window. Let's also assume you generated your RSA key on that machine and copied the public key into

/home/pi/.ssh/authorized_keys 

on your RPi.

You normally log in as pi and inside the .ssh/authoriuzed_key file is the public key you generated on the second machine so can log in without a password prompt.

If you now want to log in as "user2" to the same RPi, you will need to add the public key to

/home/user2/.ssh/authorized_keys

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