I just had PFSense installed for my new firewall, and I think I’ve figured most of my issues, out, but I haven’t been able to find anything on my last couple of items. (One of the forums was moderated by @Cry Havok - same person, right?)
Outlook no longer connects to the server, but I can connect using OWA.
Windows update no longer connects
Items in my blacklist doesn’t get blocked regularly
Aye, that’s also me. Though, I’ve not been there in some time as I stopped using pfSense when I had to change ISP, and my new ISP would only provide all in one modem/router pieces of rubbish.
Out of the box, a base pfSense install shouldn’t break any normal activity. That it has means something’s gone wrong, or the defaults have changed, and I’m too long out of touch to help I’m afraid.
PFSense shouldn’t be doing any outbound filtering out of the box—it should come out as blocking all inbound and allowing all outbound. So the first thing to check would be to see if you’ve got any outbound filtering accidentally enabled.
A personal recommendation: if you’re not too attached yet to PFSense, I’d highly recommend Smoothwall (the free community edition) instead. I used it for years and years, and I prefer it over PFSense due to a number of streamlined configuration choices (unified interface for packet filtering, port forwarding and DNAT/SNAT rules, rather than having to make a NAT rule and then separately make a matching packet filter rule, for example). It’s IMO much, much more newbie-friendly.
(However, it’s based on the Linux kernel instead of BSD, and that tends to make BSD people hyperventilate. YMMV. If you don’t have Important Feelings about the One True Kernel, then whether you’re using Linux or BSD won’t matter )
I use Smoothwall at home, but the network admin at the school prefers PFSense, so that’s what I have. I did some more troubleshooting, and I don’t think it’s a PFSense issue for the Outlook and Windows update stuff. This is happening on one computer, not the whole network.
The inconsistent filtering of my blacklist is frustrating, though.