Cannot contact subnets from PFsense OpenVPN

[curttc]

I know there are a metric boat load of posts regarding this exact issue, but I have been struggling with it over the last couple of days getting it working in my home lab. Here's how I have things set up (I am fairly new to networking and firewalls, fair warning. Open to any suggestions.):

WAN ---> PFSense ---> USG

PFSense LAN: 192.168.5.1
USG LAN: 192.168.1.1

I have four different subnets assigned in my USG:

192.168.1.0/24
192.168.10.0/24
192.168.20.0/24
192.168.30.0/24

My traffic is routing fine through PFsense on any one of the subnets. Traceroute confirms it. I went ahead and configured OpenVPN correctly and can make the connection via the Windows client over WAN. I set my OpenVPN tunnel network to 192.168.100.0/24. The windows machine I am connected on has a 192.168.100.2, but it can only ping the tunnel network gateway (192.168.100.1). It cannot reach any other subnets, and also cannot reach the PFSense box at 192.168.5.1.

I've played around with firewall rules beyond the default ones set by OpenVPN and have also tried some of the push route customization options but still have not been able to get OpenVPN to route. Any idea what I'm doing wrong? Just trying to understand this better as a novice. Sorry if I left any important info out.

[Rico]

No idea about your USG stuff, but you should be able to hit pfSense at 192.168.5.1 with no problem.
Show your OpenVPN Config and Firewall Rules.

-Rico