This article will guide you through the necessary steps to install and configure Outlook Anywhere (RPC over HTTP) on Microsoft Exchange 2010 and Microsoft Exchange 2007.
Most screenshots are taken using Windows Server 2008 R2, Exchange 2010, and Outlook 2007. Earlier versions of the software may have slightly different menu options.
Installation Steps
On The Exchange Server
- Install RPC over HTTP on the Exchange Server
- Enable & Configure Outlook Anywhere
On the Outlook Client
- Configure Outlook Settings
- Start Outlook and Verify
Exchange Server Steps
1. Install RPC over HTTP
Start Windows Server Manager, and go to Features ⇒ Add Feature ⇒ RPC over HTTP Proxy:

2. Enable & Configure Outlook Anywhere
Launch the Exchange Management Console, then navigate to Server Configuration ⇒ Client Access
Right-click on the server in the right-hand window and choose Enable Outlook Anywhere
The External Host Name should be the external FQDN (DNS) name for the server, eg mail.mycompany.com
Choose NTLM authentication:

Monitor the Windows Application Log in Event Viewer and wait for the configuration to be updated (this can take up to 15 minutes):

On the Outlook Client
3. Configure Outlook on the Client
Start Outlook and choose Manually configure server settings:

Choose Microsoft Exchange as the server type:

Use the internal DNS name of the Exchange server (eg exchange.mycompany.local), and type in the user's mailbox name. I recommend that you also tick Use Cached Exchange Mode as this will considerably improve the performance of Outlook on the client computer. Then click on More Settings...

On the Security tab, tick Encrypt data between Microsoft Office Outlook and Microsoft Exchange, and set the Logon network security to Negotiate Authentication:

On the Connection tab, select Connect using my Local Area Network (LAN), tick the box underneath Outlook Anywhere that says Connect to Microsoft Exchange using HTTP, and then click on Exchange Proxy Settings:

The URL of the proxy server for Exchange is the external FQDN (DNS) name of your Exchange server, and is probably the same name as your Exchange OWA (eg mail.mycompany.com, or webmail.mycompany.com):

Tick Connect using SSL only, tick Only connect to proxy servers that have this principle name in their certificate, and then type msstd: followed by the Subject name of the SSL certificate installed on your Exchange server. This may be the same as your WebMail address (eg webmail.mycompany.com) or it may be something different. If in doubt then have a look at the certificate installed on your Exchange server. You can do this from within IIS on the Windows server, or by browsing to your Exchange WebMail in Internet Explorer and viewing the certificate. On the Details tab look for the Subject field:

Tick On fast networks, connect using HTTP first..., and also On slow networks...
Set the Proxy authentication settings to NTLM Authentication - this must match what was set on the Exchange server in step 2:

Click OK, OK, Next, then Finish
4. Start Outlook
Now when you start Outlook you should be prompted to login to your Exchange server. You need to include the NetBIOS name of your domain with the username (eg MYCOMPANY), and you can tick the box to Remember my password so that the user doesn't see this again (this works with Outlook 2010, it doesn't always work with Exchange 2007):

Outlook should now start, and it should load the User's mailbox. Since we're using Cached Exchange Mode, it will take some time to download the user's mailbox on the first connection. You may therefore prefer to do this on the LAN before your user connects remotely for the first time!

That's it, you're done!