I finally was able to solve this. It turns out, my key was too old and thus kind of disabled as a security measure, I suppose. After creating a new key based off ED25519 and adding the corresponding public key to ~/.ssh/authorized_keys on the server, things are now working again.
Can we please do better and inform the user what's wrong instead of silently pretending to be working but dropping the unlocked key? FWIW, even now with the process working again "keychain -l" still lists nothing. I'm not 100% sure but that looks like a bug of its own. -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to openssh in Ubuntu. https://bugs.launchpad.net/bugs/1764044 Title: ssh-add asks about passphrases for keys already unlocked in the keychain Status in openssh package in Ubuntu: New Bug description: In the below example, on the second invocation of ssh-add I should not be prompted to enter the passphrase again after I successfully entered it on the first instance. This used to work fine in trusty i386 setup. $ keychain && ssh-add * keychain 2.8.2 ~ http://www.funtoo.org * Starting ssh-agent... Enter passphrase for /home/rolf/.ssh/id_rsa: Identity added: /home/rolf/.ssh/id_rsa (/home/rolf/.ssh/id_rsa) Enter passphrase for /home/rolf/.ssh/id_dsa: Identity added: /home/rolf/.ssh/id_dsa (/home/rolf/.ssh/id_dsa) $ keychain && ssh-add * keychain 2.8.2 ~ http://www.funtoo.org * Found existing ssh-agent: 25744 Enter passphrase for /home/rolf/.ssh/id_rsa: Identity added: /home/rolf/.ssh/id_rsa (/home/rolf/.ssh/id_rsa) Enter passphrase for /home/rolf/.ssh/id_dsa: Identity added: /home/rolf/.ssh/id_dsa (/home/rolf/.ssh/id_dsa) gnome-keyring is running: $ ps -ax|grep key 2067 ? SLl 0:05 /usr/bin/gnome-keyring-daemon --start --components ssh 2078 ? Ssl 0:01 /usr/lib/x86_64-linux-gnu/indicator-keyboard/indicator-keyboard-service --use-gtk 6987 ? S 0:00 /usr/bin/ssh-agent -D -a /run/user/1000/keyring/.ssh 17832 pts/2 S+ 0:00 grep --color=auto key ssh-agent is running: $ ps aux | grep ssh-agent leggewie 1928 0.0 0.0 15548 340 ? Ss 02:38 0:00 /usr/bin/ssh-agent /usr/bin/im-launch env LD_PRELOAD=libgtk3-nocsd.so.0 /usr/lib/gnome-session/run-systemd-session unity-session.target leggewie 6987 0.0 0.0 11304 1484 ? S 02:50 0:00 /usr/bin/ssh-agent -D -a /run/user/1000/keyring/.ssh leggewie 9952 0.0 0.0 11304 320 ? Ss 04:11 0:00 ssh-agent bash leggewie 17850 0.0 0.0 14492 1160 pts/2 S+ 06:06 0:00 grep --color=auto ssh-agent $ env|grep SSH SSH_AUTH_SOCK=/tmp/ssh-W6fuGBztRRds/agent.6992 SSH_AGENT_PID=9952 SSH_AGENT_LAUNCHER=gnome-keyring To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1764044/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp