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How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

This is an update to the article How to publish Small Business Server 2008 using a Windows Server 2003 Computer with ISA 2006 Standard Edition - part 2. The steps to correctly publish Outlook 2007 Autodiscovery were left out of the first article, and this was brought to our attention by Blair George, so thanks for that Blair! Below are the additional steps required to publish Autodiscovery.

Table of contents

You have two choices for publishing auto discovery, you can use a public DNS A(host) record named 'autodiscover.domain.com' which points to the same WAN address as 'remote.domain.com' or you can use a DNS SRV record. The A(host) record is on the face of it, a simpler method. Your DNS admin need only create a simple DNS entry, and your off and running. The SRV record I think may be a stumbling block for many a SBS admin – with the issues some ISP's and DNS hosting companies seem to have with a simple SPF key – who knows the results we will see when we ask for SRV entries!

Following the advice in Eriq Neale's 'SBS 2008 Unleashed' you can read that if you register your domain name using the built in SBS wizards, using one of the approved registrars, SBS will create all the required DNS records for you.

Obviously this won't suit all of us as we will already have a public domain name. So, you have to make your decision, because you can't use both methods. This Microsoft article will explain more: http://support.microsoft.com/kb/940881. For those of you who don't want to read the MS article here is a brief description of the AutoDiscover process and possible problems you may encounter. When you run the Outlook account wizard, you are presented with the page; 'Auto Account Setup' and you must fill in your name, email address, and password. Clicking on Next will start the auto discovery process.

Outlook now tries to connect to some predefined URLs:

  • /Autodiscover/Autodiscover.xml">/Autodiscover/Autodiscover.xml">https:///Autodiscover/Autodiscover.xml
  • /Autodiscover/Autodiscover.xml">/Autodiscover/Autodiscover.xml">https://autodiscover./Autodiscover/Autodiscover.xml
  • /Autodiscover/Autodiscover.xml">/Autodiscover/Autodiscover.xml">http://autodiscover./Autodiscover/Autodiscover.xml

If one of these URLS is valid, Outlook will continue on the AutoDiscovery process. If you are running AutoDiscover over SSL your outlook client will now be prompted to accept a certificate warning, before continuing. This is because we are connecting to 'autodiscover.domain.com' instead of 'remote.domain.com' which is the domain our SSL Certificate is valid for.

If we use A DNS SRV record, which is new for Outlook 2007 (http://support.microsoft.com/kb/939184/ Description of the update rollup for Outlook 2007: June 27, 2007) we avoid this certificate warning altogether. The SRV record tells our Outlook client the AutoDiscover service is available via our 'remote.domain'.com'  WAN address.

Your SRV record will look similar to this   ' _autodiscover._tcp SRV 0 0 443 remote.domain.com. '

The actual publishing methods are very similar, however if you want to use the SRV record make sure you do NOT have any public DNS records that match the predefined auto discover URL strings, or your Outlook Client will not search for the SRV record.


Configure Autodiscovery with a DNS SRV record

We only need to add one new rule for Autodiscovery when using the SRV record method.

  1. Right click the firewall policy, click new, exchange web client publishing rule.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  2. Name your rule : SBS Outlook 2007 AutoDiscover click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  3. Use the drop down list to select exchange 2007, and select the tick box for outlook anywhere, and tick the additional folders box. click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  4. Set to publish a single website or load balancer click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  5. Set to connect to the published server using SSL connections, click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  6. On the internal site name page, add your internal site name click next.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  7. On the public name page, add your external site name - in this rule enter 'remote.domain.com' click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  8. On the select web listener page, select your exchange web listener click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  9. On the authentication delegation page set authentication delegation to 'no authentication delegation but client may authenticate directly' click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  10. On the user sets page remove 'authenticated users' and add 'all users' click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  11. Click finish to complete the rule wizard.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

  12. Remove all paths except '/autodiscover/*'
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  13. Click ok to close properties.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

This rule must be ABOVE your existing rule for SBS Outlook Anywhere

On your outlook client start the new account wizard, enter your name and email address details and click Next. You will be prompted with a message saying 'Allow this website to configure [email protected]' server settings' click Allow, and also click on the check box that says don't ask me again, otherwise it will prompt you, repeatedly!!

Next you are prompted to login using your domain credentials then after a few moments the Auto Discover wizard will show you three green ticks, and you can click Finish.

Your mailbox will now open up!


Configure Autodiscovery with a DNS A (host) Record

  1. Right click the firewall policy, click new, exchange web client publishing rule.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  2. Name your rule : SBS Outlook 2007 AutoDiscover click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  3. Use the drop down list to select exchange 2007, and select the tick box for outlook anywhere, and tick the additional folders box. click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  4. Set to publish a single website or load balancer click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  5. Set to connect to the published server using SSL connections, click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  6. On the internal site name page, add your internal site name click next.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  7. On the public name page, add your external site name - in this rule enter 'autodiscover.domain.com' click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  8. On the select web listener page, select your exchange web listener click next
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  9. On the authentication delegation page set authentication delegation to 'no authentication delegation but client may authenticate directly' click next.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  10. On the user sets page remove 'authenticated users' and add 'all users' click next.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  11. Click finish to complete the rule wizard.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  12. Now we must edit the properties of the rule. Go to the properties of the rule, switch to the paths tab.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  13. Remove all paths except '/autodiscover/*'
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  14. Click ok to close properties.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

This rule must be ABOVE your existing rule for SBS Outlook Anywhere

DNS A (Host) Editing the existing Autodiscovery Rule

  1. Now find your existing rule 'SBS outlook anywhere web publishing rule' right click this rule and click properties.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  2. Go to the public name tab, click add.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006
  3. Enter the name 'autodiscover.domain.com' and click ok. click ok to close the properties

    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

  4. Click apply to save the changes to your firewall configuration.
    How to set up Autodiscovery for Outlook 2007 with ISA Server 2006

On your outlook client start the new account wizard, enter your name and email address details and click Next. You will be prompted first to accept a certificate warning and then prompted to login using your domain credentials then after a few moments the AutoDiscover wizard will show you three green ticks, and you can click Finish.

Your mailbox will now open up!

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