Little Annoyances : Using Outlook over the Internet without VPN

Vivek Venugopalan

Revision History

Table of Contents

Introduction
Minimum requirements to use this feature
Configuring Outlook
Troubleshooting
References

Abstract

This article outlines how to use Microsoft Outlook without VPN to download E-mail while on the road.

Introduction

Microsoft Outlook is a very popular corporate email client even though the general population typically has mixed opinions about it. Its close integration between communication and scheduling through calendars and notes gives it that edge in the corporate market. A significant part of the success should be attributed to the (in)famous outlook client that helps in this integration. To achieve this, outlook client has traditionally employed a proprietary protocol to the server to exchange information.

What that means for road warriors is to fire up VPN everytime you have to download email. I just hated that because our corporate VPN connection is a bit flaky and decides to drop the connection at the slightest hint of packet loss. Secondly the engineer in me didnt like using a chainsaw to perform a microsurgery.

Microsoft has over the years also figured out this problem. They have used RPC as the protocol to communicate between the server and client. If you leave all the technical jargon aside, bottomline, outlook can talk to the mail sever directly over the internet without a pesky VPN in the middle. This article will explain step by step how this can be achieved.

Minimum requirements to use this feature

Before you get too excited, there a few minimum requirements that have to be satisfied before you can relieve your outlook from the VPN shackles. They are

  1. Microsoft Windows XP Service Pack 1 (SP1) with Microsoft KB 331320 updates installed

  2. Your Exchange server administrator must have configured the server to permit connections via HTTP

if you dont satisfy the minimum criteria then you won't be able to use this feature of outlook.

Configuring Outlook

The following steps have to be followed to configure outlook to download mails from your mail server directly over the internet.

Selecting the E-mail account

Log into your outlook in online mode and select Tools->email accounts option.

You will be presented with the "E-mail accounts" dailog as shown below. Here you need to select "View or change existing e-mail accounts" option and click next.

When presented with a list of E-mail accounts to modify, select the account for which you want to enable HTTP-RPC and select Change as shown below.

Modifying your mail account

On the selected E-mail account, ensure that "Cached Exchange mode" has been turned on. This apparently has a significant performance influence on outlook if we use HTTP-RPC. I am not sure about the specifics but I suggest you play with it - "your mileage may vary"

Select "More Settings..." to popup another dialog box (below) where we configure the nuts and bolts of the communication between the client and server.

On the "Microsoft Exchange Server dialog (above) select the "Security" tab and select "Encrypt data between Microsoft office outlook and Microsoft Exchange Server".

Click on the "Connection" tab to see the settings below. The interesting settings are at the bottom "Exchange over the internet". Select the "Connect to my exchange mailbox using HTTP" option to enable the "Exchange proxy settings" button below it. Click on this button to configure the server settings.

[Note] Note

If the "Exchange over the internet" option is not available. A few things could be wrong - some of which we can try to tweak and some which we cannot do much about. Follow the Troubleshooting section to see what can be done - again - your mileage may vary.

Once you click on the "exchange proxy settings", the following dialog will popup.

This is where you should configure the HTTP-RPC settings. The settings for various items are.

  1. Connection Settings -URL : Specify the exchange server with which outlook will synchronize E-mail over HTTP-RPC. Typically this could be the same as your webmail server since it allows the usage of the same sever certificate for a secure (https) connection. But this need not be the case, do check your system admin group to get the right server name.

  2. Connect using SSL Only: Select this to ensure that Outlook does not send unencrypted data over the internet.

  3. Select "On slow network, connect using HTTP first, then connect using TCP" - the idea being that on the road you will have a slower network as compared to work. If you are unsure, then it is better to select both the options so that the system always uses HTTP-RPC first.

  4. Proxy Authentication Settings: Again this is going to depend on how your administrator has configured your exchange server. Typically basic authentication will work but if your exchange has been configured for NTLM authentication, that is the prefered way to go.

Once these changes are done, save the settings and restart outlook. The new settings should take over and you should start seeing E-mail flowing through without VPN.

Troubleshooting

This is a growing section. I will be adding more notes here as and when I hear more problems and solutions from you folks who are reading this article and trying various stuff on outlook. Please feel free to drop me a note on issues faced and some tips/tricks on how you managed to resolve them.

References

Google
Web www.sanchivi.com