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I've configured a fresh Exchange 2013 server on a 2012 box. It's all working correctly aside from that internal computers will not run the autodiscover wizard.

I have attempted multiple troubleshooting steps and none have been successful. It does autodiscover externally. Also the Microsoft Test Connectivity passes successfully (aside from the SSL identity, which is fine as I'm deploying the self-signed cert with a GPO.).

The error I'm receiving on the client is:

The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.

If I set the connection settings manually with HTTP etc. it does connect, however then there are still problems moving emails between folders. Plus, I cannot afford to go around every machine doing this manually.

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How did you setup your internal URLs and URI for autodiscover? What DNS names are you using internally? Did you create an autodiscover DNS record(s) to point to the internal Exchange 2013 server? After starting Outlook, right click the outlook icon in the taskbar tray while holding CTRL and choose "Test email autoconfiguration" and then press the "Test" button. What are the results?

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  • I've created the Forward Lookup Zone and pointed autodiscover.publicdomain.co.uk to the servers internal IP address. I also tried using SRV records? When I run the test, it all returns back as I would expect. Finds the autodiscover files etc. – GRitchie Sep 8 '15 at 8:13
  • How about your virtual directories? How is the InternalURL configured? Did you configure OutlookAnywhere correctly? I have found this article pretty helpful in configuring our own Exchange 2013 environment. This is actually a migration from exchange 2010 to 2013 article, but it still contains a lot of useful configuration information regarding Exchange 2013: exchangeserverpro.com/… Did you try to recreate an outlook profile from scratch? If you ping the internal server from the client do you get a reply from the internal ip? – Erik Sep 8 '15 at 8:45
  • I read online that I should set all the virtual-directory internal URLs to the same as the external. As of that, my Outlook Anywhere URL is mail.publicdomain.co.uk. I can ping the server internally. I've tried recreating the profile from scratch on multiple machines. – GRitchie Sep 8 '15 at 8:51
  • How about the outlook provider? What is the output if you run 'Get-OutlookProvider' in EMC ? – Erik Sep 8 '15 at 9:11
  • Shows NAME (EXCH, EXPR, WEB) then nothing listed next to 'server'. – GRitchie Sep 8 '15 at 9:36
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Couple of things for you to configure:

  1. Virtual Directories.

  2. Review your certificate and DNS configuration. You need to implement something called split DNS. You need to create and configure the external zone the is used in your external DNS for Exchange, inside your internal DNS server. You need to make sure that your certificate lists the internal name for the Exchange that you want to use. Since Autodiscover works properly externally, as you indicated, there's no need to deploy and configure certificate using GPO, once the proper configuration is used.

  3. As for the cert, make sure you're deploying a proper 3-rd party SAN or wildcard SSL.

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  • I'm using a self-signed cert (I know it's advised against, but it does still work). I've configured a forward lookup zone for the public domain (within my local AD/DC DNS). Pointing autodiscover.publicdomain.co.uk to the internal server's IP. I've also tried using SRV records for _autodiscover with _tcp. – GRitchie Sep 8 '15 at 8:17
  • Did you configure the virtual directories? – Vick Vega Sep 8 '15 at 18:49

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