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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https://bugs.launchpad.net/bugs/1764044

Title:
  ssh-add asks about passphrases for keys already unlocked in the
  keychain

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