For regular user accounts, a properly configured chroot jail is a rock solid security system. I've already written about chrooting sftp session using rssh. According to OpenBSD journal OpenSSH devs Damien Miller and Markus Friedl have recently added a chroot security feature to openssh itself:
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Unfortunately, setting up a chroot(2) environment is complicated, fragile and annoying to maintain. The most frequent reason our users have given when asking for chroot support in sshd is so they can set up file servers that limit semi-trusted users to be able to access certain files only. Because of this, we have made this particular case very easy to configure.
This commit adds a chroot(2) facility to sshd, controlled by a new sshd_config(5) option "ChrootDirectory". This can be used to "jail" users into a limited view of the filesystem, such as their home directory, rather than letting them see the full filesystem.