I've tried asking on the IPLeak forums about what the 100 errors mean and no one has come back to me with an informative reply. Best i can figure out the errors signify that no DNS servers were found or able to be verified as leaking or not.
While i can't rule out the possibility that its more an issue with IPLeak or something else, to me it seems very conclusive that the problem lies with the update to PFsense and its dns resolver feature.
I've checked, double checked and triple checked that the settings I'm using in 4.4 are the same as what i use in 4.3. I've had 2 boxes running side by side, one using 4.3 and the other using 4.4.
In 4.4 it fails to work and i get the 100 errors. In 4.3 it works fine and i get 1 result with no leaking detected and more importantly no errors. It's not the browser or computer i use to access the site that's the problem as they stay they same. The only thing that changes is what version of PFSense I use.
I've even tried setting up PFSense to act as a router to my main internet connection so as to eliminate openvpn being an issue along with the other settings i use to make the openvpn connection work how i need it to.
Putting my ISP's router into modem mode and configuring PFSense in a very basic setup to get the IP from the modem and then accessing IPLeak through this box the problem still occurs. Where as if i access IPLeak through my ISP's router without the PFSense box i get no errors and it all works fine.
I understand what's been said about if it's wise to use a VPN providers testing site but it's what i've used without a problem in the past and can still use perfectly fine in every other scenario besides if PFSense 2.4.4 is used.
This make me believe that the common fault is PFSense regardless of the sites motives and trustfulness.
The only thing i can think of where it's not PFSense that's the problem is that in the update to the dns resolver feature its 'improved' things to the point its now incompatible with an old way of doing the dns checking or something that IPLeak uses.
If this is the cases then that's great. I can accept that. My only issue with this being the case then stems from the question: How do i know for sure and how do i figure out where the fault actually lies?