We just spend some time on #ubuntu-bugs triaging this one and this is
what we found out.

For some time the agent responsible for caching ssh passwords is Gnome
Keyring and dialog is displayed by gnome-keyring-prompt. Gnome Keyring,
as stated on its website supports both SSH v1 and SSH v2 protocols but
former only in compatibility mode. In this mode Gnome Keyring still
caches keys but they have to be added using ssh-add.

At least in David's case we have managed to track the issue down to his
old DSA key, he has reported that a newly generated RSA key works as
expected - i.e. password prompt shows up. I've also confirmed that it
shows up for newly generated DSA keys.

To all who are affected by this bug can you confirm that generating a
new key solves the issue?

I'm also reassigning package to gnome-keyring as ssh-askpass-gnome isn't
used anymore.

** Package changed: openssh (Ubuntu) => gnome-keyring (Ubuntu)

** Changed in: gnome-keyring (Ubuntu)
       Status: Confirmed => Incomplete

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ssh-askpass-gnome doesn't prompt for password in any release post ubuntu 8.10 
32/64bit
https://bugs.launchpad.net/bugs/578035
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