As example, in Forefront TMG I can have a wpad entry in the DNS and computers discover it and autoconfigure the web proxy. When the user tries to go to the Internet he is promptped for the crendentials.
In iPhone or iPad it doesn't work. Which is your recommeded way of implementing an authenticated proxy that works for mobile devices?
This apparently is an issue with iOS. It does not automatically pick up WPAD.
You can work around this by going into the Wi-Fi settings for your network, setting the HTTP Proxy setting to Auto and entering
http://wpad/wpad.dat?
into the URL setting for the device.It depend on requirements. May be You can use authentication on web portal (known as Hotspot)?
Trying to implement funky wireless authentication schemes such as EAP etc is not a very viable solution except in a small number of edge cases - and they don't authenticate users - they authenticate devices. If you want to authenticate users then use a captive portal with transparent redirection at the DHCP gateway address.
setting up the authentication part is simple with Squid is simple, although unless you upgrade to a non-Microsoft OS to run it on, you won't be able to do the transparent proxying necessary to make it seamless.