Just to clarity, is this what you describe . . . As part of your investigation, I would suggest you divide the problem into manageable chunks to confirm [and exclude] where the issue may or may...
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Just to clarity, is this what you describe . . . As part of your investigation, I would suggest you divide the problem into manageable chunks to confirm [and exclude] where the issue may or may not reside. For example, is it a VMware Workstation or pfSence related problem, do the various individual subsystems operate correctly (VMs, Virtual Networks, WAN, pfSense/DHCP, etc.,). So would suggest first of all, checking that the Host Only VMs are working as expected. So start with giving the connected Win 10 VM devices for the time being, fixed IPs within the same subnet (or alternatively, or in addition to, temporality enable the VMware DHCP on the Virtual Host Only Networks), and then confirm that they can communicate with each other and the pfSense VM. Then do the same for the FreeBSD VM. Then, if this all works out, return the VM's back to DHCP to focus on the pfSense DHCP services. For this I would suggest reviewing the relevant pfSense documentation to provide a bit more focus on where the issue may reside. I'm assuming that the pfSense VM is successfully picking up a DHCP allocated IP from your WAN [Bridged] network ?