Automatic Proxy Detection: Curious Issue

I have an issue with the Automatic Proxy Detection in Snow Leopard in that its not consistently detecting the correct settings.
One one of my networks that I manage, Win2k3 with DHCP 252 set to http://wpad/wpad.dat and a DNS CName for WPAD to the server hosting the file I am unable to use automatic detection.
Another network with 10.5 servers, and only an Alias/CName to the server hosting the wpad.dat will work.
Another with a Win2k8 as the main server with just a CName to the server likewise works
I will be testing another Win2k3 server later on to see how it works.
However, entering the path to http://wpad/wpad.dat in the configuration option works successfully until I go home and there is no wpad configuration.
Other machines on the network can successfully use Auto Proxy Detection (Windows & Mac's with Firefox as the browser)
However, on other networks this is setup the same way and it does work.
Has anyone experienced issues with WPAD and Automatic Proxy Detection in SL when moving between networks?

Resolved.
Removed the DHCP 252 Option forcing the computer to rely solely on DNS for detecting the wpad.dat (and the wpad cname)
If the DHCP & DNS Methods are used it will fail.
If the DNS Method is used, it will succeed

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Hi,
Sorry for the late response.
Since the issue is complex and difficulty to troublshooting, we discussed for some time corssing the specialty. Here is some direction we may let you know to do further troubleshooting:
capture network trace to confirm whats happening across the wire.
confirm the wpad.dat is the expected.
If you have any difficulty when doing this, we suggest you to contact with IT Pro Support via the link below:
http://technet.microsoft.com/en-us/ms772425?WT.mc_id=SMCfoot_ENUS_TEXT
I think it can help you define the root cause via some deeper tools due to the complicated symptom you have.
I appreciate your understanding and time.
Best Regards,
Annie Gu

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