I am making progress slowly but surely. Anyway as an FYI, the path to use when using the chroot command is relative to the chrooted environment. In my case I must use:

chroot /jail up2date -uik /tmp ... not chroot /jail up2date -uik /jail/tmp

I am now struggling with getting the up2date working in the chrooted environment. I am able to enter up2date as a command and bash doesn't scream with the "command not found" message, but nothing happens. I have copied over these files into the chrooted environment:

/usr/lib/libglib-2.0.so.0
/lib/tls/libc.so.6
/lib/ld-linux.so.2
/usr/bin/up2date
/usr/bin/up2date-config
/usr/bin/up2date-nox
/usr/sbin/up2date
/usr/sbin/up2date-config
/usr/sbin/up2date-nox
/etc/sysconfig/rhn/sources
/etc/sysconfig/rhn/systemid
/etc/sysconfig/rhn/up2date
/etc/sysconfig/rhn/up2date-keyring.gpg
/etc/sysconfig/rhn/up2date.rpmnew
/etc/sysconfig/rhn/up2date-uuid
/etc/sysconfig/rhn/rhnsd
/usr/share/rhn/RHNS-CA-CERT
/usr/share/rhn/RPM-GPG-KEY

Using ldd pointed out all of the library files that I needed. I am not sure if any additional files are needed.

Any help is much appreciated.