Okay, per discussion with pitti in IRC, I think the proper solution
would involve:

 * changing the symlink in an un-mounted ~/Private directory to point
to a wrapper script, instead of /sbin/mount.ecryptfs_private
 * having that wrapper script:
   * first try to perform the mount
   * if the required key is not found
     * Explain the situation
     * Prompt for the password using gksu/zenity/kdesu
     * Perform the mount

This is Jaunty material, and will probably involve assistance from the
desktop folks.

:-Dustin

-- 
Encrypted Private Directory is not automatically mounted when using gdm 
auto-login
https://bugs.launchpad.net/bugs/284443
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Status in “ecryptfs-utils” source package in Ubuntu: Won't Fix
Status in “gdm” source package in Ubuntu: Incomplete

Bug description:
if autologin is enabled in gdm, the encrypted private directory is not 
automatically mounted 

as ubiquitiy now has an autologin option, this will affect many users who later 
manually create an encrypted directory

from the security point of view, no auto mount for auto login this is certainly 
good and not a 'bug'; but it is unexpected and should be documented; also, both 
ecryptfs-utils and gdmsetup should explicitly warn for this case

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