I updated this webserver from 9.0 to 9.2 running these commands as root (or run every command via sudo):
$ make -C /usr/ports/ports-mgmt/portupgrade install clean $ freebsd-update -r 9.2-RELEASE upgrade (It'll tell you which base packages will be upgraded) $ freebsd-update install (You'll be asked to merge some config files) $ shutdown -r now $ freebsd-update install $ portupgrade -f ruby $ portupgrade -f 'ruby*-bdb*' $ rm /var/db/pkg/pkgdb.db /usr/ports/INDEX-*.db $ pwd_mkdb -p /etc/master.passwd $ portupgrade -af (You'll have some coffee now, but don't go away as some ports may show a dialog with some options to choose from) $ freebsd-update install
Finally, either reboot the machine or (re-)start enabled services in /usr/local/etc/rc.d/ manually.
Update 2016-05-08: Recently, I have been using a simpler and safer way to update FreeBSD boxes:
$ make -C /usr/port/ports-mgmt/portmaster install clean $ portsnap fetch update (Make sure you use a shell from the base operating system) $ chsh -s /bin/csh root (Make sure /etc/nsswitch.conf refers to shared libraries from the base os only, e.g. do not use libnss_winbind.so from the ports during the update) $ vi /etc/nsswitch.conf $ freebsd-update -r 10.3-RELEASE upgrade (It'll tell you which base packages will be upgraded, and you'll be asked to merge some config files) $ freebsd-update install $ shutdown -r now $ freebsd-update install $ portmaster -af (You'll have some coffee now, but don't go away as some ports may show a dialog with some options to choose from) $ freebsd-update install (Optionally, you may want to free some diskspace) $ rm -rv /boot/*.old /usr/ports/distfiles/*