Jeff M Belt
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Login to Web UI and select System / Package Manager / Available Packages , find and install package squid.
Wait until squid package is installed.
After successful installation goto Services / Squid Proxy Server, select Local Cache tab, scroll all the way down and click Save.
Now select General tab, set the Enable Squid checkbox, select both LAN and loopback interfaces for Squid to bind to, scroll all the way down and click Save.
Fixing the Squid Installation
Click System -> Advanced
Click on Enable Secure Shell
Log into the pfSense box and open a command shell (option 8 on the menu)
Change directories to /usr/local/etc/squid
Edit the serverkey.pem file and locate the line which reads
-----END PRIVATE KEY----------BEGIN CERTIFICATE-----
Split this line into two, so it reads
-----END PRIVATE KEY-----
NOTE: the number of dashes are critical, so count them correctly, meaning there are five before and after the Key and Certificate markers.
Save the file and reboot your pfSense box.
After reboot, login to Web UI, select Status / Services. The red checkbox on the right will indicate Squid service is NOT up and running.
Now adjust your browser configuration to point to pfSense box and try browsing the web. Squid is now working.
That’s it! Squid should be up and running. The status of the squid proxy can be checked by clicking Status > Services.