Confirming on Ringtail as well.

Solution: make sure you have a public key file in ~/.ssh

Create it with ssh-keygen -y from your private key if you don't have the
public key in a separate file.

If key.pub is available, gnome-ssh-askpass pops up and asks for the
passphrase.

Without the key.pub, gnome-ssh-askpass doesn't pop up even though the
private key file is there.

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https://bugs.launchpad.net/bugs/1068304

Title:
  ssh not using gnome-ssh-askpass

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