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.

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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

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