same issue for me on jaunty 2.6.28.11 using libpam-ssh 1.91.0-9.3 and
ecryptfs-utils/libecryptfs 73-0ubuntu6.

i dont have the whole homedir encrypted, only the ~/Private folder, 
nevertheless i get a "gdm[3587]: Mount of private directory return code [256]" 
or a "keyctl_search required key not available" when logging on via gdm/console 
after entering my ssh passphrase.
i sourced the pam-ssh-auth and pam-ssh-session files in login, gdm and 
gdm-autologin as instructed in pam_ssh manual. the pam_ecryptfs module is 
loaded with common-auth and common-session, both as optional. 

while disabling pam_ssh and using pam_ecryptfs works as intended...

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Auto mount of encrypted home directory RANDOMLY stops to work
https://bugs.launchpad.net/bugs/364015
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