@P3R:
Rules in pfSense affect traffic coming IN on it's interfaces only. To log what I think you want, both the local source address and the destination (website or other) address in your logs, you should apply logging on the LAN interface rule allowing the traffic. The response to those requests will not, as far as I know be possible to log (and since the request is the interesting part, I see no reason).
Excellent. Thanks! You're right- I needed to enable logging in LAN rules.
@P3R:
I'm sorry I have no idea. I almost always use Chrome (later more specifically Iron browser) and can't recall ever having experienced what you report. I wouldn't expect that to be the cause for your issues but I don't use 2.2 yet, only 2.1.5.
After a bit of playing around I (mostly) figured out how to solve this problem.
First of all, I was having problems with the constant reminders because I had too many different machines/browsers connected to the webGUI at once (more than 3).
Second, I figured out how to get the browsers to trust the TLS certificate. I created a new CA certificate and added it to my Trusted Root CA store. Then I created a new server certificate off that root with pfsense. <domain.xxx>as the CN, being sure to also set that as a subject alt name. It took a couple reloads of the page after that (who knows why), but then my browsers now accept and trust the pfsense TLS certificate.</domain.xxx>