There is a defect with pfSense 2.4.5 and the Package Manager. When installing, upgrading, or removing packages, the process will not complete. For the Squid package, I did the following to upgrade:

  1. Stop the Squid service
  2. Attempt to upgrade the Squid package
  3. Wait until the process stalls
  4. Use Putty to SSH into the pfSense firewall
  5. Select the SSH option
  6. Execute the command to kill the Package Manager and then Exit
killall -9 pkg-static

Reference the following forum post on the Netgate pfSense forum for more info.