Microsoft Exchange/Office365

Setup Outlook Anywhere: A Quick Guide

remote email access

Explore the seamless world of email access with our quick guide on how to setup Outlook Anywhere. Discover the simple steps to keep yourself connected, no matter where you are.

Here are the vital areas that need to be considered.

  1. Autodiscover
  2. Outlook Anywhere
  3. SSL certificate is in line with your domain name, and this should be installed on the IIS.
  4. RPC over HTTP needs to be added as a feature in your server using the server manager etc., depending on the Windows server you are using
  5. After configuring all these steps, ensure to text using for possible causes of errors to find a fix. Note: For a seamless experience with Outlook, ensure you’ve correctly set up Outlook Anywhere. Moreover, Access this site through Exchange or use the Remote Connectivity Analyzer in the console tree under “Tools” in the Toolbox pane.
    Nonetheless, This tool is vital as it will analyze where all the errors are hindering Outlook anywhere connectivity.

Described Steps to achieve setup Outlook Anywhere the above-mentioned requirements

To achieve seamless email access and remote connectivity, follow these steps: Setup Outlook Anywhere, and you’ll quickly meet the above-mentioned requirements. It’s a straightforward process that ensures you stay connected effortlessly.

Step 1 Auto discover. Check on your Webserver (IIS) on exchange server.
To get here, click on the server manager and expand the roles, select webserver and then Internet Information Service (IIS), and ensure you have your Autodiscover and RPC etc. available.

Now click on the DNS manager,
Expand the forward lookup zone,
Create an A record for Autodiscover in your DNS to resolve
internal and external IP Addresses.
Note: these are the IP address assigned to the internal and external URLs (i.e. the IP in which these URL can be reached externally and internally).

Step 2 Enabling Outlook anywhere

Note: You should already have your internal and external virtual directory URL (FQDN) in place for users to access Outlook/OWA internally and externally. However, Most of the time, they are the same but can also be different.

This can be done under the server configuration,
select client access
and on the Action pane, select Configure External Client and
then click on Enable Outlook Anywhere.
Now click on Properties to select the Authentication type and hostname.

See the link and steps below for a better understanding.

You would also enable the Client Access server for Outlook Anywhere to work. The external hostname must be specified using the Enable Outlook Anywhere wizard or the Power Shell. See link       

Configuring the External hostname

  1. In the console tree,
  2. Navigate to Server Configuration and click on Client Access.
  3. On the action pane, click Properties.
  4. On the Exchange (Default Web Site) Properties page, click the Outlook Anywhere tab.
  5. In the text box under External hostname, enter the external host name for this site.

Note: Now select the authentication method you want to use, which can be done via PowerShell or EMC. See link

In my scenario, we opted for a different approach: Setup Outlook Anywhere using the NTLM authentication method. This choice offered distinct advantages for our email access.

Step 4. Ensure secure access with SSL Offloading setup Outlook Anywhere. Nonetheless, this crucial configuration enhances connection security, allowing seamless communication for your remote email needs.

This is usually done the very first time you enable Outlook anywhere wizard. However, enable SSL offloading by selecting the check box next to Allow secure channel (SSL) offloading and see the link for further information if needed

Step 4. Note: Without SSL, there is no way we can make use of Outlook anywhere except we have rpc virtual directory configured to use Secure Sockets Layer (SSL).

See link on the configuration steps

Note: In my case, I had all these configured before, but to fix some basic issues not enabled, which might help you.

Step 5: Create a certificate request, create a certificate, and install the certificate by completing the certificate request. See the following link

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