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[Jim <jdblaich@xxxxxxxxx>]

I have the same problem.

My install was an 8.04 and I did an upgrade to 8.10.  I had it set up
under 8.04 to automatically log me in.

I had some success but it isn't persistent.  Also the following command:

ecryptfs_insert_wrapped_passphrase_into_keyring ~/.ecryptfs/wrapped-
passphrase LOGIN_PASSPHRASE

doesn't work for me.  I have to replace the underscores in the command
to be hypens, so the following command works:

ecryptfs-insert-wrapped-passphrase-into-keyring ~/.ecryptfs/wrapped-
passphrase LOGIN_PASSPHRASE

I had to install keyutils

I set my system to not automatically login.  This didn't make a
difference. I have to issue the command:

ecryptfs-insert-wrapped-passphrase-into-keyring ~/.ecryptfs/wrapped-
passphrase LOGIN_PASSPHRASE

after each log in, regardless of whether I'm set up to automatically log
in or not.

then I can mount the private encrypted directory with the following
command:

mount.ecryptfs_private

Now, really I do find it a big contradiction to allow someone to sit
down at my workstation while I'm not there and get into the private
directory.  What's the purpose if not to ensure that certain files are
not accessible to anyone but me.  It would seem the way to really make
this work is to allow me to double click on it say in nautilus and be
prompted for my pass key, or to mount it and be prompted (the same way
sudo does).

I can't afford the focus nor the time to log out each time I walk away
from the computer and if you say that lock the screen after x amount of
time, that sort of minimizes (and somewhat negates) the need to encrypt
things.

Issuing the two commands at the prompt sort of secures things for me but
it is very inconvenient and the fact that the command is quite lengthy.
I also issue a lot of commands at the terminal prompt so I'd have to
scroll back a lot over time.  I'd find myself using it less and less
till it falls to obscurity, thus making this "alleged" innovative and
compelling feature pointless.

-- 
Cannot open Private directory after a reboot when "Automatic Login" enabled
https://bugs.launchpad.net/bugs/259631
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which is subscribed to ecryptfs-utils in ubuntu.

Status in eCryptfs - Enterprise Cryptographic Filesystem: Fix Released
Status in “ecryptfs-utils” source package in Ubuntu: Fix Released
Status in ecryptfs-utils in Ubuntu Intrepid: Fix Committed

Bug description:
Binary package hint: ecryptfs-utils

I created an encrypted private directory following the instructions here:

https://wiki.ubuntu.com/EncryptedPrivateDirectory

Everything worked as it should until I rebooted. When I try to mount my private directory I get the following message:

 jimk@intrepid:~$ mount.ecryptfs_private
keyctl_search: Required key not available

When I go to create a key, I get the following message:

jimk@intrepid:~$ ecryptfs-setup-private
ERROR: wrapped-passphrase file already exists, use --force to overwrite.

I can create a new passphrase if I use the force option, but I shouldn't have to do this everytime I reboot