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YorkData
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autodiscover exchange 2010 server 2008 R2 error 500

We are trying to setup autodiscover on our exchange server and are having issues. test exchange remote connectivity is failing on the last step. I have checked internal and external urls, rebuild the autodiscover virtual directory and when we go to the web address externally it asked for credentials and then displeys the error 600 which I believe is correct.

Any ideas? See output form connectivity tester below.

The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.xxxxxxx.com:443/Autodiscover/Autodiscover.xml for user ohare@xxxxxxx.com.
       The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
       
      Additional Details
       
An HTTP 500 response was returned from Unknown.
HTTP Response Headers:
Content-Length: 0
Cache-Control: private
Date: Thu, 06 Nov 2014 14:50:24 GMT
Server: Microsoft-IIS/7.5
X-AspNet-Version: 2.0.50727
X-Powered-By: ASP.NET
Elapsed Time: 364 ms.
Exchange

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YorkData

8/22/2022 - Mon
Adam Farage

What are the permissions you have on the AutoDiscover Virtual Directory?

Get-AutoDiscoverVirtualDirectory | FL 

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YorkData

ASKER
Please see output below

[PS] C:\Windows\system32>Get-Au<wbr ></wbr>toDiscover<wbr ></wbr>VirtualDir<wbr ></wbr>ectory | FL

RunspaceId                      : d7a03a49-a3fb-40bc-9ecd-93<wbr ></wbr>47826590e6<wbr ></wbr>
Name                            : Autodiscover (Default Web Site)
InternalAuthenticationMeth<wbr ></wbr>ods   : {Basic, Ntlm, WindowsIntegrated}
ExternalAuthenticationMeth<wbr ></wbr>ods   : {Basic, Ntlm, WindowsIntegrated}
LiveIdSpNegoAuthentication<wbr ></wbr>      : False
WSSecurityAuthentication        : False
LiveIdBasicAuthentication       : False
BasicAuthentication             : True
DigestAuthentication            : False
WindowsAuthentication           : True
MetabasePath                    : IIS://server.xxxxxxx.local<wbr ></wbr>/W3SVC/1/R<wbr ></wbr>OOT/Autodi<wbr ></wbr>scover
Path                            : C:\Program Files\Microsoft\Exchange Server\V14\ClientAccess\Au<wbr ></wbr>todiscover<wbr ></wbr>
ExtendedProtectionTokenChe<wbr ></wbr>cking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
Server                          : server
InternalUrl                     :
ExternalUrl                     :
AdminDisplayName                :
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Default Web Site),CN=HTTP,CN=Protocols<wbr ></wbr>,CN=server<wbr ></wbr>,CN=Server<wbr ></wbr>s,CN=Excha<wbr ></wbr>nge Administrative Group (FYDIBOHF23SPDLT),CN=Admin<wbr ></wbr>istrative Groups,CN=First Organization,CN=Microsoft Exchange,CN=Services,CN=Co<wbr ></wbr>nfiguratio<wbr ></wbr>n,DC=xxxxx<wbr ></wbr>xxx,DC=loc<wbr ></wbr>al
Identity                        : server\Autodiscover (Default Web Site)
Guid                            : 42f80cd4-ad65-4603-9d05-a2<wbr ></wbr>172b300c8a<wbr ></wbr>
ObjectCategory                  : xxxxxxx.local/Configuratio<wbr ></wbr>n/Schema/m<wbr ></wbr>s-Exch-Aut<wbr ></wbr>o-Discover<wbr ></wbr>-Virtual-D<wbr ></wbr>irectory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualD<wbr ></wbr>irectory}
WhenChanged                     : 06/11/2014 14:44:33
WhenCreated                     : 06/11/2014 14:44:33
WhenChangedUTC                  : 06/11/2014 14:44:33
WhenCreatedUTC                  : 06/11/2014 14:44:33
OrganizationId                  :
OriginatingServer               : server.xxxxx.local
IsValid                         : True

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Adam Farage

Does it work externally, or no? I would run outlook.exe /rpcdiag from an external client and screen shot that for us. Your permissions look fine but I would imagine if its working externally then the testexchangeconnectivity.com website is giving issues (which I have seen before).
Your help has saved me hundreds of hours of internet surfing.
fblack61
YorkData

ASKER
No it doesn't work externally.

I ran rpcdiag however it didn't display any connections to the Exchange server at all. We're only enabling autodiscover to migrate over to to Office365 frustratingly!

Any other ideas?
Vinod Pawar

Please Set External and Internal Url for Autodiscover and also Make sure there is proper Entry of DNS for Autodiscover.*.domain.com.
After Setting this both check internally if your URL is working properly or you can check with Outlook with holding Cntrl key and Right click on Outlook Icon and click Test Email Autoconfiguration and you will found errors and get to root cause.
Adam Farage

@Vinod.. the AutoDiscover InternalURL and ExternalURL are *not* used at all. They are there due to the way the Exchange schema objects are extended for Virtual directories.
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YorkData

ASKER
I've done all of this however internally I am still getting the same error from test email autoconfig.

See attached image - we keep getting this error code 500. Out of office is also no longer working from within outlook.
YorkData

ASKER
I've set the autodiscovery urls within the client access not the autodiscovery virtual dir.
Adam Farage

no image attached, but if you have one with the Test-EmailAutoconfig I would love to see it. it would help us further troubleshoot this issue.
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William Peck
SOLUTION
Gareth Gudger

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YorkData

ASKER
I have tested this with multiple accounts, my admin one and normal user. I have also tried checking the inheritance tick box and removing admin count 1.

Please see image attached this time, how do I run the test-emailautoconfig? It doesn't seem to be a command in shell for Exch2010

I've rebooted the server this weekend to see if this helped but it hasn't.

Thanks for your help.
Capture.JPG
Gareth Gudger

What happens if you try to browse to your autodiscover URL in a browser?
YorkData

ASKER
I get an authentication screen and then the below - which I believe is correct

This XML file does not appear to have any style information associated with it. The document tree is shown below.
      <Autodiscover><Response><Error Time="08:25:09.8583711" Id="2245846463"><ErrorCode>600</ErrorCode><Message>Invalid Request</Message><DebugData/></Error></Response></Autodiscover>

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YorkData

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I found my own solution from other websites. I have added the solution to this thread.