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Monday, July 22, 2024

How to Configure/Troubleshoot Exchange 2013 Outlook Anywhere with Outlook 2013

Lets see how to configure Outlook anywhere for Exchange 2013

I have two servers load balanced Cloud1 and Cloud2 .

Open EAC – > Servers –>Servers –>Open the server properties –> Choose Outlook Anywhere

Specify internal hostname and External hostname as the same

Choose negotiate

Keep SSL offloading ON,  so that internal client have free traffic.

Do the same setting on both  the Exchange 2013 servers.


Now if you have a wild card certificate make sure you set this.

Set-OutlookProvider EXPR -CertPrincipalName:"msstd:*.domain.com"

Now to check everything is good.

To Test – 

Note (On-Premises) : Make sure you CNAME record is configured for autodiscover to work – Autodiscover.domain.com CNAME to Mail.domain.com

Login to


Run Outlook Anywhere (RPC over HTTP)


Multi-Tenant Scenario –

In a Multi tenant scenario – Make sure you got the srv record created . so that you need not to have more entries on the SAN Cert.

Lets say



is hosted on Cloud.com

You got configure a SRV record in Domain1.com and Point to Cloud.com , So that Outlook auto discover will contact Cloud.com Autodiscover and Outlook will work without any Certificate Errors

and you need not to buy Cert for Every domain you host on the cloud.

For Example a SRV record should look like :



By Using SRV record method


Recommended  Using Autodiscover Service for Outlook Configuration . As the Servername will be ExchangeGuid@ mailbox@domain.com

Make Sure Outlook is Updated using Windows Update

So that Outlook will support exchange 2013

Exchange 2013 support the following minimum versions of Microsoft Outlook and Microsoft Entourage for Mac:

  • Outlook 2013 (15.0.4420.1017)
  • Outlook 2010 Service Pack 1 with the Outlook 2010 November 2012 update (14.0.6126.5000).
  • Outlook 2007 Service Pack 3 with the Outlook 2007 November 2012 update (12.0.6665.5000).
  • Entourage 2008 for Mac, Web Services Edition
  • Outlook for Mac 2011


Satheshwaran Manoharan
Satheshwaran Manoharanhttps://www.azure365pro.com
Award-winning Technology Leader with a wealth of experience running large teams and diversified industry exposure in cloud computing. From shipping lines to rolling stocks.In-depth expertise in driving cloud adoption strategies and modernizing systems to cloud native. Specialized in Microsoft Cloud, DevOps, and Microsoft 365 Stack and conducted numerous successful projects worldwide. Also, Acting as a Technical Advisor for various start-ups.

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  1. Hi

    I currently have a DAG setup with 3 member servers and the internal host (servername.domain.local) on each server is the server name. Outlook, active sync and owa are working, however I want to setup outlook anywhere. My external host name is different from the internal host, I also have a wildcard certificate. Will outlook anywhere still work? Can I just import the certificate and enter the external url. Will this affect the internal certificates?

    • I Prefer Rename the internal URLs and External URLs to be Same. if its a single site.
      Makes life Simple. and .Local is not Supported anymore. on External Certs.


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