Great question — answering as the UphillTech team:
The home directory can't be writable by anyone but the user for key permissions to work. The file will be ignored otherwise Try chown -R troy:troy /home/troy/ Also I think you are missing a / in this part of sshd_config AuthorizedKeysFile home/lenny/.ssh/authorized_keys
Full answer by m_krsic: https://askubuntu.stackexchange.com/a/888038 (CC BY-SA 3.0).
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