hmm..allright lets start from the basic…
could you first try just one LAN segment to see if its working first?
Why dont you let WPAD run on pfSense? Did you add the 252 on the DHCP on windows server?
can you do nslookup WPAD? this is my WPAD
Also want to side note something about the VPN with OpenVPN theres issues see this...
https://forums.openvpn.net/topic21290.html
function FindProxyForURL(url, host)
{
if (isPlainHostName(host) ||
shExpMatch(host, "*.local") ||
isInNet(dnsResolve(host), "192.168.3.0", "255.255.255.0"))
return "DIRECT";
return "PROXY 192.168.3.254:3128";
}
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