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I have an Exchange 2007 server that went down after a power failure. It has OWA access via SSL both externally and internally. OWA is working fine from the internal notwork, however I am getting a timeout when I attempt to connect externally. I pulled up wireshark and noticed that the server actually redirects to SSL. For some reason the server is not listening on the SSL port, and this seems to be causing the timeout.

I normally do only development work, but I'm stuck with this since my sysadmin took off for the week and isn't answering my phone calls. As far as I know it shouldn't be a firewall issue. Aside from me not wanting to work on the damn thing, what should I look for?

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So OWA works on SSL internally? – Ben Pilbrow Dec 30 '10 at 16:46
Shame on your sysadmin for not working on his vacation. How dare he! – Jason Berg Dec 30 '10 at 16:46
I'm going to go out and say this, since you obviously have no desire to work on servers. Consider hiring a consultant or paying Microsoft $350 for the ticket. I know it's not answering your question, but it's going to be the least amount of work for you. – Jason Berg Dec 30 '10 at 16:48
@Jason haha well there's a couple of them. And one is supposed to answer during the week. How was I supposed to know sysadmins slept? @Ben OWA works fine internally. – krs1 Dec 30 '10 at 16:48
up vote 0 down vote accepted

Check the IIS bindings to make sure that the public and internal IPs are both bound to the same site. Also, try testing with the public IP, but while logged into the server. If that works then it's likely a firewall issue. If it doesn't work then you have something wrong on the server.

Since you mentioned it stopped working after a power failure, something that I've seen happen a few times is for admins to setup a new site that has identical bindings as another site. This will cause the new site to not start. Then they leave the site there rather than cleaning up. After a reboot, it's a race condition which site starts, and sometimes the wrong one will. So, check for another stopped site that may be the real site, and the one that started may be a troubleshooting or incorrect site.

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