I think I got things worked out now. Ended up with:

pihole using google for DNS (8.8.8.8, 8.8.4.4) and the pfSense box so local DHCP systems will resolve.

pfSense is set to use just the piHole for DNS.

I did see the piHole having an IPv6 address set even though I have no way to use it other than locally so I disabled that. IPv4 only now. Not quite sure if that could have been mucking things up or not.

The website I was having problems with now loads but after the page is displayed it's trying to load other content and so far I haven't quite figured out what. The website is a mess of CDN network content so this may take awhile to dig into.

On 02/19/2017 08:05 AM, Moshe Katz wrote:
Steve,

The easiest next step to troubleshoot is to manually set the iPad's DNS to point to the pfSense. If that works, then you know the problem is in the PiHole. If that doesn't work, try setting the iPad to use Google Public DNS (8.8.8.8 and 8.8.4.4). If that works, then the problem is the pfSense. If that doesn't work, then the problem is the iPad itself.

To change the iPad's DNS server, you can follow these instructions: http://www.macinstruct.com/node/452

The next troubleshooting step would be to do a packet capture of whichever leg of the query (iPad -> PiHole, PiHole -> pfSense, or pfSense -> Internet) seems to be the problem. Set a filter on the packet capture to capture only DNS traffic (port 53). Then you can see if the request is malformed, if no response ever comes back, or if the response is malformed.

Moshe

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Moshe Katz
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On Sat, Feb 18, 2017 at 3:35 PM, Steve Berg <[email protected] <mailto:[email protected]>> wrote:

    Having an odd issue with DNS not resolving for one hostname from
    one client.

    I've got this setup:

    cable modem -> pfSense (2.3.2-RELEASE-p1) -> internal network

    Inside the network I have a piHole running on an RPi3 and all
    systems get a statically mapped DHCP address (from pfSense) and
    the piHole is set to be DNS.  piHole uses pfSense as it's upstream
    DNS so all all internal hostnames resolve locally from
    piHole/pfSense, outside hostnames come from dnsmasq on piHole or
    pfSense.

    On my iPad when connected to the WiFi I cannot resolve the IP for
    our local newpaper's website, all other hostnames seem to resolve
    just fine.  That newpaper site resolves for other clients on the
    internal network with no problem including an iPhone on the WiFi.
    As soon as I turn the iPad's WiFi off and connect via Verizon LTE
    it sees the newspaper site just fine.

    Only the one wireless device is showing this problem so far.
    Nothing on the wired network, and not the other three wireless
    devices.

    I've turned on DNS forwarder on pfSense and DNS resolver, but I
    really don't think it's either of those because I'm not seeing the
    problem on anything but the one iPad.

    I'm fairly new to pfSense but not to general networking so this
    one has me stumped at the moment. I have looked into using
    pfBlockerNG instead of pihole but I'd rather figure this problem
    out first.  If anyone has suggestions on what might be wrong and
    how to fix I'd appreciate it.


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