Configure Microsoft Exchange

Microsoft Exchange Configuration for Calendar Integration

If you are deploying an on-premise Microsoft Exchange server, complete the procedures in this chapter to configure your Microsoft Exchange for calendar integration between the IM and Presence Service and Microsoft Outlook. You can integrate the IM and Presence Service with each of the following Microsoft deployment types:

Table 1. Microsoft Exchange Configuration for Calendar Integration with the IM and Presence Service

Microsoft Exchange Deployment

Microsoft Configuration

Microsoft Exchange 2016 or 2019

Microsoft Exchange 2016 and 2019 Configuration Task Flow


Note


Testing is performed using the major versions of Microsoft Exchange Server. It is expected that all other cumulative updates of these major versions remain compatible. For example, when we mention Exchange 2016, it indicates that the IM and Presence service supports all Cumulative Updates (CU) released under Exchange 2016.


Microsoft Exchange 2016 and 2019 Configuration Task Flow

Complete these tasks to configure a Microsoft Exchange 2016 or 2019 deployment for Outlook calendar integration with the IM and Presence Service.

Procedure

  Command or Action Purpose

Step 1

Verify Windows Security Settings

Verify your Windows Security Settings for Windows Integrated authentication (NTLM).

Step 2

Set Exchange permissions for your release:

Set the Exchange impersonation permissions for specific users or a group of users.

Step 3

Verify permissions for your release:

Verify that the permissions propagate to the mailbox level and that a specified user can access the mailbox and impersonate the account of another user.

Step 4

Enable Authentication on Exchange 2016 or 2019 Running Windows Server 2016

Basic Authentication, Windows Integrated Authentication, or both must be enabled on the EWS virtual directory (/EWS) for the Exchange Server.

Step 5

Configure Certificates for Exchange Server Task Flow

Complete this task flow to configure certificates for a Microsoft Exchange deployment.

Verify Windows Security Settings

Procedure


Step 1

On the Windows domain controller and server(s) running Exchange, choose Start > Administrative Tools > Local Security Policy.

Step 2

Navigate to Security Settings > Local Policies > Security Options.

Step 3

Choose Network Security: Minimum session security for NTLM SSP based (including secure RPC) servers.

Step 4

Verify that the Require NTLMv2 session security check box is unchecked.

Step 5

If the Require NTLMv2 session security check box is checked, complete the following steps:

  1. Uncheck the check box Require NTLMv2 session security.

  2. Click OK.

Step 6

To apply the new security settings reboot the Windows domain controller and server(s) running Exchange.

Note

 

The reboot is only required for servers on which a security policy configuration change was performed.


Set Exchange Impersonation Permissions for Specific Users or Groups for Exchange 2016 or 2019

Complete the following procedure using the Microsoft Exchange Management Shell (EMS) to set the Exchange impersonation permissions for specific users or a group of users.

These are the commands and settings for Exchange Server 2016 or 2019.

Procedure


Step 1

Create the account in Active Directory.

Step 2

Open the EMS for command line entry.

Step 3

Run the New-ManagementRoleAssignment command in the EMS to grant a specified existing domain service account (for example, Ex2016) the permission to impersonate other user accounts:

Syntax

New-ManagementRoleAssignment -Name:_suImpersonateRoleAsg -Role:ApplicationImpersonation -User:user@domain

Example

New-ManagementRoleAssignment -Name:_suImpersonateRoleAsg -Role:ApplicationImpersonation -User:Ex2016@contoso.com

Step 4

Run this New-ManagementRoleAssignment command to define the scope to which the impersonation permissions apply. In this example, the Ex2016account is granted the permission to impersonate all accounts on a specified Exchange Server.

Syntax

New-ManagementScope -Name:_suImpersonateScope -ServerList:server_name

Example

New-ManagementScope -Name:_suImpersonateScope -ServerList:nw066b-227

Step 5

Run the New-ThrottlingPolicy command to create a new Throttling Policy with the recommended values defined in the below table:

Syntax

New-ThrottlingPolicy -Name:Policy_Name -EwsMaxConcurrency:100 -EwsMaxSubscriptions:NULL -EwsCutoffBalance 3000000 -EwsMaxBurst 300000 –EwsRechargeRate 900000

Example

New-ThrottlingPolicy –Name IMP_ThrottlingPolicy -EwsMaxConcurrency 100 -EwsMaxSubscriptions unlimited –EwsCutoffBalance 3000000 -EwsMaxBurst 300000 –EwsRechargeRate 900000

Table 2. Recommended Throttle Policy Settings on Exchange Server 2016 or 2019

Parameter1

Recommended Configuration Value — Exchange Server 2016 and 2019

EwsCutoffBalance

3000000

EwsMaxBurst

300000

EwsMaxConcurrency

100

EwsMaxSubscriptions

Unlimited

EwsRechargeRate

900000

1 These are the only EWS parameters that can be changed in Exchange Server 2016 or 2019.

Note

 

Only available with supported Exchange SP1.

Step 6

Run the Set-ThrottlingPolicyAssociation command to associate the new Throttling Policy with the service account used in Step 2.

Syntax

Set-ThrottlingPolicyAssociation -Identity Username -ThrottlingPolicy Policy_Name

Example

Set-ThrottlingPolicyAssociation -Identity ex2016 -ThrottlingPolicy IMP_ThrottlingPolicy


What to do next

Verify Permissions on the Microsoft Exchange 2016 or 2019 Accounts

Verify Permissions on the Microsoft Exchange 2016 or 2019 Accounts

After you have assigned the permissions to the Exchange 2016 or 2019 account, you must verify that the permissions propagate to mailbox level and that a specified user can access the mailbox and impersonate the account of another user. It takes some time for the permissions to propagate to mailboxes.

Procedure


Step 1

On the Active Directory Server, verify that the Impersonation account exists.

Step 2

Open the Exchange Management Shell (EMS) for command line entry.

Step 3

On the Exchange Server verify that the service account has been granted the required Impersonation permissions:

  1. Run this command in the EMS:

    Get-ManagementRoleAssignment -Role ApplicationImpersonation

  2. Ensure that the command output indicates role assignments with the Role ApplicationImpersonation for the specified account as follows:

    Example Command Output

    Name - - - -

    Role - - -

    Role AssigneeName-

    Role AssigneeType-

    Assignment Method- - -

    Effective UserName

    _suImpersonate RoleAs

    Application Impersonation

    ex2016

    User

    Direct

    ex2016

Step 4

Verify that the management scope that applies to the service account is correct:

  1. Run this command in the EMS:

    Get-ManagementScope _suImpersonateScope

  2. Ensure that the command output returns the impersonation account name as follows:

    Example Command Output

    Name - - -

    Scope RestrictionType

    Exclusive

    Recipient Root - -

    Recipient Filter -

    Server Filter- - -

    _suImpersonate Scope

    ServerScope

    False

    User

    Direct

    Distinguished Name

Step 5

Verify that the ThrottlingPolicy parameters match what is defined in the below table by running this command in the EMS.

Get-ThrottlingPolicy -Identity IMP_ThrottlingPolicy | Format-List | findstr ^Ews

Table 3. Recommended Throttle Policy Settings on Exchange Server 2016 or 2019

Parameter1

Recommended Configuration Value — Exchange Server 2016 and 2019

EwsCutoffBalance

3000000

EwsMaxBurst

300000

EwsMaxConcurrency

100

EwsMaxSubscriptions

Unlimited

EwsRechargeRate

900000

1 These are the only EWS parameters that can be changed in Exchange Server 2016 or 2019.

Step 6

Verify that they ThrottlingPolicy has been associated with the Exchange Account.

Get-ThrottlingPolicyAssociation -Identity ex2016


Enable Authentication on Exchange 2016 or 2019 Running Windows Server 2016

Procedure


Step 1

From Administrative Tools, open Internet Information Services and choose the server.

Step 2

Choose Web Sites.

Step 3

Choose Default Web Site.

Step 4

Choose EWS.

Step 5

Under the IIS section, choose Authentication.

Step 6

Verify that the following Authentication methods are enabled:

  • Anonymous Authentication

  • Windows Authentication and/or Basic Authentication

Step 7

Use the Enable/Disable link in the Actions column to configure appropriately.


What to do next

Configure Certificates for Exchange Server Task Flow

SAN and Wildcard Certificate Support

The IM and Presence Service uses X.509 certificates for secure calendaring integration with Microsoft Exchange. The IM and Presence Service supports SAN and wildcard certificates, along with standard certificates.

SAN certificates allow multiple hostnames and IP addresses to be protected by a single certificate, by specifying a list of hostnames, IP addresses, or both in the X509v3 Subject Alternative Name field.

Wildcard certificates allow a domain and unlimited sub-domains to be represented by specifying an asterisk (*) in the domain name. Names may contain the wildcard character * which is considered to match any single domain name component. For example, *.a.com matches foo.a.com but not bar.foo.a.com.


Note


For SAN certificates, the protected host must be contained in the list of hostnames/IP addresses in the Subject Alternative Name field. When you configure the Presence Gateway, the Presence Gateway field must exactly match the protected host listed in the Subject Alternative Name field.

Wildcards can be placed in the Common Name (CN) field for standard certificates, and in the Subject Alternative Name field for SAN certificates.


Configure Certificates for Exchange Server Task Flow

Complete these tasks to configure certificates for a Microsoft Exchange deployment.

Procedure

  Command or Action Purpose

Step 1

Install the Certificate Authority (CA) on your version of Windows Server:

Although the Certificate Authority (CA) can run on the Exchange Server, we recommend that you use a different Windows Server as a CA to provide extended security for third-party certificate exchanges.

Step 2

Generate a CSR for your version of Windows Server:

You must generate a Certificate Signing Request (CSR) on the IIS Server for Exchange, which is subsequently signed by the CA Server.

Step 3

Submitting a CSR to the CA Server/Certificate Authority

We recommend that the default SSL certificate, generated for Exchange on IIS, should use the Fully Qualified Domain Name (FQDN) of the Exchange Server and be signed by a Certificate Authority that the IM and Presence Service trusts. This procedure allows the CA to sign the CSR from Exchange IIS.

Step 4

Downloading a Signed Certificate

Download a copy of the signed certificate.

Step 5

Upload the signed certificate to your version of Windows Server

This procedure takes the signed CSR and uploads it onto IIS.

Step 6

Downloading a Root Certificate

Download a root certificate from your CA server.

Step 7

Upload a Root Certificate to the IM and Presence Service Node

Upload the root certificate into the IM and Presence Service.

Installing a CA on Windows Server 2008

Procedure


Step 1

Choose Start > Administrative Tools > Server Manager.

Step 2

In the console tree, choose Roles.

Step 3

Choose Action > Add Roles.

Step 4

Complete the Add Roles wizard:

  1. In the Before You Begin window, ensure that you have completed all prerequisites listed and click Next.

  2. In the Select Server Roles window, check the check box for Active Directory Certificate Services and click Next.

  3. In the Introduction Window window, click Next.

  4. In the Select Role Services window, check these check boxes and click Next.

    • Certificate Authority
    • Certificate Authority Web Enrollment
    • Online Responder
  5. In the Specify Setup Type window, click Standalone.

  6. In the Specify CA Type window, click Root CA.

  7. In the Set Up Private Key window, click Create a new private key.

  8. In the Configure Cryptography for CA window, choose the default cryptographic service provider.

  9. In the Configure CA Name window, enter a common name to identify the CA.

  10. In the Set Validity Period window, set the validity period for the certificate generated for the CA.

    Note

     
    The CA issues valid certificates only up to the expiration date that you specify.
  11. In the Configure Certificate Database window, choose the default certificate database locations.

  12. In the Confirm Installation Selections window, click Install.

  13. In the Installation Results window, verify that the Installation Succeeded message displays for all components and click Close.

    Note

     
    The Active Directory Certificate Services is now listed as one of the roles on the Server Manager.

What to do next

Generating a CSR – Running Windows Server 2008

Generating a CSR – Running Windows Server 2008

You must generate a Certificate Signing Request (CSR) on the IIS Server for Exchange, which is subsequently signed by the CA Server.

Procedure


Step 1

From Administrative Tools, open the Internet Information Services (IIS) Manager window.

Step 2

Under Connections in the left pane of the IIS Manager, choose the Exchange Server.

Step 3

Double-click Server Certificates.

Step 4

Under Actions in the right pane of the IIS Manager, choose Create Certificate Request.

Step 5

Complete the Request Certificate wizard:

  1. In the Distinguished Name Properties window, enter the following information:

    • In the Common Name field, enter the Exchange Server hostname or IP address.
    • In the Organization field, enter your company name
    • In the Organizational Unit field, enter the organizational unit that your company belongs to.
  2. Enter your geographic information as follows and click Next.

    • City/locality
    • State/province
    • Country/region

    Note

     

    The IIS certificate Common Name that you enter is used to configure the Presence Gateway on the IM and Presence Service, and must be identical to the host (URI or IP address) you are trying to reach.

  3. In the Cryptographic Service Provider Properties window, accept the default Cryptographic service provider, choose 2048 for the bit length, and click Next.

  4. In the Certificate Request File Name window, enter the appropriate filename for the certificate request and click Next.

    Note

     

    Make sure that you save the CSR without any extension (.txt) and remember where you save it because you need to be able to find this CSR file later. Only use Notepad to open the file.

  5. In the Request File Summary window, confirm that the information is correct and click Next.

  6. In the Request Certificate Completion window, click Finish.


What to do next

Submitting a CSR to the CA Server/Certificate Authority

Submitting a CSR to the CA Server/Certificate Authority

We recommend that the default SSL certificate, generated for Exchange on IIS, should use the Fully Qualified Domain Name (FQDN) of the Exchange Server and be signed by a Certificate Authority that the IM and Presence Service trusts. This procedure allows the CA to sign the CSR from Exchange IIS. Perform the following procedure on your CA Server, and configure the FQDN of the Exchange Server in the:

  • Exchange certificate.
  • Presence Gateway field of the Exchange Presence Gateway in Cisco Unified CM IM and Presence Administration.

Before you begin

Generate a CSR on IIS of the Exchange Server.

Procedure


Step 1

Copy the certificate request file to your CA Server.

Step 2

Open one of the following URLs:

  • Windows 2003 or Windows 2008: http://locall_server/certserv

or

  • Windows 2003: http://127.0.0.1/certserv

  • Windows 2008: http://127.0.0.1/certsrv

Step 3

Choose Request a certificate.

Step 4

Choose advanced certificate request.

Step 5

Choose Submit a certificate request by using a base-64-encoded CMC or PKCS #10 file, or submit a renewal request by using a base-64-encoded PKCS #7 file.

Step 6

Using a text editor like Notepad, open the CSR that you generated.

Step 7

Copy all information from and including

-----BEGIN CERTIFICATE REQUEST

to and including

END CERTIFICATE REQUEST-----

Step 8

Paste the content of the CSR into the Certificate Request text box.

Step 9

(Optional) By default the Certificate Template drop-down list defaults to the Administrator template, which may or may not produce a valid signed certificate appropriate for server authentication. If you have an enterprise root CA, choose the Web Server certificate template from the Certificate Template drop-down list. The Web Server certificate template may not display, and therefore this step may not apply, if you have already modified your CA configuration.

Step 10

Click Submit.

Step 11

In the Administrative Tools window, choose Start > Administrative Tools > Certification > Authority > CA name > Pending Request to open the Certification Authority window. The Certificate Authority window displays the request you just submitted under Pending Requests.

Step 12

Right click on your request, and complete these actions:

  • Navigate to All Tasks.

  • Choose Issue.

Step 13

Choose Issued certificates and verify that your certificate has been issued.


What to do next

Downloading a Signed Certificate

Downloading a Signed Certificate

Before you begin

  • [Self-signed Certificates] Submit the Certificate signing request (CSR) to the CA server.

  • [Third-Party Certificates] Request the CSR from your Certificate Authority.

Procedure


Step 1

In Administrative Tools, open the Certification Authority. The Certificate Request that you issued displays in the Issued Requests area.

Step 2

Right click the request and choose Open.

Step 3

Choose the Details tab.

Step 4

Choose Copy to File.

Step 5

When the Certificate Export wizard displays, click Next.

Step 6

Complete the Certificate Export wizard:

  1. In the Export File Format window, choose Base-64 encoded X.509 and click Next.

  2. In the File to Export window, enter the location where you want to store the certificate, use cert.cer for the certificate name, and choose c:\cert.cer.

  3. In the Certificate Export Wizard Completion window, review the summary information, verify that the export was successful, then click Finish.

Step 7

Copy or FTP the cert.cer to the computer that you use to administer the IM and Presence Service.


What to do next

Upload of Signed Certificate onto Exchange IIS

Upload a signed certificate for your server type:

Uploading a Signed Certificate – Running Windows 2008

This procedure takes the signed CSR and uploads it onto IIS. To upload the signed certificate, perform the following step on the computer that you use to administer the IM and Presence Service.

Before you begin

[Self-signed Certificates] Download the signed certificate.

[Third-party Certificates] Your Certificate Authority provides the signed certificate.

Procedure


Step 1

From Administrative Tools, open the Internet Information Services (IIS) Manager window.

Step 2

Under Connections in the left pane of the IIS Manager, choose the Exchange Server.

Step 3

Double-click Server Certificates.

Step 4

Under Actions in the right pane of the IIS Manager, choose Complete Certificate Request.

Step 5

In the Specify Certificate Authority Response window, complete these actions:

  1. To locate your certificate, choose the ellipsis [...].

  2. Navigate to the correct path and filename.

  3. Enter a user-friendly name for your certificate.

  4. Click Ok. The certificate that you completed displays in the certificate list.

Step 6

In the Internet Information Services window, complete the following steps to bind the certificate:

  1. Choose Default Web Site.

  2. Under Actions in the right pane of the IIS Manager, choose Bindings.

Step 7

Complete the following steps in the Site Bindings window:

  1. Choose https.

  2. Choose Edit.

Step 8

In the Edit Site Binding window, complete the following steps :

  1. Choose the certificate that you just created from the SSL certificate drop-down list. The name that you applied to the certificate displays.

  2. Click Ok.


What to do next

Downloading a Root Certificate

Downloading a Root Certificate

Before you begin

Upload the Signed Certificate onto Exchange IIS.

Procedure


Step 1

Log in to your CA Server user interface and open a web browser.

Step 2

Open the URL specific to your Windows platform type:

  1. Windows Server 2008 – https://127.0.0.1/certsrv

Step 3

Choose Download a CA certificate, certificate chain, or CRL.

Step 4

For the Encoding Method, choose Base 64.

Step 5

Click Download CA Certificate.

Step 6

Save the certificate, certnew.cer, to the local disk.


Tip

If you do not know the Subject Common Name (CN) of the root certificate, you can use an external certificate management tool to find this information. On a Windows operating system, right-click the certificate file with a .cer extension and open the certificate properties.

What to do next

Upload a Root Certificate to the IM and Presence Service Node

Upload a Root Certificate to the IM and Presence Service Node

Before you begin

  • [Self-signed Certificates] Download the root certificate.
  • [Third-party Certificates] Request the root certificate from your Certificate Authority. If you have a third-party CA-signed Exchange server certificate, note that you must upload all CA certificates in the certificate chain to the IM and Presence Service as a CiscoUnified Presence Trust certificate (cup-trust).

Procedure


Step 1

Use the Certificate Import Tool in Cisco Unified CM IM and Presence Administration to upload the certificate:

Upload the certificate via:

Actions

Certificate Import Tool in Cisco Unified CM IM and Presence Administration.

The Certificate Import tool simplifies the process of installing trust certificates on the IM and Presence Service and is the primary method for certificate exchange. The tool allows you to specify the host and port of the Exchange server and attempts to download the certificate chain from the server. Once approved, the tool automatically installs missing certificates.

Note

 

This procedure describes one way to access and configure the Certificate Import Tool in Cisco Unified CM IM and Presence Administration. You can also view a customized version of the Certificate Import Tool in Cisco Unified Presence Administration when you configure the Exchange Presence Gateway for a specific type of calendaring integration (Log in to Cisco Unified CM IM and Presence Administration and choose Presence > Gateways).

  1. Log in to the Cisco Unified CM IM and Presence Administration user interface.
  2. Choose System > Security > Certificate Import Tool.

  3. Choose IM and Presence(IM/P) Trust as the Certificate Trust Store where you want to install the certificates. This stores the Presence Engine trust certificates required for Exchange integration.

  4. Enter one of these values to connect with the Exchange Server:

    • IP address

    • Hostname

    • FQDN

    The value that you enter in this Peer Server field must exactly match the IP address, hostname or FQDN of the Exchange Server.

  5. Enter the port that is used to communicate with the Exchange Server. This value must match the available port on the Exchange Server.

  6. Click Submit. After the tool finishes, it reports these states for each test:

    • Peer Server Reachability Status — indicates whether or not the IM and Presence Service can reach (ping) the Exchange Server. See Troubleshooting Exchange Server Connection Status.

    • SSL Connection/Certificate Verification Status — indicates whether or not the Certificate Import Tool succeeded in downloading certificates from the specified peer server and whether or not a secure connection has been established between the IM and Presence Service and the remote server. See Troubleshooting SSL Connection Certificate Status.

Step 2

If the Certificate Import Tool indicates that certificates are missing (typically the CA certificate is missing on Microsoft servers), manually upload the CA certificate(s) using the Cisco Unified OS Admin Certificate Management window.

Upload the certificate via:

Actions

Cisco Unified IM and Presence Operating System Administration

If the Exchange Server does not provide the CA certificates during the SSL/TLS handshake, you cannot use the Certificate Import Tool to import those certificates. In this case, you must manually import the missing certificates using the Certificate Management tool in (Log in to Cisco Unified IM and Presence Operating System Administration. Choose Security > Certificate Management).

  1. Copy or FTP the certnew.cer certificate file to the computer that you use to administer your IM and Presence Service node.

  2. Log in to the Cisco Unified IM and Presence Operating System Administration user interface.
  3. Choose Security > Certificate Management.

  4. In the Certificate List window, choose Upload Certificate/Certificate Chain.

  5. Complete these actions when the Upload Certificate/Certificate Chain dialog box opens:

    • From the Certificate Name drop-down list, choose cup-trust.

    • Enter the root certificate name without any extension.

  6. Click Browse and choose certnew.cer.

  7. Click Upload File.

Step 3

Return to the Certificate Import Tool (Step 1) and verify that all status tests succeed.

Step 4

Restart the CiscoPresence Engine and SIP Proxy service after you upload all Exchange trust certificates. Log in to the Cisco Unified IM and Presence Serviceability user interface. Choose Tools > Control Center - Feature Services.


Tips

The IM and Presence Service allows you to upload Exchange Server trust certificates with or without a Subject Common Name (CN).

What to do next

IM and Presence Calendar Integration Task Flow