Configuring Outlook (Exchange 2007/2011) to work over an SSH tunnel


I never liked using VPN for accessing my corporate mail because it routes all my personal traffic also through the corp pipeline (say youtube, facebook,torrents etc).  I was a happy Thunderbird user, but the recent policy change dumping all IMAP access, really pushed me to the corner to use an Outlook Client now.. So I wanted it to work over an SSH tunnel just like my other apps (firefox, terminal etc).

Here is what I did setting up RPC over HTTPS to make it all work:

  1. It needs the ports 80 and 443 of your mail server (which might well be sitting behind a firewall) to be available to the localhost;
  2. So I forwarded my local ports 9980 and 9443 for this purpose;
  3. Open Outlook.. In ‘Tools->Accounts->Advanced”.. enter the server name as “https://localhost:9980/ews/exchange.asmx” and the port as 9443;   pl tick “override default port” to enter the port..
  4. Enable logging just in case if something goes wrong.. “Window->Error Log->Turn on Logging….”

whoosh.. and you just have to click ‘sync’.. 🙂  Mail and Calendar are working seamlessly.. To check further if anything else is broken and then to fix it..

Extending it:

  1. So I have a script that always forwards the above two ports, whether I am within the corp LAN or outside of it.. In that way, I never need to change the Outlook settings and it should work seamlessly.
  2. What would change in this setup when we move to Outlook 2011? I am not sure, yet to figure it out..

hope this helps you get rid of the VPN… thanks for reading.

/balu/

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