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Adding SSL to Outlook Web Exchange

(SSL support is only available in OctaGate Switch Enterprise Edition)

OctaGate Switch as an SSL Frontend for Outlook Web Exchange

OctaGate Switch has successfully been used to add SSL to Outlook Web Exchange and it's very easy to do. Here we present a how-to on how to add SSL to your OWA 2000 mail.

If you need to provide secure internet access to your Outlook 2000 Web Access server, these are the steps you should follow.

We're currently working on a Wizard to take care of this.

Assumptions
  • You have already downloaded the latest OctaGate Switch.
  • Use the default certificate that are supplied with OctaGate Switch. This will still protect the connection, but you should probably make or purchase your own certificate
  • OctaGate Switch is running on 192.168.12.2 - this is the DMZ (adjust according to your actual settings)
  • Outlook Web Access 2000 is running on 192.168.1.2 - this is on your LAN (adjust according to your actual settings)
  • The FQDN is mymail.dyndns.org (FQDN = fully qualified domain name)

IMPORTANT NOTE:
You must set IIS on your OWA 2000 Server to use basic authentication only!!!

Follow these steps
  • Install OctaGate Switch
  • Open up a port 443 between your external firewall and OctaGate Switch. This effectively places the OctaGate Switch server on the DMZ.
  • Open up port 80 between OctaGate Switch server and Outlook Web Access 2000 Machine in your firewall.
  • Login to OctaGate Switch Administration Web and select Domains
  • Create a new domain, here are the essential settings you must update;

    Setting Value
    Domain Name FQDN (= mail.Domain-A.com in this example )
    Target Address 192.168.1.2 ( The Outlook Web Access server )
    Listen on port Tick the SSL box
    Outport Leave as port 80

    This is what it should look like once you're done;

  • Virtual Paths
    You don't need to add virtual paths if you don't want to change their behavior from the default domain behavior. If you set the "target address" of the domain to the OWA server, then that will be applied to all incoming requests.

    If you have 10 different OWA servers that you want to publish in different virtual paths, then you must create a virtual path for each and make sure it points to the right OWA server.
     
  • Make Outlook Web Access communicate with HTTPS headers
    To make Outlook Web Accress use "https" in it's urls, instead of "http", you need to add a custom header to tell it to do just that.

    Click "Headers" under the "Domains" menu, in the section "Add to/replace request header", add the following
    header;
       
    "Front-End-HTTPS: on"

    This is what it should look like once you're done;

  • Test it!
    Open a browser and type "https://mail.Domain-A.com/Exchange".
    You must make sure that "mail.Domain-A.com" resolves to the OctaGate Switch machine, otherwise it won't work.
    You should be prompted to accept the certificate. Enter your username and password.
    You should now see your inbox.
Troubleshooting

Here are a couple of troubleshooting tips. If these don't resolve any issues you're having, don't hesitate to contact our support team here.

"Loading" issue

If you see the left hand frame and the right hand frame just has a message that says "Loading" then there is a problem with WebDAV.

To resolve this, you can hide the browser type from Outlook Web Access by adding a custom header;
Click "Headers" under the "Domains" menu, in the section "Add to/replace request header", add the following header;

"User-Agent: none"

404 Error

If you get an 404 error, make sure that it works without SSL;

Uncheck the SSL box, remove "Front-End-HTTPS header". The try to access http://mail.Domain-A.com/Exchange directly. Note that that is "http", not "https".

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