Issues with WPAD not working for me.
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 IIRC, WPAD doesn't work with HTTPS so if you're using pfSense to serve them then you should be running WebGUI in HTTP mode. 
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 @KOM: IIRC, WPAD doesn't work with HTTPS so if you're using pfSense to serve them then you should be running WebGUI in HTTP mode. i understand that. My WEBGUI is on port 8800/HTTP. it still is not working after going through you guide exactly given from Ageekhere. Also just FYI. I notice the files all are able to be downloaded in the browser, when i use my external windows 2016 webserver that I run on my VM, but im not sure of the configuration after that for http and https blocking in pfsense. 
 i am wondering if its something going on somehwere else when trying to use pfsense as the webserver.
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 one thing I am noticing is that when i go to http://192.168.1.30/wpad.dat in my browser it downloads, but when i access http://wpad/wpad.dat it seems to not work. Could this be an issue with DNS resolver? 
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 why do you need the host as wpad? on most setups, the wpad url includes the ip address. 
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 I was following the steps in the guide created by ageekhere to be able to filter HTTPS traffic. https://forum.pfsense.org/index.php?topic=112335.0 One thing that is happening is when i enable the DNS host override it will not block any sites. 
 I wanted to do the WPAD so I would not have to do the MITM setup in the proxy. but at this point all I can get to work is the WPAD disabled with Transparent proxy enabled but of course its not blocking HTTPS traffic.
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 One thing that is happening is when i enable the DNS host override it will not block any sites. The DNS override on it's own does not block sites. but at this point all I can get to work is the WPAD disabled with Transparent proxy enabled Did you follow all the steps? it should work. 
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 I followed every step to the T! its crazy even when i try to browse to : http://192.168.1.1/wpad.dat or .da , or the proxy.pac file they are not downloading at all in chrome or IE. 
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 Do you have auto configure enabled in internet options? 
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 Have you tried setting dns suffix on windows client? 
  
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 I got it working now. I had to use the unofficial WPAD package marcelloc created using nginx and it actually started working as it should. Thanks fellows! 

