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Outlook Web Access no longer working under SSL. Or at all in fact.

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Join Date: Feb 2009
Posts: 43
#1: Aug 27 '09
Hi all;
This is driving me up the wall! A few months ago the Remote Web Workplace failed to work on a pretty much fresh install of SBS 2003. I tried everything in the Microsoft rulebook to get it working but instead OWA started playing up. Forms-based authentication stopped working, then it started coming up with Page Not Found errors, but -only- if SSL was turned on at the server end. If I turn SSL off then forms-based authentication starts working again. Either way, all the mailboxes are now empty after login. Below is a list of the problems in a more concise format, if anyone has any insights into it then that would help massively. I'm not even 100% sure how OWA actually hangs together (how it connects from IIS to Active Directory to Exchange, for example) so any sources of information would be great. Here we go:

1. OWA stopped working during an attempt to get the Remote Web Workplace running. RWW never worked out-of-the-box.
2. All attempts to get OWA working (as per the Microsoft KB) either didn't work or made it worse.
3. I tried reinstalling Exchange and IIS together (as per MS KB articles). This broke the Exchange transport system but didn't fix the problem.
4. Tried reinstating the default directories. This didn't work, and also broke the SSL certificate. https://vpn.me.com/exchange now gives 404 errors.
5. Disabled SSL on Default Web Page in IIS. http://vpn.me.com/exchange (no SSL) now logs in but all the mailboxes are empty. At this point I gave up. Two months later:
6. http://vpn.me.com/exchange brings up the login page but now none of the logins register.

It's a good job there's only four of us in the company, otherwise I'd be in real trouble! Anyone have any ideas on how to fix this, or anywhere I can go to make a start on piecing the system back together block by block?

Thanks folks!
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