WPAD/Squid fail, having trouble figuring out what went wrong

  • I've got PFsense set up with Squid running. I had it running okay in transparent mode, but after reading that WPAD is a better alternative, I decided to make the switch.

    I pretty much followed "WPAD Autoconfigure for Squid" tutorial exactly. I added the appropriate entry to my DNS server (Windows Server 2012 if it matters), restarted my browser (Chrome), and tried to browse a site, but I was getting a "Proxy Misconfiguration" error, no sites at all would load, even my PFsense webconfigurator. So after panicking a bit, I reverted to a previous config, deleted the DNS entry and cleared my DNS cache. But I don't know what went wrong, so I'm hoping to get some help here.

    Traffic was getting directed from the Proxy to PFsense, as I have evidence in the log:

    Squid - Access Logs
    Date	IP	Status	Address	User	Destination
    20.05.2016 16:00:01	TCP_MISS/000	http://crl.microsoft.com/pki/crl/products/MicrosoftTimeStampPCA.crl	-
    20.05.2016 15:59:55	TAG_NONE/503	kv401-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:55	TAG_NONE/503	geo-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:55	TCP_MISS_ABORTED/000	http://ssw.live.com/UploadData.aspx	-
    20.05.2016 15:59:52	TAG_NONE/503	geo-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:52	TAG_NONE/503	geover-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:49	TAG_NONE/503	disc401-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:49	TAG_NONE/503	geover-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:49	TAG_NONE/503	kv401-prod.do.dsp.mp.microsoft.com:443	-	-
    20.05.2016 15:59:47	TAG_NONE/503	disc401-prod.do.dsp.mp.microsoft.com:443	-	-

    Here's my wpad.dat (.100 is pfsense, the gateway)

    function FindProxyForURL(url,host)
    return "PROXY";

    Squid is vesion 3.5.19
    PFsense version 2.3-RELEASE

    What's confusing to me is why I couldn't even load the web configurator. Since I entered the IP directly (, why was it being sent to the DNS server at all, and therefore being redirected to the Proxy? I'm sure this is just something in the config that I missed, but given the process to start it up, I can't really go ticking boxes and breaking the internet over and over.

  • for the wpad you need to go direct for local
    follow this https://forum.pfsense.org/index.php?topic=112335.0

  • That was it! Thank you.

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