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Voici un série d'articles sur le sujet qui explique comment mettre en place cette fonctionnalité ainsi que les pièges à éviter
A Description of the Automatic Discovery Feature
https://support.microsoft.com/kb/296591/EN-US/
Automatic Discovery for Firewall and Web Proxy Clients
https://www.microsoft.com/technet/prodtechnol/isa/2004/plan/automaticdiscovery.mspx
How to configure firewall and Web proxy client Autodiscovery in Windows Server 2003
https://support.microsoft.com/default.aspx?scid=kb;EN-US;816320
How To Configure Firewall and Web Proxy Client Autodiscovery in Windows 2000
https://support.microsoft.com/default.aspx?scid=kb;en-us;309814&sd=tech
"Automatically Detect Settings" Does Not Work if You Configure DHCP Option 252
https://support.microsoft.com/default.aspx?scid=kb;%5bLN%5d;307502
You cannot use an IP address for AutoDiscovery in ISA Server 2004 Web Proxy Client
https://support.microsoft.com/?kbid=891066
The DHCP clients may not obtain the configuration script when you use DHCP Option 252 to automatically configure Internet Explorer
https://support.microsoft.com/kb/911072/en-us