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.


--
//-        Fixer of that which is broke        -//
//-        Home = [email protected]        -//
//- Sinners can repent, but stupid is forever. -//


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