There's a problem with sshing with a user now. To use the chroot jail the user's dir and shell have to be changed in /etc/passwd. I was using the a user to play with chroot. Yesterday I played with it and was getting permission denied when trying to ssh in. When I was done trying to get chroot to work, I changed the user's dir and shell back to normal. Tried to ssh in to make sure it was normal again and it was. Tonight I played with it some more only changing the /etc/passwd file again. I got permission denied again when trying it with chroot jail running and changed /etc/passwd back to normal again. I tried to ssh in like normal again and permission is denied and I'm prompted to re-enter the password. I tried restarting ssh and triple checked the /etc/passwd user line. I can login to the machine while at it or through Webmin, but not ssh now.

The only other things I did were within the chroot environment with the user in /home/jail/home/user, in which I removed the user's dir in the chroot environment and readded the user to the jailed environment. That's it. Anyone have any ideas what permission is now denied just from changing /etc/passwd the second time?

//Old issues cleanup. Please disregard if solved/no longer applicable.

That's it. Anyone have any ideas what permission is now denied just from changing /etc/passwd the second time?
My guess would be you changed stuff you forgot about. Best chance would be to run sshd and ssh both with triple debug/verbosity switches and check the output.

Wrt OpenSSH chrooting, did you have a look at http://chrootssh.sourceforge.net?