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:
- Stop the Squid service
- Attempt to upgrade the Squid package
- Wait until the process stalls
- Use Putty to SSH into the pfSense firewall
- Select the SSH option
- 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.