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Exchange 2010 no Autodiscover or outlook anywhere

I recently setup Exchange 2010 on Windows 2008 R2 Std VPS server. The install went fine and most of the services are working but I can't get Autodiscover or Outlook Anywhere up and running. I've spent the last week searching the web and have yet to find and issue and even gave up at one point wiped reset the server and started over. Still I can't get either service working.

When I visit the autodiscover page it does prompt for a username and password but it does so a couple times and then I get the following error:
<?xml version="1.0" encoding="utf-8" ?>
- <Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
- <Response>
- <Error Time="12:58:57.2105396" Id="2561661876">
  <ErrorCode>600</ErrorCode>
  <Message>Invalid Request</Message>
  <DebugData />
  </Error>
  </Response>
  </Autodiscover>


TestExchangeConnectivity.com gives me the following:

      ExRCA is attempting to test Autodiscover for chad@masm.org.
       Testing Autodiscover failed.
       
      Test Steps
       
      Attempting each method of contacting the Autodiscover service.
       The Autodiscover service couldn't be contacted successfully by any method.
       
      Test Steps
       
      Attempting to test potential Autodiscover URL https://masm.org/AutoDiscover/AutoDiscover.xml
       Testing of this potential Autodiscover URL failed.
       
      Test Steps
      Attempting to test potential Autodiscover URL https://autodiscover.masm.org/AutoDiscover/AutoDiscover.xml
       Testing of this potential Autodiscover URL failed.
       
      Test Steps
       
      Attempting to resolve the host name autodiscover.masm.org in DNS.
       The host name resolved successfully.
       
      Additional Details
      Testing TCP port 443 on host autodiscover.masm.org to ensure it's listening and open.
       The port was opened successfully.
      Testing the SSL certificate to make sure it's valid.
       The certificate passed all validation requirements.
       
      Test Steps
      Checking the IIS configuration for client certificate authentication.
       Client certificate authentication wasn't detected.
       
      Additional Details
      Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
       Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
       
      Test Steps
       
      ExRCA is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.masm.org/AutoDiscover/AutoDiscover.xml for user chad@masm.org.
       ExRCA failed to obtain an Autodiscover XML response.
       
      Additional Details
       An HTTP 401 Unauthorized response was received from the remote Unknown server. This is usually the result of an incorrect username or password. If you are attempting to log onto an Office 365 service, ensure you are using your full User Principal Name (UPN).
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Chad Penney
Asked:
Chad Penney
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1 Solution
 
Simon Butler (Sembee)ConsultantCommented:
The error you got when browsing to Autodiscover is to be expected, so should be discounted as any kind of test.
The errors from the external test indicate that you don't have a DNS record for autodiscover in place. You need autodiscover.example.com pointing to your external IP address.

Do you have an SSL certificate in place?

Simon.
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Chad Penney.Net Techincal Team LeaderAuthor Commented:
I do have a DNS record both internally and on our external DNS for autodiscover.

Yes I do have a UC Certificate installed on the server as well.
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Simon Butler (Sembee)ConsultantCommented:
Does the Autodiscover external record resolve to the correct place?
Have you changed anything away from the default configuration, because the error is unauthorised, which would either say you had the wrong password, or the authentication type isn't default.

The first thing I would therefore do, if you are sure the username/password combination was correct, is to reset the Autodiscover virtual directory. On Exchange 2010 SP2 there is a wizard for doing so in the Client Access section of EMC.

Simon.
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Chad Penney.Net Techincal Team LeaderAuthor Commented:
Yes it does resolve to the right server as does the default or MASM.org. I didn't make any changes to the default virtual directory before I started testing but had int he process of trying to fix this issue so I went ahead and did the rest but it didn't have any affect on the results. Still getting the same error.
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Simon Butler (Sembee)ConsultantCommented:
Create a fresh account, and ensure that it is just a regular user rather than an existing user. The error you are getting is an authentication error.

This is one of those things that either works, or it doesn't, no middle ground. Therefore you have to rule out all of the obvious stuff.
It could be that something is blocking the traffic between the internet and your Exchange server - some firewalls can mung the authentication traffic for example.

Simon.
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Chad Penney.Net Techincal Team LeaderAuthor Commented:
Tried creating a new user and that didn't make any difference. I'm still getting the same error. This is gotten to be really frustrating.
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Simon Butler (Sembee)ConsultantCommented:
If a new account has the problem then it could be something server side, or external to the server. Have you tested it internally to see if things work?
You would probably need a split DNS system so that the Autodiscover DNS records resolve internally to the server's internal IP address, and a workstation off the domain so it must use DNS. If it works internally then you know the problem is outside of Exchange.

Simon.
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