Can't access Outlook Web App outside of the network
<p>Hello, we are using a Microsoft Exchange 2013 server on Windows Server 2012 R2 with IIS.</p>
<p>After the Exchange was completely installed, it installed itself on IIS. I haven't made that many changes to it. I changed the binding IP from the 127.0.0.1 to the Exchange server IP but that's all I can recall for the changes that I kept. There is no problem with accessing it through domain computers and computers not on the domain but are on our network. However, it's when we try to access it outside the network that we get issues.</p>
<p>In Google Chrome outside the network, we are getting to the part where Google tells you the certificate is unsafe and then allows us to proceed if we want to. From there, we get an HTTP 404 error.&nbsp;</p>
March 9th, 2015 3:14pm

Exchange configures IIS as part of installation, not afterward.

It appears the client machine you're using doesn't trust the certificate that's being presented to it.  It sounds from your description that you didn't obtain a third-party certificate and you're using the default self-signed certificate.  Machines will need to trust that certificate to avoid a certificate error.

If you're getting a 404 using OWA, it's not likely related to the certificate.  OWA will work after you accept the certificate warning.  So the problem is probably related to your client not being able to reach the Exchange server through your firewall, NAT, reverse proxy, or whatever else is in the way.

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March 9th, 2015 7:53pm

Exchange configures IIS as part of installation, not afterward.

It appears the client machine you're using doesn't trust the certificate that's being presented to it.  It sounds from your description that you didn't obtain a third-party certificate and you're using the default self-signed certificate.  Machines will need to trust that certificate to avoid a certificate error.

If you're getting a 404 using OWA, it's not likely related to the certificate.  OWA will work after you accept the certificate warning.  So the problem is probably related to your client not being able to reach the Exchange server through your firewall, NAT, reverse proxy, or whatever else is in th

March 10th, 2015 9:21am

Again, the 404 is probably separate from the certificate.  If it works differently from outside than inside, you need to investigate what's different, and that's usually firewall, reverse proxy, NAT and the like.
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March 10th, 2015 3:50pm

Again, the 404 is probably separate from the certificate.  If it works differently from outside than inside, you need to investigate what's different, and that's usually firewall, reverse proxy, NAT and
March 10th, 2015 4:11pm

So that server works from inside your network?  Again, if it works from inside your network and from outside it doesn't, there has to be something in between that's causing problems.  You might want to look at the IIS logs to see if anything shows up there when you connect from outside and from inside.
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March 11th, 2015 12:15am

So that server works from inside your network?  Again, if it works from inside your network and from outside it doesn't, there has to be something in between that's causing problems.  You might want to look at the IIS logs to see if anything shows up there when you connect from outside and fr
March 11th, 2015 9:53am

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