How to use Outlook Anywhere in Exchange Server 2010


Microsoft Exchange Server is designed to work well with Microsoft Outlook. So how do you get Microsoft Office Outlook to work with Exchange Server? In previous articles and videos, I demonstrated how to connect to the Exchange Server using POP3 non-Outlook mail clients, like Windows Mail and Thunderbird, and we also connected to our mail with webmail, using Microsoft OWA, but what about Outlook? Since Exchange Server was designed to work with Outlook it should be straightforward right? Not necessarily, especially if you are a beginner like me. To be fair, Outlook should connect to your Exchange Server easily if your computer is on the domain. If you are already authenticated to the domain the ability to connect to your email user account should be automatic. What if you are not on the local network or domain? One solution is to first connect to the network using a VPN tunnel and then Outlook can easily connect to the Exchange server since it is: a) on the network; and b) on the domain. A more difficult scenario is to connect to your Exchange user mailbox, using Outlook, without a VPN tunnel, meaning you are not on the domain, and you are not on the local network. In order to do this, you will need to use Exchange Server 2010’s Outlook Anywhere feature.


 Outlook Anywhere

In order to connect to your 2010 Exchange Mail Server, with Microsoft Outlook, using the “Outlook Anywhere” feature, you will need the following things configured and available:

  • Autodiscover
  • Outlook Anywhere
  • Certificate of Authority (CA) or SSL Certificate – you will need to purchase an SSL certificate that matches your mail domain name and install it in your IIS Web Server
  • RPC over HTTP – you will need to add this feature using the Server Manager
  • Remote Connectivity Tester Tool – there is a link to this tool in the Toolbox in the Exchange Management Console
  • also:
  • DNS – you will need to create an “A Record” to point “autodiscover.<your domain name>” to your ip address
  • Firewall – your firewall router will need to have port 443(https) open and forwarding to your mail server since Outlook Anywhere requires an SSL certificate.

Video Tutorials on Configuring Outlook Anywhere

Outlook from within the Domain

A good initial test of Outlook is to see if you can connect to your mail account with Outlook from within the domain. To connect Outlook to your Exchange Server email account you will access the following Exchange features:

  • Autodiscover
  • Certificate of Authority (CA) or SSL Certificate – Exchange will allow you to connect using the local server generated certificate

In our tests Microsoft Outlook 2010 and 2007 worked perfectly. Here are the steps to connect Outlook to your email account from within the domain:

  1. First join your computer to the domain.
    Start menu > right click on “Computer” > click on “Properties” > click on “Advanced System Settings” (Windows 7) > the “Computer Name” tab > click “Change” >   click the “Domain” radio button and add your domain name > Click “Ok”
  2. Now you need to add your email account information in Outlook by either going straight to Outlook or going to the “control panel”, clicking on “Mail” and inputting your email account and password information.
  3. Now that you have successfully connected to Outlook from within the domain you can try configuring Outlook Anywhere to connect from outside of the domain.

Create a send connector to send outside mail


You have an Exchange email server that can send mail to and from mailboxes within your domain or organization, but can you send mail outside of the domain, for example: to a gmail or yahoo email account? The answers right now is no. By default in Microsoft Exchange Server 2007 or 2010 mail is restricted to within the domain only. In this assignment, you will configure a send connector on the Hub Transport Server in order to relay mail to outside of the domain.

In the following example mail is successfully sent outside of the domain because of the send connector which is created and because the domain name is publicly registered with a registrar and the DNS and MX records are successfully resolving to the mail server. In order for mail to be sent outside of the domain on your mail server you will need to have your domain name publicly registered and resolving. If the domain you configured with your mail server is only functioning locally on your own LAN then this lab is still valuable as a learning process for configuring send connectors and email clients.

Video Tutorials and Demonstration

This video is mostly a review of some of the working configurations on the 2010 Exchange Server

This video covers how to create a send connector on Exchange Server 2010 in order to send email outside of the domain

Install Server 2008 R2 and Exchange Server 2010

Installing Exchange Server 2010 Overview

Installing Microsoft Exchange Server can be a daunting task. There are some pre-installation decisions and preparations to be made. You will need to check to see if your version of Windows Server 2003 (32bit or 64bit), 2008, or 2008R2 is compatible with the version of Exchange Server (2007 or 2010) that you are planning to install. There are also a lot of options on how you can run your Exchange install, either using the GUI Setup Wizard, a command line install, or a scripted install.

By default Exchange Server 2007 and 2010 are 64 bit. Although you can install 2007 in 32bit for a non-production test environment. Here are my recommendations of what could work for you in the lab or at home:

  • Server 2008 R2 and Exchange Server 2010 (64 bit) – The newest architecture is recommended
  • Server 2008 and Exchange Server2007 (64 bit)
  • Server 2003 (64 bit) and Exchange Server 2007 (64bit)
  • Server 2003 (32 bit) and Exchange Server 2007 (32bit) – If you can only run 32 bit

Hardware Requirements

Exchange Server 2007/2010

How many servers will Exchange Server roles be installed on 1, 2, 3 or 4 separate servers?
64 bit architecture (Yes please)
2 Gig RAM (min)
Enough hard disc storage space to support your users. In order to achieve this you could use:
– a local hard drive or drives
– a SAN (storage area network) storage system
– a IP SCSI NAS (network-attached storage)

Pre-Installation Checklist

For an install of Exchange Server 2007/2010 to work you will need the following things installed or added to your Windows Server platform. (3, 4, and 5 below are installed by default when installing Server 2008 or using the Exchange setup wizard):

  1. Active Directory –  (add role)
  2. DNS – (add role)
  3. The server will need to be a Domain Controller (dcpromo) and Global Catalog Server
  4. .NET framework
  5. Microsoft Management Console (MMC)
  6. Windows Power Shell
  7. Microsoft IIS – (add role)
  8. WWW Publishing Services – (add role):
    You may need to specify many of the IIS services (like IIS 6.0 and XML 6.0) and make sure the WWW server is running
  9. Net.Tcp Port Sharing Service will need to be set to automatic (Go to Start > Run > services.msc > and look for Net.Tcp Port Sharing)

The Exchange Server 2007/2010 setup wizard makes the process a lot easier. The wizard will run through a checklist of items to make sure your system meets the necessary requirements. If your computer does not meet the requirements you will be prompted to search and install the necessary tools that the installation requires.

Exchange Server Mail Roles

When installing Exchange Server you need to decide which specific mail roles or servers you will need. There are five different servers within Exchange Server that you can install:

Mailbox Server
Client Access Server
Hub Transport Server
Unified Messaging Server
Edge Transport Server

In this class you will need to install the Mailbox, Client Access and Hub Transport servers. The Unified Messaging Server and Edge Transport Servers are typically installed on separate servers and are not needed for a small test purposes installation.

Video Tutorials

Install Active Directory, DNS and IIS and promote the server to a DC and GCS

Install Exchange Server 2010