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White Paper: Understanding the Exchange 2010 Autodiscover Service

 

Topic Last Modified: 2012-09-09

Patricia Eddy, Senior Writer, Exchange

August 2012

This white paper provides detailed information about the Microsoft Exchange 2010 Autodiscover service. It also includes information about how to configure this service in various deployment scenarios. Use the conceptual information and procedures in this white paper to help you deploy the Autodiscover service.

Microsoft Exchange Server 2010

Table of Contents

Microsoft Exchange 2010 includes a service, introduced in Exchange 2007, called the Autodiscover service. The Autodiscover service configures and maintains server settings for client computers that are running Microsoft Outlook and many mobile devices. An important function of the Autodiscover service is to provide access to features for clients that are connected to your messaging environment. These features include the web-based offline address book (OAB), the Availability service, and Unified Messaging (UM). The Autodiscover service must be deployed and configured correctly for clients to automatically connect to features. For more information about how to configure features, see How to configure Exchange services for the Autodiscover service later in this white paper.

When you install the Client Access server role on a computer that is running Exchange 2010, a new virtual directory named Autodiscover is created under the Default Web Site in Internet Information Services (IIS). This virtual directory handles Autodiscover service requests from clients in the following circumstances:

  • When a new Outlook profile is configured or updated

  • When a client periodically checks for changes to the Web Services URLs

  • When underlying network connection changes occur in your messaging environment

Additionally, a new service connection point (SCP) object is created for each server where the Client Access server role is installed. The SCP object is used by domain-connected clients to locate the Autodiscover service. The SCP object contains two pieces of information, the serviceBindingInformation attribute and the keywords attribute. The serviceBindingInformation attribute has the fully qualified domain name (FQDN) of the Client Access server in the form of https://cas01.contoso.com/autodiscover/autodiscover.xml, where cas01.contoso.com is the FQDN for the Client Access server. The keywords attribute specifies the sites to which this SCP record is associated. By default, this attribute specifies the site to which the Client Access server belongs. When a domain-connected client connects to the directory service, the Exchange 2010 client authenticates to and tries to locate the Autodiscover SCP objects that were created during setup by using the user's credentials. In deployments that include multiple Client Access servers, an Autodiscover SCP record is created for each Client Access server. By using the user credentials, the client authenticates to and searches for the Autodiscover SCP objects. After the client obtains and enumerates the instances of the Autodiscover service, the client connects to the first Client Access server in the enumerated and sorted list and obtains the profile information in the form of XML data that is needed to connect to the user's mailbox and available features.

An Outlook 2007 or Outlook 2010 client connects to the Autodiscover service as follows:

  1. Outlook sends a Lightweight Directory Access Protocol (LDAP) query to Active Directory looking for all available SCP objects. Specifically, Outlook initializes the LDAP connection using the ldap_init() function and passes a NULL value for the hostname. When a particular global catalog server name (or domain name) is not specified, the operation searches for a global catalog server in the domain, based on the membership of the computer that is initializing the operation.

  2. Outlook sorts and enumerates the returned results based on the client's site by using the keyword attribute of the SCP record. One of two lists is created, an in-site list or an out-of-site list. The in-site list provides the SCP records that have AutodiscoverSiteScope information. AutodiscoverSiteScope is a parameter that is set on the Client Access server by using the Set-ClientAccessServer cmdlet. The parameter specifies the site for which the Autodiscover service is authoritative. The AutodiscoverSiteScope information contained in the SCP records for the in-site list matches the site for the Outlook client. If there are no in-site records, an out-of-site SCP record list will be generated. The list is not sorted in any particular order. Therefore, the list is approximately in the order of oldest SCP records (based on creation date) first.

    tipTip:
    In environments where Outlook 2007 is deployed in remote sites that do not have Exchange 2010 Mailbox and Client Access servers, you can use site affinity to configure the SCP objects for Outlook clients to use SCP objects that are physically closer. For more information, see Configuring the Autodiscover service to use site affinity later in this white paper.
  3. Outlook first tries to connect to each Autodiscover URL that it previously generated from either an in-site list or an out-of-site list. If that doesn't work, Outlook will try to connect to the predefined URLs (for example, https://autodiscover.contoso.com/autodiscover/autodiscover.xml) by using DNS. If that fails also, Outlook will try the HTTP redirect method and, failing that, Outlook will try to use the SRV record lookup method. If all lookup methods fail, Outlook will be unable to obtain Outlook Anywhere configuration and URL settings.

  4. The Autodiscover service queries Active Directory to obtain the connection settings and URLs for the Exchange services that have been configured.

  5. The Autodiscover service returns an HTTPS response with an XML file that includes the connection settings and URLs for the available Exchange services.

  6. Outlook uses the appropriate configuration information and connection settings to connect to your Exchange messaging environment.

For more information about SCP objects, see “Publishing with Service Connection Points.”

When Outlook is started on a client that is not domain-connected, it first tries to locate the Autodiscover service by looking up the SCP object in Active Directory. Because the client is unable to contact Active Directory, it tries to locate the Autodiscover service by using Domain Name System (DNS). In this scenario, the client will determine the right side of the user’s email address, that is, contoso.com, and check DNS by using two predefined URLs. For example, if your SMTP domain is contoso.com, Outlook will try the following two URLs to try to connect to the Autodiscover service:

  • https://contoso.com/autodiscover/autodiscover.xml

  • https://autodiscover.contoso.com/autodiscover/autodiscover.xml

importantImportant:
For Outlook to be able to locate the Autodiscover service by using DNS, there must be a host record in DNS for the Autodiscover service that maps the entry point, or public IP address, to the Client Access server where the Autodiscover service is hosted.

There is another option related to DNS that is made possible with an Outlook 2007 software update and with Outlook 2010. With this update to Outlook 2007, or with Outlook 2010, the clients will perform an additional check for a DNS SRV record to locate the Autodiscover service that does not require multiple web sites and IP addresses or a new Unified Communications Secure Sockets Layer (SSL) certificate. Although this still requires that you add a DNS record in DNS for the Autodiscover service, you do not have to use a certificate that supports multiple DNS names or have to administer a second website.

For more information about this software update for Outlook 2007, see Microsoft Knowledge Base article 940881, A new feature is available that enables Outlook 2007 to use DNS Service Location (SRV) records to locate the Exchange Autodiscover service. To obtain this update, see Microsoft Knowledge Base article 939184, Description of the update rollup for Outlook 2007: June 27, 2007.

The Autodiscover service makes it easier to configure and manage deployment of Outlook clients. Versions of Exchange Server prior to Exchange 2007, and versions of Outlook prior to Outlook 2007, required that you configure all user profiles manually. Extra work was required to manage these profiles if changes occurred to the messaging environment. Otherwise, the clients could stop functioning correctly.

The Autodiscover service uses a user's email address and domain account to automatically configure the user's profile. By using the email address and domain account, the Autodiscover service can provide the following information to the client:

  • The user’s display name

  • Separate connection settings for internal and external connectivity

  • The location of the user’s Mailbox server

  • The URLs for various features that govern such functionality as Availability (free/busy) information, the Out of Office Assistant, Unified Messaging, and the web-based offline address book

  • Outlook Anywhere server settings

To start to communicate with the Exchange messaging infrastructure, Outlook sends an HTTP POST command to the Autodiscover service. This command includes XML data that requests the connection settings and URLs for the Exchange services that are associated with the Outlook provider. This information is created and stored in Active Directory both during Exchange 2010 Setup and when you configure your Exchange features by using the Exchange Management Shell or the Exchange Management Console.

The Autodiscover service sends the request to the Outlook provider, which then uses the Services Discovery API to retrieve the values in Active Directory. After the values have been returned, the data is passed to the Autodiscover service, which returns the information to the client in an HTTP response. This HTTP response contains the relevant values in XML.

There are three Outlook provider settings, as follows:

  • The WEB setting contains the best URL for Outlook Web App for the user to use. This setting is not required for Exchange 2007.

  • The EXCH setting references the Exchange RPC protocol that is used internally. This setting includes port settings and the internal URLs for the Exchange services that you have enabled.

  • The EXPR setting references the Exchange HTTP protocol that is used by Outlook Anywhere. This setting includes the external URLs for the Exchange services that you have enabled, which are used by clients that access Exchange from the Internet.

The connection settings that the Outlook client uses are translated into MAPI properties. These properties are stored in the user's profile located in the registry on their local computer. However, the URLs for the available Exchange services are cached in the memory of the local computer.

Outlook 2007 and Outlook 2010 automatically connect to the Autodiscover service under the following conditions:

  • Every time that the application starts

  • At intervals on a background thread

  • Any time that the client's connection to an Exchange server fails

There are two parts, which are known as layers, of Outlook that use the Autodiscover service: the Outlook layer and the MAPI layer. The Outlook layer begins operating when you open Outlook to retrieve the user profile settings. These settings are refreshed every time that the Time to Live (TTL) period is specified. The setting for the Time to Live is 60 minutes or whenever an error occurs when Outlook tries to contact an Exchange 2010 server.

If Outlook does not connect to the Autodiscover service, the Outlook layer will reconnect every five minutes because the URLs for the available Exchange services are cached in memory on the local computer. If the client cannot connect to the Autodiscover service, the user cannot use the available Exchange services until the specified URLs are obtained.

By contrast, the MAPI layer connects to the Autodiscover service when there are errors connecting to the Exchange server by using the MAPI protocol. For example, this occurs when the user is using a low-bandwidth network connection or when the user tries to open their mailbox after a mailbox move. The first failure detected by the MAPI layer results in an initial Autodiscover service request. Depending on the type of failure, this request may result in changes to the user's profile. This initial Autodiscover service request is known as the free Autodiscover service request. If no other failures occur after the first failure, the MAPI layer will perform an Autodiscover service request every six hours to update the user's profile settings. The MAPI layer also connects to the Autodiscover service if the user creates a new Outlook profile.

Under most circumstances, Outlook and the Autodiscover service are intended to provide a seamless experience for users. However, there are instances when it may appear that the Autodiscover service is not functioning correctly. The following scenario is an example of when this might occur:

After Exchange Server 2010 is deployed in the messaging environment of the Contoso company, the IT administrator for Contoso upgrades the users to Outlook 2010. The administrator would also like to deploy Outlook Anywhere so that users can access their Exchange information and services from the Internet. To do this, the administrator configures and enables Outlook Anywhere for Exchange 2010. After enabling Outlook Anywhere, the administrator checks the Outlook profile settings on an Outlook 2010 client and notices that the RPC over HTTPS settings were not received by the client. The administrator then runs the test for the Autodiscover service by using the Test E-Mail AutoConfiguration feature in Outlook 2010. The administrator is surprised to see that the Autodiscover service did not create the connection settings in the Outlook profile.

This scenario occurs when the user's Outlook client runs continually. In this example, the Outlook 2010 client successfully connects to the Mailbox server by using TCP/IP. Because no failure was detected, the Autodiscover service does not try to re-create the Outlook profile settings. Outlook uses the initial Autodiscover "free" request that is performed at six-hour intervals.

Because this scenario is possible, Outlook provides a method to force this update to occur. The following procedure describes how to force Outlook to update the user profile settings by using the Autodiscover service.

To manually force the Autodiscover service to update the user’s profile settings, use the following steps:

  1. Open Outlook 2010.

  2. Click Tools, and then click Account Settings.

  3. On the E-mail Accounts page, on the E-mail tab, click Repair.

  4. Follow the steps in the Repair E-mail Account wizard.

One of the most important aspects of a successful Exchange messaging deployment is how you configure your SSL certificates for securing client communication to your Exchange infrastructure. This is because all communication between Outlook clients and the Autodiscover service endpoint, in addition to communication between the Outlook client and Exchange services, occurs over an SSL channel. For this communication to occur without failing, you must have a valid SSL certificate installed. For a certificate to be considered valid, it must meet the following criteria for the Autodiscover service:

  • The client can follow the certificate chain up to the trusted root.

  • The name matches the URL that the client is trying to communicate with.

  • The certificate is current and has not expired.

tipTip:
For domain-connected clients, Outlook 2007 and Outlook 2010 are designed to ignore the first validity check in the previous list. This design enables Outlook 2007 and Outlook 2010 to function without any certificate warnings when Outlook uses the self-signed certificate that is installed by Exchange Setup.

When you install the Client Access server role, Exchange Setup determines whether an SSL certificate has already been installed on the server. If an SSL certificate is not found, Exchange Setup will create a self-signed SSL certificate in Internet Information Services (IIS) that meets validity tests for domain-connected clients. The self-signed certificate has a common name that maps to the NetBIOS name of the server. The self-signed certificate also includes the FQDN of the server as an additional DNS name that is stored in the certificate’s Subject Alternative Name field. This enables domain-connected clients to successfully connect to the Autodiscover service without receiving any certificate warnings if the certificate has not expired and the FQDN of the server you are connecting to is stored in the Subject Alternative Name of the certificate. Although the client is unable to validate the self-signed certificate up to the trusted root, this is the one validity test that is allowed when domain-connected clients connect to the Autodiscover service by using the self-signed certificate.

tipTip:
The Subject Alternative Name field is a special field that is available in X.509 v.3 certificates that lets you add multiple DNS names to a single certificate.

To summarize, the self-signed certificate allows domain-connected Outlook clients to work immediately after Exchange Setup has completed and without any security warnings. However, we do not recommend long-term use of this self-signed certificate because it was primarily intended to ease the urgency of obtaining a correct certificate so that Outlook clients can immediately start to use Exchange 2010 features. However, Outlook Anywhere clients and mobile device users who connect by using Exchange ActiveSync will be unable to connect when referencing a certificate whose common name is the NetBIOS name of the server. Instead, the common name of the certificate must be in the form of an FQDN that maps to the external DNS namespace those clients will be connecting to, for example, mail.contoso.com.

tipTip:
We recommend that you immediately replace the self-signed certificate with a commercially available Internet trusted certificate or a trusted internal public key infrastructure (PKI)-issued certificate.

Because Outlook clients connect to the Autodiscover service by using SSL, this introduces a new challenge. Outlook clients must be able to resolve the DNS namespace, for example, autodiscover.contoso.com, in addition to other externally published Exchange features such as Outlook Web App or Exchange ActiveSync that might reference a different DNS namespace, such as mail.contoso.com. This can all be done by using an SSL certificate that supports Subject Alternative Names. These types of certificates are known as Unified Communications certificates.

Although using a certificate that supports Subject Alternative Names is a recommended solution, there are other solutions you can implement if you cannot deploy a certificate that supports Subject Alternative Names. These scenarios and solutions are discussed in the following sections, starting with the implementation of a Unified Communications certificate.

If you are providing external access to Autodiscover by using Outlook Anywhere (formerly known as RPC over HTTP), you must install a valid SSL certificate on the Client Access server by using one of the following four scenarios. Additionally, you must correctly configure your services, such as the Availability service, before the Autodiscover service can provide the correct external URLs to clients.

When the client tries to connect to your messaging environment, the client locates the Autodiscover service on the Internet by using the right side of the user's email address that was entered. Notice that, for the Autodiscover service to function correctly, this must be the user's primary SMTP address. The Autodiscover service URL will be either of the following URLs:

  • https://<smtp-address-domain>/autodiscover/autodiscover.xml

  • https://autodiscover.<smtp-address-domain>/autodiscover/autodiscover.xml

For example, if the user's e-mail address is kwekua@contoso.com, the Autodiscover service should be located at either https://contoso.com/autodiscover/autodiscover.xml or https://autodiscover.contoso.com/autodiscover/autodiscover.xml. This means that you must add a host record for the Autodiscover service to your external DNS zone.

There are several methods for configuring your Client Access server to support connections to the Autodiscover service from the Internet. You should choose a method after you weigh the advantages and disadvantages associated with the following methods.

We recommend that you provide all the necessary DNS names in the same certificate by using a Unified Communications certificate that supports the Subject Alternative Name field. Using a Unified Communications certificate reduces the complexity of configuring and managing the Autodiscover service and Exchange services URLs. However, using a Unified Communications certificate may increase the cost, as this kind of certificate can be more expensive than the single-name certificates that you already may own.

tipTip:
There are special considerations when you use Unified Communications certificates with Internet Security and Acceleration (ISA) Server 2004 and ISA Server 2006. For more information, see the ISA Server team blog article: Certificates with Multiple SAN Entries May Break ISA Server Web Publishing and Microsoft Knowledge Base article 841664, Clients may receive an "Error Code 500 Internal Server Error" error message when they try to visit a Web site that you publish by using ISA Server 2006 or ISA Server 2004.

A list of third-party certification authorities (CAs) that currently support Subject Alternative Names is documented in Microsoft Knowledge Base article 929395, Unified Communications Certificate Partners.

You could also install Windows Certificate Services and create and install your own SSL certificate that includes multiple DNS names. Although this may be the least expensive approach at first, you will incur the additional administrative overhead of distributing and maintaining the root certificates to your users so that clients that are not domain-connected can follow the certificate chain up to the trusted root certificate store. Additionally, your Outlook Anywhere users must manually install the root certificate on their remote workstations and Exchange ActiveSync users must manually install the root certificate on their mobile devices.

Although certificates that support Subject Alternative Names are highly recommended, they are not required. Another recommended solution is to use one single-name certificate installed on the Default Web Site.

importantImportant:
In this scenario, you must update the Autodiscover URL in the SCP object in Active Directory and the internal URLs for the Exchange services so that Outlook clients do not receive the following error: The name of the security certificate is invalid or does not match the name of the site.
This warning message, and how to correct it, is documented in Microsoft Knowledge Base article 940726, Warning message when you start Outlook 2007 and then connect to a mailbox that is hosted on a server that is running Exchange 2007 or Exchange 2010: "The name of the security certificate is invalid or does not match the name of the site".

If your DNS provider supports SRV records, this solution is the simplest and least expensive way to deploy Outlook Anywhere in hosted and non-hosted Exchange 2010 environments. For more information, see Microsoft Knowledge Base article 940881, A new feature is available that enables Outlook 2007 to use DNS Service Location (SRV) records to locate the Exchange Autodiscover service, and Microsoft Knowledge Base article 939184, Description of the update rollup for Outlook 2007: June 27, 2007.

Sometimes you cannot use a certificate that supports multiple DNS names. For example, this may occur if you want to replace the self-signed certificate with a preexisting certificate exported from an earlier version of Exchange, or if you have already purchased a new single-name certificate before fully understanding the certificate requirements for the Autodiscover service for Exchange 2010. If this describes your situation, there are alternative solutions you can implement to address these types of scenarios that will ultimately give you the same level of functionality. One option is to obtain a second certificate and install it on a second website that will be specifically used for Autodiscover.

In this scenario, one certificate is issued with the common name that is used as the entry point for clients that connect from the Internet, for example, mail.contoso.com. The second certificate has a common name that references the FQDN for the Autodiscover service, for example autodiscover.contoso.com. This option requires two separate websites and public IP addresses. The Default Web Site will host your primary Exchange features and services such as Outlook Web App and Exchange ActiveSync while the second website will be used to host the Autodiscover service.

If you cannot, or do not want to use Scenario 2: Using one single-name certificate and the Autodiscover SRV record described earlier in this white paper, this kind of deployment scenario may be the ideal solution to use in situations such as a hosted Exchange 2010 environment. Using the Autodiscover service with redirection may be the ideal solution because some DNS providers do not support SRV records. However, this kind of deployment can also be used for organizations that are not hosting multiple domains. With this option, you install a single-name certificate on the Default Web Site and create another website that contains no certificate. Domain-connected clients continue to locate the Autodiscover service by using the SCP object and will not receive any security warnings as long as the URL for connecting to the Autodiscover service that is stored in the SCP object has been changed to refer to the FQDN of the certificate installed on the Default Web Site. Clients that connect from the Internet will at first be unable to find Autodiscover by using DNS, as described in How the Autodiscover service works with clients earlier in this white paper. However, before failing to connect to the Autodiscover service, Outlook will try an additional method to connect to the Autodiscover URL by using HTTP (instead of HTTPS) and connect to the Autodiscover website and then be redirected to the Autodiscover service hosted under the Default Web Site. When these Internet-based Outlook clients connect to this redirection site, they will see a dismissible warning messaging asking them to verify that they are being redirected to a trusted URL. In this case, you must advise your users to accept this warning message and allow Outlook to connect to this trusted URL.

tipTip:
Similar to using two single-name certificates, this solution also requires a second public IP address that must be assigned to the second website.

All the previous scenarios are supported by Microsoft but vary in complexity. The effort involved in implementing and managing each solution over the long term may result in increased total cost of ownership depending on your environment. The following table illustrates the pros and cons associated with each solution.

 

Scenario Pros Cons

Single certificate that supports multiple DNS names

  • Easy to implement

  • Supports all client connections

  • Microsoft-recommended best practice

  • Higher cost certificate type (Unified Communications certificate)

  • Requires additional configuration if used together with either ISA Server 2004 or ISA Server 2006

One single-name certificate and website

  • Easy to implement

  • Supports all client connections

  • Least expensive

  • Ideal for hosters if DNS provider supports SRV records

Two single-name certificates and websites

  • Lower cost than using Unified Communications certificate

  • Both sites are secured with SSL

  • Requires an additional public IP address

  • Complex to set up and maintain

Single certificate with redirect

  • Can be done by using your existing certificate

  • No additional cost

  • Ideal for hosters if DNS provider does not support SRV records

  • Requires an additional public IP address

  • Somewhat complex to set up

Single certificate generated by using Windows Certificate Services

  • Smallest upfront cost

  • Supports all client connections

  • Highest total cost of ownership for administrators and end users

importantImportant:
Whichever solution you implement to replace the default self-signed certificate, your internal Outlook 2007 and Outlook 2010 users may report that they receive the following security warning when they start Outlook: The name of the security certificate is invalid or does not match the name of the site.
For more information about this security warning, see Microsoft Knowledge Base article 940726, Warning message when you start Outlook 2007 and then connect to a mailbox that is hosted on a server that is running Exchange Server 2007 or Exchange Server 2010: "The name of the security certificate is invalid or does not match the name of the site".

This section describes how to configure the Autodiscover service in the following four scenarios:

  • Scenario 1: Using a certificate that supports multiple DNS names

  • Scenario 2: Using one single-name certificate

  • Scenario 3: Using two single-name certificates

  • Scenario 4: Using the Autodiscover service with redirection

The following table lists the requirements for each scenario.

 

Requirements Scenario 1 Scenario 2 Scenario 3 Scenario 4

Primary IP address

Yes

Yes

Yes

Yes

Secondary IP address

No

No

Yes

Yes

Primary public IP resolving to Default Web Site*

Yes

Yes

Yes

Yes

Secondary public IP resolving to Autodiscover website**

No

No

Yes

Yes

# of certificates

1

1

2

1

Modification of SCP object

No

Yes

Yes

Yes

Modification of Web services URLs

No

Yes

Yes

Yes

*Must resolve to the host name that users use to connect to Exchange services, for example, mail.contoso.com.

**Must resolve to the FQDN for the Autodiscover service, for example, autodiscover.contoso.com.

This section discusses how to configure the Autodiscover service that uses either a Unified Communications certificate or a certificate created internally by using Windows Certificate Services. We recommend that you use a Unified Communications certificate that supports Subject Alternative Names.

The list of third-party certification authorities (CAs) that currently support Subject Alternative Names is documented in Microsoft Knowledge Base article 929395, Unified Communications Certificate Partners.

The following procedures describe how to create a certificate request for submission to a third-party CA and when to use your own internal PKI by using Windows Certificate Services.

You’ll need to create the certificate request for submission to your third-party certification authority (CA). On the Client Access server, open the Exchange Management Shell and enter the following code.

New-ExchangeCertificate -GenerateRequest -DomainName mail.contoso.com, autodiscover.contoso.com -FriendlyName contosoinc -KeySize 1024 -PrivateKeyExportable:$True -SubjectName "c=US o=contoso inc, CN=server01.contoso.com" 

importantImportant:
If your internal DNS namespace differs from your external namespace, you will want to add more DNS names to the DomainNames parameter. For example, you might enter something similar to the following: New-ExchangeCertificate -GenerateRequest -DomainName mail.contoso.com, autodiscover.contoso.com, server01.contoso.local, server01 -FriendlyName contosoinc -KeySize 1024 -PrivateKeyExportable:$True -SubjectName "c=US o=contoso inc, CN=server01.contoso.com"
tipTip:
You may be asked to include additional parameters or may be confused about what to enter for the SubjectName. Confirm the required parameters and necessary information with the CA vendor.
importantImportant:
Make sure to include the PrivateKeyExportable parameter and set the value to $true if you plan to use the certificate on additional Client Access servers and ISA Server computers.

After you request the certificate, see "Step 2: Install the Certificate" later in this section.

In Exchange 2007, the New-ExchangeCertificate cmdlet allowed you to save the certificate request to a file that you specified using the –Path parameter. In Exchange 2010, you must either copy the output of the New-ExchangeCertificate cmdlet or use the following syntax to send the data to a file.

$Data = New-ExchangeCertificate -GenerateRequest -DomainName mail.contoso.com, autodiscover.contoso.com,  server01.contoso.local, server01 -FriendlyName contosoinc -KeySize 1024 -PrivateKeyExportable:$True -SubjectName "c=US o=contoso inc, CN=server01.contoso.com"

Then run the following cmdlet to save the information stored in the Data variable to a file.

Set-Content -path "C:\Docs\MyCertRequest.req" -Value $Data

You can use Windows Certificate Services to create and manage your own SSL certificates. For additional details about how to manage your own Public Key Infrastructure for Windows Server 2003, see the following resources:

  • Public Key Infrastructure for Windows Server 2003

  • Best Practices for Implementing a Microsoft Windows Server 2003 Public Key Infrastructure

To create a certificate request internally by using Windows Certificate Services, use the following steps:

  1. If you have not already done this, install Windows Certificate Services on a server that is running Windows Server 2003 in your messaging infrastructure.

  2. On a server that is running Windows Server 2003, open Add/Remove Windows Components and install Certificate Services.

    tipTip:
    During installation of Certificate Services, you will be prompted to select the type of CA to install. Select the option to install an Enterprise CA and complete the wizard.
  3. To create the certificate request, on the Client Access server, open the Exchange Management Shell and enter the following:

    New-ExchangeCertificate -GenerateRequest -DomainName mail.contoso.com, autodiscover.contoso.com -PrivateKeyExportable:$True
    
    importantImportant:
    The first DNS name following the DomainName parameter will automatically become the common name associated with the certificate. Be certain that you enter the FQDN that users will use to connect to services including Outlook Web App, Exchange ActiveSync, and Outlook Anywhere. See the previous note regarding how to save the certificate request to a file.
    tipTip:
    If your internal DNS namespace differs from your external namespace, you will want to add more DNS names to the DomainNames parameter. For example, you might enter something similar to the following:
    New-ExchangeCertificate -GenerateRequest -DomainName mail.contoso.com, autodiscover.contoso.com, machinename, machinename.contoso.local -PrivateKeyExportable:$True 
    
    
  4. On your Client Access server, open Internet Explorer and enter the URL to connect to the Certificate Services administration webpage that is hosted on the server where you installed Certificate Services. For example, http://CAS01/certsrv or https://CAS01/certsrv.

  5. Click Request a certificate, click Advanced certificate request, and then click Submit a certificate request by using a base-64-encoded CMC or PKCS #10 file.

  6. Copy the contents of the certreq.txt file that you saved in step 3 or the output of the New—ExchangeCertificate cmdlet in the Saved Request field.

  7. Click Web Server under Certificate Template and click Submit.

  8. Click Download certificate and then save the CER file to Drive C, that is c:\certnet.cer.

The following procedure describes how to import and enable a third-party certificate or one that you created internally by using Windows Certificate Services. The process is the same for each.

tipTip:
The Import-ExchangeCertificate cmdlet installs the certificate in the Personal certificate store on the server and the Enable-ExchangeCertificate cmdlet installs the certificate on the website.

To install and enable an SSL certificate, open the Exchange Management Shell on the Client Access server and run the following command.

Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content -Path c:\certnew.cer.-Encoding byte -ReadCount 0)) -Password:(Get-Credential).password
| Enable-ExchangeCertificate  -Services iis

Domain-connected clients will typically obtain the root certificate automatically by using a Group Policy. However, there are circumstances when this may not work correctly. If domain-connected clients cannot automatically install the root certificate, you can manually configure a group to distribute certificates that will be trusted by all member computers of the domain. For more information about how to add a trusted root CA to a Group Policy object, see Add a trusted root certification authority to a Group Policy object.

importantImportant:
Installing a root certificate on a mobile device requires that you connect the device with your Windows operating system. If you are running Windows XP, you must install the latest version of the desktop ActiveSync application. If you are running Windows Vista or Windows 7, you can use the integrated Windows Mobile Device Center in Control Panel, but you must first download the Windows Mobile Device Center application.

To obtain the root certificate from Certificate Services, use the following steps:

  1. Open Internet Explorer on a domain-connected computer, and then enter the URL to connect to the Certificate Services administration webpage.

  2. Select the Download a CA certificate, certificate chain or CRL option, and then select Download a CA certificate.

  3. Save the .cer file to the desktop and name the .cer file root.cer.

  4. Distribute the CER file to your remote users by using email, an FTP site, or other method.

To install the SSL certificate on your Outlook 2007 and Outlook 2010 clients, use the following steps:

  1. Copy the root certificate to the desktop.

  2. Select the root certificate and open it.

  3. In the Certificate dialog box, on the General tab, click Install Certificate.

  4. In the Certificate Import Wizard, click Next.

  5. Click Place all certificates in the following store and then click Browse.

  6. In the Select Certificate Store window, click Trusted Root Certification Authorities and then click OK.

  7. Click Next and then click Finish.

In most cases, you will already have a host record in external DNS for the host name that your users will be using to connect to your Exchange messaging infrastructure by using Outlook Web App, Exchange ActiveSync or Outlook Anywhere. For example, mail.contoso.com. For the Autodiscover service to function correctly, you must add an additional host record so that Outlook 2007 and Outlook 2010 clients can locate and connect to the Autodiscover service when they use the Outlook Anywhere feature from the Internet. The host record you create should map to the public IP address that will be used as the entry point to your Client Access server.

Now that you have configured SSL for your Autodiscover service deployment scenario, you must configure your Exchange services for external access. For more information, see How to configure Exchange services for the Autodiscover service later in this white paper.

After you configure Exchange to use an SSL certificate that supports multiple DNS names and modify the Exchange services URLs as needed, the domain-connected clients will reference the internal URLs for the Exchange services that were automatically set when the Client Access server role was installed. Clients that are not domain-connected will connect by using the external URLs that you entered as part of this procedure. If your certificate includes all the necessary DNS names, both domain-connected and non-domain-connected clients will be able to successfully connect to the Autodiscover service without receiving security warnings that result from mismatched names. Domain-connected clients will locate the Autodiscover service by referencing the SCP object. Conversely, clients that are not domain connected will not locate the SCP object and will fail over to using DNS.

This section describes how to use one single-name certificate where the common name of the certificate references the host name users will use to connect to Exchange from the Internet, for example, mail.contoso.com.

The procedures in the following section assume that you already have obtained a valid third-party SSL certificate that uses the common name your users will be using to connect to your Exchange messaging infrastructure. The first option describes how to use a preexisting certificate that you would export from an existing Exchange server that runs an earlier version of Exchange. The second option describes how to use a new third-party certificate.

If you must create a certificate request, see "Step 2: Install the Certificate" in the Scenario 1: How to use a certificate that supports multiple DNS names section earlier in this white paper.

The following procedures describe how to use an existing SSL certificate that you have already implemented for a version of Exchange prior to Exchange Server 2007. Instructions for exporting a certificate on Exchange 2007 are also provided. To use an existing SSL certificate from a version of Exchange prior to Exchange 2007, use the following steps.

  1. In IIS Manager, open the properties of the Default Web Site, and then click the Directory Security tab.

  2. Click Server Certificate.

  3. In the Web Server Certificate Wizard, select the Export the current certificate to a .pfx file option, and then click Next.

  4. Name the file, and then save it to a location that you will use later.

  5. Enter a password and click Next, then click Next again and click Finish.

  6. Import the certificate to the Personal Store by using the following steps:

    1. In the Certificates snap-in for MMC, expand the top-level Certificates (Local Computer).

    2. Open the options menu of the Personal node, click All Tasks, and then click Import.

    3. In the Certificate Import Wizard, click Browse, locate the .pfx file that you copied to the Client Access server, and then click Next.

    4. Enter the password that you applied to the .pfx file and then select the check box for Mark this Key as Exportable.

    5. Click Place all certificates in the following store, click Personal Certificate Store, click Next, and then click Finish.

  7. Determine the Thumbprint attribute of the imported certificate. To do this, open the Exchange Management Shell and run the following command.

    Get-ExchangeCertificate | fl
    
  8. Locate the certificate that you just imported, copy the certificate’s thumbprint, and then run the following command.

    Enable-ExchangeCertificate -Thumbprint <thumbprint_of_new_certificate> -Services iis
    
    

To use an existing SSL Certificate from Exchange 2007, use the following steps:

  1. On the Client Access server, open the Exchange Management Shell and then run the following command. This will return a list of all existing certificates. You will then need to copy the thumbprint value of the certificate you need.

    Get-ExchangeCertificate -DomainName mail1.contoso.com
    
  2. Using the thumbprint you obtained in step 1, export the certificate to a file. The thumbprint value shown is provided for example purposes only.

    Export-ExchangeCertificate -Thumbprint 5113ae0233a72fccb75b1d0198628675333d010e -BinaryEncoded:$true -Path c:\certificates\export.pfx -Password:(Get-Credential).password
    
    

You can use the Exchange Management Shell on your Client Access server to install and enable your new third-party certificate with the following code.

Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content -Path c:\certificates\ExportedCert.pfx -Encoding byte -ReadCount 0)) -Password:(Get-Credential).password | Enable-ExchangeCertificate  -Services iis

By default, the URL for the Autodiscover service stored in the SCP object in Active Directory will reference the internal FQDN for the Client Access server during Exchange 2010 Setup. You will use the Set-ClientAccessServer cmdlet to modify this URL so that it points to the new location (FQDN) for the Autodiscover service. In the Exchange Management Shell, run the following command.

Set-ClientAccessServer -identity <servername> -AutodiscoverServiceInternalUri https://autodiscover.contoso.com/autodiscover/autodiscover.xml
importantImportant:
You must repeat this step for every Client Access server that is installed in your Exchange messaging infrastructure.

Now that you have configured SSL for your Autodiscover service deployment scenario, you must configure your Exchange services for external and internal access. For more information, see How to configure Exchange services for the Autodiscover service later in this white paper.

Because this solution uses one single-name certificate, clients that are not domain-connected that run Outlook 2007 and Outlook 2010 will receive a security warning when they connect to the Autodiscover service. If your external DNS provider supports Autodiscover SRV records, you can address this issue with an Outlook 2007 software update. Outlook 2010 includes this update. When this software update is applied, Outlook 2007 clients will perform an additional check for a DNS SRV record to locate the Autodiscover service that does not require multiple websites and IP addresses or a new Unified Communications SSL certificate. Although this still requires you to add a DNS record in DNS for the Autodiscover service, you will not have to use a certificate that supports multiple DNS names or have to administer a second website.

For more information about this software update for Outlook 2007, see Microsoft Knowledge Base article 940881, A new feature is available that enables Outlook 2007 to use DNS Service Location (SRV) records to locate the Exchange Autodiscover service. To obtain this update, see Microsoft Knowledge Base article 939184, Description of the update rollup for Outlook 2007: June 27, 2007. Outlook 2010 contains this functionality, so no update is required for Outlook 2010 clients.

In this scenario you installed a single-name certificate where the common name of the certificate references the host name users will use to connect to Exchange from the Internet, for example, mail.contoso.com. This solution required that you modify the SCP and the internal URLs of the Exchange services because the FQDN on the certificate differs from the FQDN referenced in the SCP and the internal URLs for the Exchange services.

This solution is most efficient if the following conditions are true:

  • You do not want the additional administrative overhead of managing multiple websites and IP addresses.

  • The certificate does not include a DNS name for the Autodiscover service.

This solution also requires an Outlook 2007 software update that supports Autodiscover SRV records or the use of Outlook 2010 for all of your clients. If your external DNS provider supports SRV records, a client that is not domain-connected will first try to locate the Autodiscover service by using the SCP object. Because the client cannot contact Active Directory, it will fail over and try to locate the Autodiscover service by using the following URLs using DNS: https://contoso.com/autodiscover/autodiscover.xml and then https://autodiscover.contoso.com/autodiscover/autodiscover.xml. This request will then fail over to the HTTP redirect algorithm, and will also be unsuccessful. Finally, the client will try one more method. It will check for an Autodiscover SRV record in DNS, and then connect.

This section describes how to use two single-name certificates, where the common name of one certificate references the host name users will use to connect to Exchange from the Internet, and the common name of the second certificate references the Autodiscover host name, for example, autodiscover.contoso.com. The existing certificate will typically be exported from a legacy Exchange server or will be a certificate that was recently purchased. In either case, you must obtain a second certificate for the Autodiscover website.

The first step in this process involves adding a second IP address to your network adapter on your Client Access server. Use the following steps.

  1. On the Exchange 2010 Client Access server, open the properties of your network adapter.

  2. Click Internet Protocol, and then click Properties.

  3. Click Advanced.

  4. Under IP addresses, click Add, and then, in the TCP/IP Address dialog box, enter an available IP address in the text box for the IP address and click Add.

In most cases, you will already have a host record in external DNS for the host name that users will be using to connect to Exchange from the Internet, for example, mail.contoso.com. You must also add an additional host record for the Autodiscover service so that Outlook clients can find and connect to the Autodiscover service when they use Outlook Anywhere from the Internet. This host record should map to a second public IP address that points to another entry point to your Client Access server.

The following steps are used to create the host record in internal DNS for the host name that is referenced in the common name of the certificate on the Default Web Site.

  1. Open DNS Manager and expand the Forward Lookup Zones container.

  2. Open the context menu for your DNS zone, for example, contoso.com, and then click New Host (A).

  3. Enter “mail” for the host name that is being used on the Default Web Site, for example mail.contoso.com, and then assign it the local IP address that is assigned to the Default Web Site.

tipTip:
If your internal DNS namespace differs from your external namespace, you must create an additional DNS zone that matches your external namespace, and then create the host record within that zone.

The procedures in the following section assume that you already have obtained a valid third-party SSL certificate that uses the common name your users will be using to connect to your Exchange messaging infrastructure. The first option describes how to use a preexisting certificate that you would export from an existing Exchange server that is running an earlier version of Microsoft Exchange. The second option describes how to use a new third-party certificate.

If you must create a certificate request, see "Step 2: Install the Certificate" in the Scenario 1: How to use a certificate that supports multiple DNS names section earlier in this white paper.

The following procedures describe how to use an existing SSL certificate that you have already implemented for a version of Exchange prior to Exchange Server 2007. Instructions for exporting a certificate on Exchange 2007 are also provided. Using IIS Manager on your earlier version of Exchange, export the existing certificate in PFX format by following these steps.

  1. In IIS Manager, open the context menu for the Default Web Site, click Properties, and then click the Directory Security tab.

  2. Click Server Certificate.

  3. In the Web Server Certificate Wizard, select the Export the current certificate to a .pfx file option, and then click Next.

  4. Name the file, and then save it to a location that you will use later.

  5. Enter a password and click Next, then click Next again and click Finish.

  6. Import the certificate to the Personal Store by using the following steps.

    1. In the Certificates snap-in for MMC, expand the top-level Certificates (Local Computer).

    2. Open the context menu for the Personal node, click All Tasks, and then click Import.

    3. In the Certificate Import Wizard, click Browse, locate the .pfx file that you copied to the Client Access server, and then click Next.

    4. Enter the password that you applied to the .pfx file and then select the check box for Mark this Key as Exportable.

    5. Click Place all certificates in the following store, click Personal Certificate Store, click Next, and then click Finish.

  7. Determine the Thumbprint attribute of the imported certificate. To do this, open the Exchange Management Shell and run the following command.

    Get-ExchangeCertificate | fl
    
  8. Locate the certificate that you just imported, copy the certificate’s thumbprint, and then run the following command.

    Enable-ExchangeCertificate -Thumbprint <thumbprint_of_new_certificate> -Services iis
    
    

To use an existing SSL certificate from Exchange 2007, use the following steps.

  1. On the Client Access server, open the Exchange Management Shell and then run the following command. This will return a list of all existing certificates. You will then need to copy the thumbprint value of the certificate you need.

    Get-ExchangeCertificate -DomainName mail1.contoso.com
    
  2. Using the thumbprint you obtained in step 1, export the certificate to a file. The Thumbprint value shown is provided for example purposes only.

    Export-ExchangeCertificate -Thumbprint 5113ae0233a72fccb75b1d0198628675333d010e -BinaryEncoded:$true -Path c:\certificates\export.pfx -Password:(Get-Credential).password
    
    

You can use the Exchange Management Shell on your Client Access server to install and enable your new third-party certificate with the following code.

Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content -Path c:\certificates\ExportedCert.pfx -Encoding byte -ReadCount 0)) -Password:(Get-Credential).password | Enable-ExchangeCertificate  -Services iis

The next step in this process is to configure the Default Web Site by using IIS Manager. Use the following steps.

  1. In IIS Manager, expand Web Sites, open the context menu for the Default Web Site, and then click Properties.

  2. By default, the IP address will be assigned to All Unassigned. Select your primary IP address and assign it to the Default Web Site.

  3. Click Advanced, then Edit, and change the IP assignment for port 443 to the Primary IP address.

The next step in this process is to configure the Autodiscover website by using IIS Manager. Use the following steps.

  1. In IIS Manager, open the context menu for the Web Sites node, click New, and then click Web Site.

  2. When the Web Site Creation Wizard launches, click Next.

  3. On the Web Site Description page, in the Description field, enter a name for your website and click Next.

  4. On the IP Address and Port Settings page, select the second IP address that you added from the drop-down list and then click Next.

  5. On the Web Site Home Directory page, click Browse, select c:\InetPub\wwwroot, and then click OK. Leave the Anonymous access check box selected and click Next.

  6. On the Web Site Access Permissions page, accept the default setting for Read permission, click Next, and then click Finish.

The following procedure in this section assumes that you have already obtained a valid third-party certificate with the common name users will be using to connect to the Autodiscover service, for example, autodiscover.contoso.com. Because the Enable-ExchangeCertificate cmdlet only works for certificates installed on the Default Web Site, you must use IIS Manager to install this certificate on the Autodiscover website. To use the Exchange Management Shell and IIS Manager to install and enable a third party certificate, use the following steps.

  1. In the Exchange Management Shell, enter the following command to import the second certificate into the Personal Certificate store on the server.

    Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content -Path c:\certificates\ExportedCert.pfx -Encoding byte -ReadCount 0)) -Password:(Get-Credential).password
    
    
  2. In IIS Manager, expand Web Sites, from the context menu of the Autodiscover Web Site, click Properties.

  3. On the Directory Security tab, click Server Certificate.

  4. When the Web Server Certificate Wizard opens, click Next.

  5. On the Server Certificate page, click Assign an existing certificate and then click Next.

  6. On the Available Certificates page, select the certificate that was provided by your CA for the Autodiscover website and then click Next.

  7. On the SSL Port page, accept the default setting of 443 and then click Next.

  8. On the Certificate Summary page, confirm the details are correct, click Next and then click Finish to complete the Web Server Certificate Wizard.

After you have configured the new Autodiscover website in IIS, you will use the Exchange Management Shell to create a new Autodiscover virtual directory by running the following command. The name of the website is case-sensitive.

New-AutodiscoverVirtualDirectory -WebSite "Autodiscover Web Site"

By default, the URL for the Autodiscover service stored in the SCP object in Active Directory will reference the internal FQDN for the Client Access server during Exchange 2010 Setup. You will use the Set-ClientAccessServer cmdlet to modify this URL so that it points to the new location (FQDN) for the Autodiscover service. Use the following command.

Set-ClientAccessServer -identity <servername> -AutodiscoverServiceInternalUri https://autodiscover.contoso.com/autodiscover/autodiscover.xml
importantImportant:
You must repeat this step for every Client Access server in your Exchange messaging infrastructure.

Now that you have configured SSL for your Autodiscover service deployment scenario, you must configure your Exchange services for external and internal access. For more information, see How to configure Exchange services for the Autodiscover service later in this white paper.

After you configure Exchange to use two single-name certificates and websites, domain-connected clients will connect to the Autodiscover service that is hosted under the Default Web Site that is found by using the SCP object. Conversely, non-domain-connected clients will locate the Autodiscover service by using DNS and connect to the Autodiscover service hosted under the second website. Because each website contains a valid certificate, all clients should be able to connect without receiving any security warnings.

The following section describes how to configure the Autodiscover service when you use one single-name certificate with an SSL website in addition to a second website responsible for redirecting incoming requests over port 80 to the Autodiscover virtual directory set to accept requests over port 443.

tipTip:
If you are a large-scale hoster and unable to implement Scenario 2, review the optional information that appears after the following steps.
These steps assume that you have already obtained a valid third-party certificate with the common name users will be using to connect to Exchange from the Internet which is installed on the Default Web Site of your Client Access server, for example, mail.contoso.com.

To add a second IP address to your network adapter, use the following steps.

  1. On the Exchange 2010 Client Access server, open the properties of your network adapter.

  2. Click Internet Protocol and then click Properties.

  3. Click Advanced.

  4. Under IP addresses, click Add and then enter an available IP address.

In most cases, you will already have a host record in external DNS for the host name users will be using to connect to Exchange from the Internet, for example, mail.contoso.com. You must add an additional host record for the Autodiscover service so that Outlook clients can find and connect to the Autodiscover service when they use Outlook Anywhere from the Internet. This host record should map to a second public IP address that points to another entry point to your Client Access server. The following procedure describes how to create the required host records in internal DNS.

  1. Open DNS Manager and expand the Forward Lookup Zones container.

  2. Open the context menu for your DNS zone, for example, contoso.com, and then click New Host (A).

  3. Enter "autodiscover" and the second IP address that you already assigned to your network adapter.

  4. Create an additional host record for the host name being used on the Default Web Site, for example.mail.contoso.com, and assign it the local IP address that is assigned to the Default Web Site.

Use the following steps to configure the default website.

  1. In IIS Manager, open the context menu for the Default Web Site and then click Properties.

  2. By default, the IP address will be assigned to All Unassigned. Select your primary IP address and assign it to the Default Web Site.

  3. Click Advanced, and then click Edit and change the IP assignment for port 443 to the primary IP address.

The following steps are used to create a new Autodiscover directory structure that will be used by the Autodiscover redirect website that you create in the next step.

  1. On the Client Access server, open a new Windows Explorer window, and then locate C:\Inetpub.

  2. Create a new folder under c:\Inetpub named Autodiscover.

  3. Create a subfolder under c:\Inetpub\Autodiscover named Autodiscover.

  4. Create a new blank text file, and then name it autodiscover.xml.

Use the following steps to create the Autodiscover redirect website.

  1. In IIS Manager, open the context menu for the Web Sites node, and then click New Web Site.

  2. In the New Web Site Wizard, in the Description box, enter the name of the website, for example, Autodiscover Web Site, and then click Next.

  3. In the IP Address and Port Settings window, select the second IP address that you added and then click Next.

  4. In the Web Site Home Directory window, browse and then select c:\Inetpub\autodiscover, leave the Anonymous access check box selected, and then click Next.

  5. Expand the Autodiscover website and select the Autodiscover virtual directory under the website.

  6. In the right pane, open the context menu for the autodiscover.xml file, and then click Properties.

  7. Select the A redirection to a URL option and enter the URL to the Autodiscover.xml file that is located under the Default Web Site by using the FQDN users will use to connect to Outlook Web App, Exchange ActiveSync, and Outlook Anywhere, for example, https://mail.contoso.com/autodiscover/autodiscover.xml.

By default, the URL for the Autodiscover service stored in the SCP object in Active Directory will reference the internal FQDN for the Client Access server during Exchange 2010 Setup. For internal users who use Outlook 2007, you will use the Set-ClientAccessServer cmdlet to modify the URL so that it references the common name of the certificate on the Default Web Site.

To use the Exchange Management Shell to change the internal URL for the Autodiscover service, run the following code.

Set-ClientAccessServer -AutodiscoverServiceInternalUri https://mail.contoso.com/autodiscover/autodiscover.xml

Now that you have configured SSL for your Autodiscover service deployment scenario, you must configure your Exchange services for external and internal access. For more information, see How to configure Exchange services for the Autodiscover service later in this white paper.

For large-scale hosted environments, using a single redirect website as discussed earlier may not be appropriate. If you expect heavy web traffic, you should consider configuring the Autodiscover service so that incoming requests for the Autodiscover service are managed by individual websites for each domain. These requests can then be redirected for each hosted domain to the Autodiscover virtual directory under the Default Web Site in Internet Information Services (IIS). You may also host the Autodiscover service on a dedicated web server if you want.

In this scenario, you create separate websites, each with its corresponding DNS entries for each hosted email domain. For example, the domain named contoso.no would be called autodiscover.contoso.no, and the domain named contoso.se would be called autodiscover.contoso.se.

To configure this kind of scenario, in IIS Manager, configure redirection for each of your sites by modifying each website’s autodiscover.xml file so that it points to https://mail.contoso.com/autodiscover/autodiscover.xml.

tipTip:
These sites should be configured only for HTTP (port 80) traffic.

After you configure Exchange to use an SSL certificate with redirection, domain-connected clients will continue locating the Autodiscover service by using the SCP object and connect to the Autodiscover service that is hosted under the Default Web Site. On the other hand, clients that are not domain-connected will be unable to locate the SCP object and fail over to using DNS. These clients will also be unable to locate Autodiscover by using the following URLs:

  • https://contoso.com/autodiscover/autodiscover.xml

  • https://autodiscover.contoso.com/autodiscover/autodiscover.xml

The clients will instead use an alternative method: an HTTP redirect. When the redirect happens, the client will receive a redirect from the Autodiscover site to the site that is dedicated to handling email. When this occurs, a warning message is displayed in Outlook that says: Allow this website to configure server settings?

Outlook lets users turn off the option for this warning message to continue to appear. We recommend that you instruct users to turn off the warning message on their clients. Or, you can suppress the Autodiscover redirect warning for HTTP and SRV redirections. To do this, see Microsoft Knowledge Base article 956528, You cannot suppress the Autodiscover redirect warning in Outlook 2007.

If your topology includes multiple sites or forests, other considerations must be addressed when you configure the Autodiscover service to handle these types of deployments. For the Autodiscover service to function correctly, you must make sure that your organization meets the following requirements:

  • You must have at least one Client Access server installed in each Active Directory site where users’ mailboxes reside for your deployment. For features such as the Availability service and Unified Messaging, you must also have the Unified Messaging, Mailbox, and Hub Transport server roles installed in the Exchange messaging environment.

Additionally, if you are not providing external access to your messaging infrastructure, there are several steps in the Autodiscover deployment process that you will not have to perform.

The following sections describe the scenarios and how to deploy the Autodiscover service in each of these scenarios.

If you manage a large, distributed organization that has sites that are separated by low-bandwidth network connectivity, we recommend that you use site affinity for the Autodiscover service for intranet-based traffic. To use site affinity, you specify which sites are preferred for clients to connect to a particular Autodiscover service instance. Specifying which sites are preferred is also known as configuring site scope.

You configure site affinity by using the Set-ClientAccessServer cmdlet. This cmdlet lets you specify the preferred sites for connecting to the Autodiscover service on a specific Client Access server. After you configure site affinity for the Autodiscover service, the client will connect to the Autodiscover service as you specified.

The following example uses a topology that includes one forest with three sites:

  • US-contoso A Contoso site that is located in North America

  • Europe-contoso A Contoso site that is located in Europe

  • APAC-contoso A Contoso site that is located in Asia

In this example, each Active Directory site has Client Access servers and Mailbox servers. The US-contoso site is connected to the Europe-contoso site by using a high-speed connection. The US-contoso site is connected to the APAC-contoso site by using a low-speed connection. The APAC-contoso site is connected to the Europe-contoso site by using a high-speed connection.

Based on these connectivity factors, you might want to allow users in the US-contoso and Europe-contoso sites to use either the Client Access servers in the US-contoso or the Europe-contoso sites, users in the Europe-contoso site to use any Client Access servers in the organization for the Autodiscover service requests, and users in the APAC-contoso site to use the Client Access servers in the APAC-contoso or the Europe-contoso site. Finally, the Client Access servers can be reached by using a common internal namespace across all sites.

You can configure site scope for users in the US-contoso site by configuring the Autodiscover site scope correctly on the Client Access servers in the US-contoso site. To do this, use the following command.

Set-ClientAccessServer -Identity "us-cas" -AutodiscoverServiceInternalURI "https://internal.contoso.com/autodiscover/autodiscover.xml" -AutoDiscoverSiteScope "us-contoso","europe-contoso"

The previous command ensures the following:

  • If an Outlook client is a member of the US-contoso Active Directory site, it will use the US-CAS SCP record for its Autodiscover requests. Additionally, the client will not try to use an APAC-CAS server for Autodiscover requests.

  • If an Outlook client is a member of the Europe-contoso Active Directory site, it can use the US-CAS SCP record for its Autodiscover requests.

You can configure site scope for users in the APAC-contoso site by configuring the Autodiscover site scope property on the Client Access servers in the APAC-contoso site. To do this, use the following command.

Set-ClientAccessServer -Identity "apac-cas" -AutodiscoverServiceInternalURI "https://internal.contoso.com/autodiscover/autodiscover.xml" -AutoDiscoverSiteScope "apac-contoso","europe-contoso"

The previous command ensures the following:

  • If an Outlook client is a member of the APAC-contoso Active Directory site, it will use the APAC-CAS SCP record for its Autodiscover requests. Additionally, the client will not try to use a US-CAS server for Autodiscover requests.

  • If an Outlook client is a member of the Europe-contoso Active Directory site, it can use the APAC-CAS SCP record for its Autodiscover requests.

Finally, because the Client Access servers in the Europe-contoso site are connected to both the US-contoso and APAC-contoso sites by using a high-speed connection, you will want to make sure that users in either of those sites can use the Client Access servers in the Europe-contoso site. To do this, configure the Autodiscover site scope property with the following command.

Set-ClientAccessServer -Identity "europe-cas" -AutodiscoverServiceInternalURI "https://internal.contoso.com/autodiscover/autodiscover.xml" -AutoDiscoverSiteScope "us-contoso", "europe-contoso", "apac-contoso"

The previous command ensures that Outlook clients that are members of the Europe-contoso Active Directory site use the Europe-CAS SCP record for Autodiscover service requests. Additionally, the Outlook client can also use either the US-CAS SCP record or the APAC-CAS SCP record after you run the previous commands.

Therefore, if a user is located in the US-contoso site and tries to locate the Autodiscover service by using Outlook, the Outlook client can select the SCP record from the list in which the site scope equals "us-contoso". In this case, the client will access either a US-CAS server or a Europe-CAS server.

If you do not alter the site-scope settings for the Autodiscover service, the Outlook client will only use the Client Access servers in its local site (US-contoso, Europe-contoso, APAC-contoso). If, on the other hand, you delete the site-scope settings, Outlook will randomly select an SCP record for Autodiscover requests. This could result in a poor experience for the end user because the request may go out of the user's Active Directory site and use a low-quality network connection. For example, if you did not run the previous commands, a user in the US-contoso Active Directory site would potentially use the APAC-CAS server, the Europe-CAS server, or the US-CAS server.

You can use the Set-ClientAccessServer cmdlet in the Exchange Management Shell to configure the Autodiscover service to use site affinity on a computer that is running Exchange 2010 that has the Client Access server role installed. Run the following command.

Set-ClientAccessServer -Identity "ServerName" -AutodiscoverServiceInternalURI "https://internalsitename/autodiscover/autodiscover.xml" AutoDiscoverSiteScope "SiteName"

You can deploy by using multiple forests. Two of the multiple forest deployment scenarios are the resource forest topology and the multiple trusted forest topology. The following sections describe how the Autodiscover service is used in these two deployment scenarios.

If you use a resource forest topology, user accounts reside in one forest (known as a user account forest) and are deployed in a separate forest (known as a resource forest).

In this scenario, the following will occur:

  1. The Outlook client contacts the user account forest to locate the URL for the Autodiscover service. Because the service is hosted in the resource forest, you must update the user account forest to include the information that is required to enable the client to access the resource forest. To do this, you must create an Autodiscover SCP pointer record in the user account forest. The Autodiscover SCP pointer record includes the LDAP URL of the resource forest that the client will use to locate the Autodiscover service in the resource forest.

  2. Outlook binds to the target forest by using the LDAP URL and retrieves the SCP records.

  3. Depending on your SCP record configuration, the following will occur:

    1. If the account forest Active Directory sites are in the resource forest, which requires Microsoft Identity Lifecycle Manager 2007 synchronization, the Outlook client will retrieve the SCP records for the Outlook client's Active Directory site.

    2. If the SCP records do not have a site scope that matches the Outlook client's site, the Outlook client will retrieve an SCP record at random. Also, if the Active Directory site topology is not being replicated between the user account forest and the resource forest, the Outlook client will retrieve an SCP record at random.

  4. The Outlook client connects to the URL that is specified in the SCP record that was obtained and retrieves the required user profile settings by using the Autodiscover service.

tipTip:
To synchronize Active Directory sites between forests, see "Synchronizing Sites and Subnets" in Multiple Forest Considerations in Windows 2000 and Windows Server 2003.

In the multiple trusted forest scenario, the user accounts are deployed in multiple forests. Features such as the Availability service and Unified Messaging rely on the Autodiscover service to access user accounts across forests. In this scenario, the Autodiscover service must be available to users across multiple trusted forests. This scenario resembles the resource forest scenario, except that the Autodiscover SCP object must be configured in all forests. To configure the Autodiscover SCP object in the multiple forest topology, run the Export-AutoDiscoveryConfig cmdlet from each forest that has the Autodiscover service against each target forest where is deployed.

If your deployment has two or more trusted forests, you must update so that users who are running in one forest can access the Client Access servers in the remote (or target) forest to use the Autodiscover service. To do this, you must run the Export-AutodiscoverConfig cmdlet in the resource forest that contains the Client Access servers that provide the Autodiscover service against the target forests. This will configure the SCP information for the Autodiscover pointer in Exchange 2010. Or, you can manually create the root Autodiscover SCP record container in the user forest.

To use the Exchange Management Shell to configure the Autodiscover service for multiple forests, use the following steps.

  1. On a Client Access server in the resource forest, enter the user name and password for the account that has the required permissions for the target forest in the variable "$a" by running the following command:

    $a = Get-Credential
    
  2. On a Client Access server in the resource forest, run the following command:

    Export-AutoDiscoverConfig -DomainController <FQDN> -TargetForestDomainController <String> -TargetForestCredential $a -MultipleExchangeDeployments $true
    
    

Managing the Autodiscover service for users includes performing tasks such as making sure that users will be able to use the Autodiscover service after their mailboxes are moved from one forest to another forest.The following sections describe the common management tasks for the Autodiscover service. Depending on your deployment, some of these procedures may not have to be performed.

You can use the Exchange Management Shell to configure your deployment to handle mailboxes that are moved from one forest to another for the Autodiscover service.For a cross-forest mailbox move, the two forests must be trusted. For the Autodiscover service to handle this move, you must configure a mail contact in the original forest where the user's mailbox resided.

When you configure a mail contact, the user will authenticate to the original forest where the mailbox resided, and the user will receive a redirect that uses the new email address. The client will then try to contact the Autodiscover service by using the new email address against the new forest.

For example, contoso.com and fourthcoffee.com are separate, trusted forests and the mailbox for a user is kwekua@contoso.com. This user originally resided in the forest named contoso.com and was moved to the forest named fourthcoffee.com.

For this example, you have to set a contact in mail1.contoso.com by using the following command in the Shell.

New-MailContact -ExternalEmailAddress 'SMTP:kwekua@fourthcoffee.com' -Name 'Kweku Ako Adjei' -Alias 'kwekua' -OrganizationalUnit 'contoso.com/Users' -FirstName 'Kweku' -Initials '' -LastName 'Ako Adjei'

After you configure the contact, when the user connects to contoso.com and uses the contoso.com credentials, the following request is sent to the client.

The client will receive the following redirect response from contoso.com.

The user will then be able to connect to the Autodiscover service by using this new email address in the mail2.contoso.com forest.

To use the Exchange Management Shell to create a new mail contact for the Autodiscover service to handle cross-forest mailbox moves, run the following command.

New-MailContact -ExternalEmailAddress 'SMTP:kwekua@fourthcoffee.com' -Name 'Kweku Ako Adjei' -Alias 'kwekua' -OrganizationalUnit 'contoso.com/Users' -FirstName 'Kweku' -Initials '' -LastName 'Ako Adjei'

This section explains how to configure services, such as the Availability service, for the Autodiscover service on a computer that has the Client Access server role installed.When you enable Outlook Anywhere, you must also configure external access to services for the Autodiscover service. This includes the URLs for the Availability service, Web Services, Unified Messaging (UM), and the offline address book.

If you do not configure the external URL values, the Autodiscover service information that is provided to the client may be incorrect for clients that are connecting from outside your network. They may be able to connect to their mailbox. However, they will be unable to use features such as Out of Office functionality, the Availability service, Unified Messaging, or offline address book downloads.

Generally, the internal URL is configured by Setup and references the internal FQDN of the Client Access server. However, the external URL values are NULL and must be configured by using the virtual directory cmdlet for each component.In this section, you will configure external host name, authentication, and encryption settings for the following Web services:

  • Outlook Anywhere

  • Offline address book

  • Unified Messaging

  • Web Services

If you performed a custom installation of Exchange 2010 and you will not be using an service such as Unified Messaging, you will not have to complete the procedure to configure the external URL for Unified Messaging for the Autodiscover service later in this section. Additionally, if you are not providing external access to your services, you can safely ignore these procedures.

importantImportant:
The following procedures assume that you are using a Unified Communications certificate that supports multiple DNS names, as discussed in Scenario 1: Using a certificate that supports multiple DNS names earlier in this white paper. If you have configured the Autodiscover service by following Scenario 2: Using one single-name certificate and the Autodiscover SRV record or Scenario 3: Using two single-name certificates, you must also modify the internal URL of each Exchange service so that the FQDN in the URL references the common name of the certificate on the Default Web Site. For example, you must set the internal URL to https://mail.contoso.com/ews/exchange.asmx.

To use the Exchange Management Shell to configure the external host name for Outlook Anywhere for the Autodiscover service, run the following command.

Enable-OutlookAnywhere -Server CAS01 -ExternalHostname "mail.contoso.com" -DefaultAuthenticationMethod "Basic" -SSLOffloading:$False

To use the Exchange Management Shell to configure the external URL for the offline address book for the Autodiscover service, run the following command:

Set-OABVirtualDirectory -identity "CAS01\OAB (Default Web Site)" -externalurl https://mail.contoso.com/OAB -RequireSSL:$true 

To use the Exchange Management Shell to configure the external URL for Unified Messaging for the Autodiscover service, run the following command:

Set-UMVirtualDirectory -identity "CAS01\UnifiedMessaging (Default Web Site)" -externalurl https://mail.contoso.com/UnifiedMessaging/Service.asmx  -BasicAuthentication:$True

To use the Exchange Management Shell to configure the external URL for Exchange Web Services for the Availability service and Out of Office services, run the following command:

Set-WebServicesVirtualDirectory -identity "CAS01\EWS (Default Web Site)" -externalurl https://mail.contoso.com/EWS/Exchange.asmx -BasicAuthentication:$True

This white paper provides the necessary information to enable you to deploy and configure the Autodiscover service for your users. Use this information to help you define a deployment strategy for the Autodiscover service to provide your users with the Microsoft Exchange features that you enable.

 
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