ITunes and ISA Server 2004 Service Pack 2


Prior to SP2, if a requested destination name was in the list, it was accessed directly. With SP2 – a requested name in the list is accessed directly, unless IP addresses are included in the list. In that case, an attempt is made to resolve the site name to an IP address. Access is direct only if the resolved IP address is found in the list.


There have been lots of questions from customers on how to make ITunes work after applying ISA Server Service Pack 2.


First of all, some background on what’s happening. A server might return a compressed response (with an “Content-Encoding: gzip “HTTP header) even though ISA Server did not specifically request compressed data. For security reasons, if the ISA Server compression settings are not enabled to Request compressed HTTP content from servers, then ISA Server will deny the response.


This is what’s happening with ITunes.


The good news: the music can go on…You can configure ISA Server so that ITunes will work. Here’s how:




  1. On the General node, click Define HTTP Compression Preferences.


  2. On the Settings tab, add a computer set that includes the IP address of the site to the list.


  3. Select the site and click Set Compression.


  4. Enable Request compressed HTTP content from servers.


Let the music play!


Adina Hagege


ISA Server Product Team


Comments (16)

  1. jeremyvalentine says:

    What about ISA 2006? We cant get itunes store to work with Macs if I have NTLM and basic authentication enabled. Is this the same problem? When I disable NTLM the music store works fine. Can I create a rule that allows anonymous to the music store regardless of the authentication settings on the listener?

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  3. Russell Brown says:

    While I appreciate the help, I don’t under stand step 2 ‘add the site to the list’.  Can you be more specific?  Thanks Russell

  4. Nino Benvenuti says:

    Step 2 doesn’t make sense – when you click Add, you get the dialog to add a new  Network or Computer Set.  How do I add a site?

  5. Apologies for being unclear–I’ll update the entry, which should read "add a computer set that includes the IP address of the site to the list."

  6. Russell Brown says:

    If you start logging then access iTunes you get several IP addresses. Do you know what IP ranges are necessary?  Since you are bloging on setting up iTunes in ISA SP2 can you expand on step 2. Thanks

  7. Carl Perkins says:

    Exactly, is there a list of iTunes iP addresses. Surely everyone has to enter the same addresses and could list them here?

    Thank you

  8. PatRick says:

    Use the logging tab to find out. However these are the ones i use: 17.250.236.65, 69.44.123.19, 69.44.123.24, 69.44.123.26

  9. supreme says:

    sorry but i dont get this:

    On the General node, click Define HTTP Compression Preferences.

    where the hell is this option ? when i open up my isa2004 management i see ISA Server Administration with : Administration Delegation, Config. Firewall Chaining, Defile Firewall Client etc. and Additional Security Policy with "define radius server" etc.

    but WHERE should i find " define http compression preferences ?

    need help!

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  13. christophe says:

    More IP addresses: 194.109.192.22 and 194.109.192.7

  14. Shayne Turner says:

    I have added all the IP addresses as instructed.  I still can’t get iTunes store to work.  What am I missing?

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