@jimp
Thank you very much for your reply! This solved my problem.

I suppose I could have worded my previous comment a little differently. I've found lots of others online who are having a similar troubles. As such, I wasn't so much surprised that nobody else was having the same issue, rather, I was surprised that I hadn't yet found an answer similar to what you've provided, above.

Thanks again for your help with this!

How to configure

You should now see squid pkg version 0.4.44_7 which includes the recompiled clamav package.

Nope, I have never seen that error message before but it seems to be related to the backend.
Can you post a picture of how your backend is configured

@jimp could you point me in the right direction how to setup so HAProxy on pfSense handels the certs ( not just getting them )

@piba

How do I get information about this image?

Is Squid the only package on the pfSense box?

Also I would check if the firewall rule that Squid adds in transparent mode is conflicting
with other firewall rule's.

With that amount of user's there is quite a lot of tuning that can be done.

Common is literally applied for everyone. Group policies are only for those clients inside the group. The order is important. Did you confirm that your clients are even using the proxy?

That was it, thank you for your help!

Problem solved.
Set SSL/MITM Mode to Splice All.

Ok after some reading, it seems I don't need to filter https. All I really need to do is block certain https domains from my kids on my home network while allowing all other traffic, prevent kids from circumventing proxy, monitor traffic stats per IP, and no issues with online games like logging into Warframe.

To block https domains, I found some info on setting the ssl intercept to "splice all" and putting ".*" in the acl whitelist, then use squidguard to block https. However, I'm not exactly sure how to set this up with squidguard or if it will fix my Warframe login issue.

I'm trying to learn this so I don't really want to use something like OpenDNS if I can help it. I'm running psSense in a VM with working backup so I'll try any suggestions because I can easily restore my pfSense firewall.

Thanks.

@mats So part of the problem was my rules but the final stick ended up being a bug in the upgrade to the most current release where my default gateway was no longer 'marked' default.... what a headache.

I did finally manage to get Zimbra OSE running in a docker alongside a NextCloud docker to work for files as well. Only then did I fully realize that since I chose the Open Source edition, I cannot fully integrate it into my android for calendars and such which is a major letdown. I was so impressed with the webmail features that I over looked the limitations of the free version.

I may look into iRedMail. I didn't like the webmail portions but in the end I doubt I will really be using it compared to the ability to have fully integrated calendar & contacts.

Ended up canceling Squid for HAProxy.

using the HAproxy Devel did the trick

@landrocket
The best way I have found to set up squid on a home network is without transparent.
It is pretty simple to set the proxy setting's in the browser.

Also has the added benefit if you have a problem connecting you can reset your browser
and just bypass the proxy until you figure out the problem (check the real time log's)

The way I set up mine is pretty much default. (Create Internal Cert. of Auth.)
1)Enable Proxy
2)Select Lan and Loopback
3)Allow User's
4)Resolve IPv4 first
5)Disable ICMP Pinger helper
6)Enable SSL filtering
7)Splice Whitelist Bump otherwise
8)Select Lan
9)Proxy port-3129
10)Compatibility mode-intermediate
11)Cert. Adapt Not Before
12)X-Forward (transparent)
13)Disable Via Header
14)URL Whitespace (Strip)
15)X-Forward (transparent)

After you reboot the firewall you can go to the ACL's tab and can enter in site's that you don't
want to SSL bump- here is what I use. Window's Updates, Live Mail, OneDrive, Steam etc.
Some of them might not be relevant anymore. But steam will take the proxy down quick if
it isn't whitelisted.
I am sure there is a way around that but I didn't want to put in the effort.

0_1540791260483_Whitelist.txt