pfSense

In 2.2 and using DNS Resolver it seems other way around. If you don't config custom DNS on DHCP client don't pic DNS servers.
This was tested weeks ago. I should try the last one DNS Resolver.

I tried it on 2.2 and 2.1.5 and both worked as expected, my test config is similar to the one you posted.

Oh dear - I was thinking this was going to be a nice clear bug, since I noticed it on my test 2.2 system, then did similar on a production 2.1.5 system and got the same problem - dhcpd.conf looks good, but "ipconfig /all" on the client shows it did not get handed the custom DNS servers.
I will try harder tomorrow with a few different clients and see if I can characterize it better...

Domain-Name-Server is specifically set in pfSense DHCP config to 10.49.48.*250* and that is delivered correctly to the client (events at 16:15:52 in the packet capture).

Detail in post 6 should NOT be 10.49.48.1, it should be 10.49.48.250 - as per the packet capture. (There seems to be no way to update a dodgy comment on a bug)

Phil - do you not see a pencil to the right of your comment? That's how you can edit previous posts. I thought it was set so anyone can edit their own posts.

On the issue at hand, that's an ISC dhcpd issue from the sounds of it. We're configuring it correctly, it works correctly in general, for some reason in that circumstance w/wpad it doesn't do what it's configured to do. It seems maybe this is referring to the same (or similar) issue?
https://lists.isc.org/pipermail/dhcp-users/2013-May/016707.html

Had a look at dhcp.c ISC source code and submitted a bug report. Then after more research I found this:

Extend the DHCPINFORM processing to honor the subnet selection option
and take host declarations into account.
Thanks to Christof Chen for testing and submitting the patch.
[ISC-Bugs #35015]

This was committed to master of ISC-DHCP on 2013-12-14 and is in V4.3.n
The code diffs look like a really good thing to actually even bother looking up the host-specific options when responding to an INFORM from the client. The previous code did not even try, so it was not a little bug, more a missing feature.

The 35015 code does not appear in the V4.2.n branch. FreeBSD 10.1 pfSense 2.2 has V4.2.6 (and V4.2.7 is current-stable on ISC web site), so neither of those will have this fix/enhancement.

I expect this will be fixed when FreeBSD and pfSense is using V4.3.n of ISC-DHCP - maybe the 4.3.n series is not yet production-stable???

Anyway, this can be closed here, as the issue is dealt with upstream and the fix should flow into FreeBSD and pfSense over time.

Received this text in email today from dhcp-bugs@isc.org :
--------
Yes 4.3 added this functionality. There was a bug
in the earlier versions of it that we fixed in 4.3.2.

Marking this as resolved. If you try 4.3.2 or later
and find a problem you can either re-open this
ticket or open a new ticket.

regards,
--------
When FreeBSD and then pfSense end up with ISC DHCP 4.3.2 or later then this should work.