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Secure Outlook Web Access with (free) SSL

Justin Fielding at Tech Republic reviews how to secure Outlook Web Access using an SSL certificate from a free Certificate Authority.

I have recently spent some time building a small Active Directory / Exchange 2003 environment in my home lab. One thing that bothered me was the lack of encryption while using Outlook Web Access (OWA) in its default state. Over the next couple of weeks I’m going to run through the steps needed to secure OWA from requesting a certificate to installing CA trusts on the client side.

Digital certificates

In order to secure OWA, the first thing we need is a valid certificate. There are three ways you can get this:

  1. Buy a certificate from Verisign, Thawte, etc.
  2. Create your own CA and Certificates.
  3. Obtain a free certificate from StartCom!

If cost is not a consideration, and the services you want to secure are going to be used by the public at large, then buying a domain root certificate ( e.g *.mydomain.com) is probably the best solution. The certificate authority will already be recognised by 99.9% of operating systems, browsers, and applications requiring no additional configuration on the client’s part.

He goes over the process in two articles.

The process of obtaining and installing a certificate is fairly straightforward:

  • Generate a new certificate request
  • Export certificate request
  • Request certificate from CA (StartCom)
  • Import generated certificate
  • Add CA trust

Secure Outlook Web Access with (free) SSL: Part 1 - [TechRepublic]
Secure Outlook Web Access with (free) SSL: Part 2 - [TechRepublic]

Originally posted on Sat Jul 28, 2007

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