You can upgrade a pfSense via SSH live so the client does not have any down time. These commands will also solve the issue of “Unable to check for updates” that can occur in corrupted 2.3.3 versions.

  1. Enable SSH on pfsense from System > Advanced and check enable secure shell.
  2. Connect to the pfSense with Putty via SSH and login with pfSense credentials
  3. Once logged in, you may need to select one of the numbered options to get to the system shell, (depending on the firmware version SSH may just dump you right into shell I have seen both)
  4. The commands to update are as follows:
    1. pkg-static update -f
    2. pkg-static upgrade -f
  5. Let this complete, and you pfsense will now be on the latest firmware, without having to reboot!