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I'm trying to configure an Outlook client to use RPC over HTTP so that my client can read his mail without connecting to the VPN. The mailserver is an SBS2011 server and Outlook Anywhere has never worked. I've tried A LOT to get this working, so the default SBS settings are gone.. Is Outlook Anywhere suppose to work out of the box with a Small Business Server?

Note: We are using a Self-Signed Certificate

Is there a way to completely reset all certificates and URLs for Autodiscovery, RPC, .. so I can start from scratch? Or can somebody tell me how to troubleshoot this problem. It's a mystery for me.

Some things that I've tried:

  • Disable Outlook Anywhere and Enable it again (used hostname: remote.sbsname.com)
  • Tested the Autodiscovery (Remote Connectivity Analyzer says OK, see picture)
  • In the beginning my Autodiscovery wans't working, but I think I got that fixed.
  • Should I take mail.sbsname.com or remote.sbsname.com ?

Autodiscovery

  • RPC/HTTP-Test fails enter image description here

Thank you very much.

HopelessN00b
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Jente
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    Even though I've used the Exchange tool countless times, I still have no idea what that says. English translation would help your cause. – DanBig May 23 '14 at 12:06
  • Also, the biggest question, what kind of SSL cert are you using? UCC, standard or wildcard? If you aren't using UCC, you will be in for a TON of extra work. – DanBig May 23 '14 at 12:07
  • DanBig, I will try to translate the text. Is there a way I can surf to the analyzer and get the English version? – Jente May 23 '14 at 12:27
  • Also, I'm using the default certificates that are made by the SBS server, with the 'Fix My Network' wizard. Self signed. – Jente May 23 '14 at 12:39
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    Self signed are going to fail with the Exchange tester. Also, you will need to manually install them on your clients before the HTTP/RPC will work. Your best bet is to purchase a UCC cert from a 3rd party. – DanBig May 23 '14 at 12:46
  • DanBig, I installed the certificate on the client, but no luck. Can I reset the Outlook Anywhere settings? – Jente May 23 '14 at 12:49
  • This is going to require some more in depth discovery of your configuration, and it sounds like you may need someone to work with on site that is familiar with Exchange and Autodiscover. – DanBig May 23 '14 at 13:05

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