@amrogers3:
Hi Wallabybob, thanks for the reply. Looks like I finally found the issue. The problem lies with a virtual interface utilized by VMware Fusion.
Seems like a lot of people misconfigure their pfSense systems by configuring multiple interfaces with the same subnet.
@amrogers3:
I do have a question regarding EM0. I only have two interfaces EM1 which is WAN, and EM0 which is LAN. I have VLANs set up on EM0. I understand this may present a problem but can you go into more detail as to potential problems with VLANs on EM0? I know you said EM0 may "capture" packets without a VLAN tag but all traffic should have a VLAN tag.
I am researching an additional NIC so I can move the VLANs from EM0.
If all traffic on an interface has VLAN tags then there is no need to use the parent interface (in your case em0) as a pfSense interface. A concern I have in my own configuration is that if I have my LAN interface as a VLAN and my VLAN capable switch fails I'm not sure how I would reconfigure my pfSense. Consequently (and because there is plenty of spare bandwidth capacity on the interface) I have WAN and a DMZ as VLANs on the same physical interface. If I need to reconfigure because my VLAN switch has died I can still access my pfSense over the LAN interface.
I suspect you would have plenty of spare capacity on the interface you are currently using as the WAN interface to support WAN and a number of your VLANs.
I think one of the challenges on having tagged and untagged traffic on the same interface (or switch port) is that there is a potential ambiguity with equipment that doesn't support VLANs. Will such equipment ignore VLAN tags or discard traffic with VLAN tags?