Pub key authentication, Putty, Password authentication

Riddle me this:

I have spent the last 2.3 hours trying to figure this out. I am actually losing my mind, any help is greatly appreciated.

When creating my droplet I decided to use pub key authentication. I manage to ssh, it works great.

I have a friend who wants to ssh through Putty, but it is not working. We have converted private key into format that Putty supports but it would always return error: SSH Public Key - No supported authentication methods available

After some time I decided to just disable Pubkey authentication and enable password only. So I went to sshd config, set pubkeyauthentication to no and passwordauthentication to yes and restarted my ssh. Now when I try to login, it asks for password and then refuses it even though its correct. And when my friend tries to login it, as soon as he enters username it says No supported authentication methods available.