Using ISA Server with Macintosh clients

 

Shijaz Abdulla, MVP

www.shijaz.com/isaserver

 

 

This article gives helpful hints on how to successfully configure Macintosh clients to access Internet through ISA Server through user authentication.

 

Background

 

Many organizations such mainly media and advertising agencies have a mixed environment containing Windows and Macintosh machines. It is recommended that you read the article Interoperability with Macintosh. This article explains some of common tasks required when operating Macintosh clients in a Windows Server environment.

 

Configuration required on ISA Server

 

Step 1.              ISA Server configuration

 

Mac OS prior to 10.x do not support SMB authentication and will require Basic Authentication (plaintext). Basic Authentication is not enabled by default on ISA Server 2004.

 

  1. Open ISA Management Console

 

  1. In the left pane, click Networks. In the bottom right pane, right click Internal and choose Properties.

 

  1. Click on the Web Proxy tab. Put a check mark next to Basic Authentication.

 

  1. Click  OK and click Apply to apply your changes.

 

 

Step 2.              Mac configuration

 

  1. If Internet Explorer is installed, open it.

 

    1. Choose Edit à Preferences.

 

    1. On the left pane, under Network, choose Proxies.

 

    1. Put a check mark next to Web Proxy and enter the IP address of your ISA Server

 

    1. Click Use Web Proxy for all.

 

    1. Click Settings next to web proxy. Set the Port to 8080. Method should be Normal. Enter the domain username and password in the space provided.

 

    1. Close the Web Proxy Settings window

 

    1. Try to browse to a web site. If prompted for password, enter it and click Save Password.

 

    1. Ensure that Internet access is available.

 

  1. If you are running Mac OS 10.x or using Safari browser

 

    1. Choose Edit à Preferences.

 

    1. Click on Advanced.

 

    1. Click the button for Setup proxies.

 

    1. Put a check mark next to Web Proxy and enter the IP address of your ISA Server

 

    1. Click Settings next to web proxy. Set the Port to 8080. Enter the domain username and password in the space provided.

 

    1. You can add the credentials to your keychain so that you don’t need to enter them over and over.

 

Observation:

 

If you are running Outlook 2001 for Mac or Entourage 2004 with Exchange Server, be sure to include mailserver.domain.com (FQDN of your Exchange Server) in the list of addresses that will bypass the proxy server. Otherwise Entourage/Outlook will not be able to access the Exchange Server and will continually prompt you for credentials to access the ISA Server.

 

 

Related Information

 

See article: Interoperability with Macintosh

See article: How to configure Macintosh clients on Exchange 2003 using Entourage 2004

 

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Disclaimer

 

The steps mentioned in this are results of testing in a lab environment. The procedure might require additional testing before being deployed on a live environment. I assume no responsibility for damage(s) occurring due to following this procedure or any other procedure listed on this site. Use it at your own risk!