Problems with Google/GMail
I just set up a new install of pfsense 2.4.4_2 and I'm having an intermittent issue with accessing google.com and mail.google.com. Sometimes it loads just fine and sometimes I get an error page saying to try enabling different TLS versions. TLS is already enabled. (this is the same error page I usually get when a page is blocked)
I think this could be an issue with squid/squidguard, since that's the only thing I really have set up on it at the moment. but I just don't know what it could be. I have it set up in transparent for http and https. And it seems to be working fine for everything but google. I've tried adding all the google related domains I see in lightsquid reports to the whitelis to rule out that they are getting blocked, but it doesn't seem to change anything.
I followed this guide to set this up, but skipped over all the parts about setting up the safe search host overides because that isn't something I need to do.
Before I had actually put this in place where about 20 people are using it, I set it up in a small test and it worked just fine, and I still have the test setup running and have made sure all the settings are the same, and the test is working just fine.
Commonly that's caused by Squid and clients resolving URLs to different IPs because they are using different DNS servers.