Outlook/Exchange 2007 Out of Office not working. Neither is Test Email AutoConfig.

adminknight used Ask the Experts™
Working thru most questions and posts about the OOF not working in Outlook 2007 on an Exchange 2007 server say first thing to test email autoconfig in Outlook. When I do instead of getting a list of info, i get a message that say:
Autoconfiguration was unable to determine your settings!

I'm reading white papers and studying up on Exchange as I'm a bit rusty. Could use some help though.
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There can be many reasons why autodiscover doesn't work.
Has it ever worked?
Do you have a commercial SSL certificate in place?
Has anything been changed on the server

Internally, on the domain, autodiscover should come off the domain, so name resolution of autodiscover.example.com shouldn't be a problem.

You haven't really provided enough information to work on.
Multiple servers, anything unusual about the configuration?

This blog posting has a good write up, but the images are broken.

what does it return when you run from the exchange shell

test-outlookwebservices username | fl


Worked for about a year.
No changes made to or in exchange
No commercial SSL
Single domain, single server

Badgermike: Results

Id      : 1003
Type    : Information
Message : About to test AutoDiscover with the e-mail address myemail.email.com

Id      : 1013
Type    : Error
Message : When contacting https://FQDN.domain.com/Autodiscover/Autodiscover
          .xml received the error The underlying connection was closed: An unex
          pected error occurred on a send.

Id      : 1013
Type    : Error
Message : When contacting https://FQDN.domain.com/Autodiscover/Autodiscover
          .xml received the error Authentication failed because the remote part
          y has closed the transport stream.

Id      : 1006
Type    : Error
Message : The Autodiscover service could not be contacted.

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do you have outlook web access enabled....I mean can you log into owa without issue?

Also what happens in an outlook client when you hit send receive - download address book - global address list?

Also if you could post the return of:

get-webservicesvirtualdirectory | fl


OWA is not enabled.
When downloading GAB

Task 'Microsoft Exchange' reported error (0x8004010F) : 'The operation failed. An object cannot be found.'

Results of get-webservicesvirtualdirectory

InternalNLBBypassUrl          : https://FQDN.domain.com/ews/exchange.asmx
Name                          : EWS (Default Web Site)
InternalAuthenticationMethods : {Ntlm, WindowsIntegrated}
ExternalAuthenticationMethods : {Ntlm, WindowsIntegrated}
BasicAuthentication           : False
DigestAuthentication          : False
WindowsAuthentication         : True
MetabasePath                  : IIS://FQDN.domain.com/W3SVC/1/ROOT/EWS
Path                          : E:\Program Files\Microsoft\Exchange Server\Clie
Server                        : EXCHANGE
InternalUrl                   : https://FQDN.domain.com/EWS/Exchange.asmx
ExternalUrl                   :
AdminDisplayName              :
ExchangeVersion               : 0.1 (8.0.535.0)
DistinguishedName             : CN=EWS (Default Web Site),CN=HTTP,CN=Protocols,
                                CN=EXCHANGE,CN=Servers,CN=Exchange Administrati
                                ve Group (FYDIBOHF23SPDLT),CN=Administrative Gr
                                oups,CN=OURCN,CN=Microsoft Excha
Identity                      : EXCHANGE\EWS (Default Web Site)
Guid                          : fae40b6e-7cc9-4df2-a332-04b6d58665f8
ObjectCategory                : domain.com/Configuration/Schema/ms-Exch-Web-Ser
ObjectClass                   : {top, msExchVirtualDirectory, msExchWebServices
WhenChanged                   : 6/5/2008 3:51:21 PM
WhenCreated                   : 4/29/2008 9:54:39 AM
OriginatingServer             : DCXX.domain.com
IsValid                       : True
is this an internal client or an external remote client?


all internal.
I can't see anything in your webservice test - other than that people say it could be a cert error or if asp.net registered for 32 bit instead of 64....


I had the exact same error that I had to fix by:

Uninstall IIS/Reinstall IIS....Uninstall CAS server role/Reinstall CAS role/Rebuild the virtual directories via emc.

for our setup I had to also rebuild legacy virtual directories via emc for our one mac that works off the old /exchange directory, enable webdav in IIS extensions for the entourage client, and since we use the anti-spam agents I had to uninstall/reinstall them.

We have one exchange server with all roles  well except for edge.

I was trying my best to research the solution, when we had the issue I spent like 2 weeks, I just spent about an hour and a half and didn't find anything I was hoping too because I though since I fixed months ago there should be something better than a CAS reinstall but I can't find it. I wish I could have saved you some time. Hopefully someone out there has something better. It took a couple hours to complete and did the trick ....Good luck to you....



Reinstall of IIS: Anything special to it on an Exchange server? Do I need to do anything before i uninstall or after I reinstall?

The CAS role. What is involved with reinstalling it?


Found this:
Only question is when recreating virtual directories do I use FQDN or not?
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If you are going to reinstall IIS, and then CAS, after doing so I would test it again before making any changes to the system. Autodiscover should work internally correctly without any changes to the Exchange configuration.

Here is the documentation that I used to unistall ISS and CAS and then reinstall if you are going that route.


Scroll down to the Exchange 2007 portion.

I followed everthing to a T - the only non standard things for me that popped up were renabling webdav - for our entourage user / and the reinstall of the antispam agents.


Badgermike, that's the same one I posted above. I just was curious before I started it mentions at the bottom, under Recreating Virtual Directories to use the server and DC name. Do I use FQDN or not?
Sorry I was typing to fast - I did not use FDQN -

Issue wasn't IIS, was an issue with the certificates. Working now. Thanks for the info though.

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