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How to Configure Outlook Anywhere in Exchange Server 2010

Outlook Anywhere allows remote clients using Microsoft Office Outlook 2010, Outlook 2007 and Outlook 2003 to connect to Exchange 2010 server from outside the corporate network over the Internet. If you have already installed an SSL certificate and allowed your remote clients to use OWA (Outlook Web App), as we have demonstrated in our Screencast:
How to Install GoDaddy Multiple Domain (UCC) SSL Certificate in Exchange 2010
then configuring Outlook Anywhere is the next logical step. The advantages of this feature are:
– Users get full access to their mailboxes over virtually any network without the need of a VPN solution or additional firewall rules
– You can use the same URL that you use for Outlook Web App and Microsoft Exchange ActiveSync
– You can use the same SSL certificate implemented for Outlook Web App and Exchange ActiveSync
– Unauthenticated requests from Outlook cannot access Exchange Server

The SSL certificate which you are using on your Exchange 2010 Client Access server is one of the key factors which determine the configuration steps which you should follow.
Using a trusted Multiple Domain SSL certificate is the easiest (and recommended) scenario and we will start with it. As you will see in our demo, this allows fully automated client configuration of autodiscover capable remote clients – MS Outlook 2010 and Outlook 2007, based solely on the users e-mail address. MS Outlook 2003 clients require manual configuration. We demonstrate it (Step3), as it is a good idea to be able to perform a manual Outlook Anywhere configuration (even with autodiscover capable clients) as part of your troubleshooting techniques.
Your other SSL certificate options are:
-Generating and using a Self-Signed Multiple Domain Certificate
-Configuring a Microsoft CA and issuing a Multiple Domain Certificate, signed by it
-Using a trusted Single Domain SSL certificate and configuring an Autodiscover SRV record in your external DNS zone

All these scenarios require additional configuration steps – both from administrator’s and end user’s perspective. To keep things simple, we will cover these scenarios in separate Screencasts.
Choosing the authentication type for your Outlook Anywhere configuration is one of the important decisions which you will have to make and we discuss the pros and cons of the available options in step1. In addition, we focus our attention on a problem, specific to remote MS Outlook 2010 clients – the wizard suggests the e-mail address as a UPN (user principal name), and as you will see this might cause authentication issues based on your network configuration.
In our demo, we are using a Single Exchange Server 2010 SP1 installed on a Windows Server 2008 R2.

Click to play 1 video
Step 1 We start by installing the RPC over HTTP Proxy feature. Then, we enable Outlook Anywhere – special attention is paid when choosing the suitable authentication method.

Click to play 2 video
Step 2 Next, we configure autodiscover record in the external DNS server for our domain and perform Outlook Autodiscover and Outlook Anywhere Connectivity tests with Microsoft Exchange Server Remote Connectivity Analyzer.

Click to play 3 video
Step 3 In this step, we demonstrate the configuration of Microsoft Office Outlook 2010, Outlook 2007 and Outlook 2003 clients.

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