How do I fix Autodiscover internal 500 error?

Posted on 2008-06-23
Last Modified: 2008-09-17
This issue was originally brought to my attention when one of the users was unable to use the Out of Office Assistant in Outlook 2007.  I have read every article I can find regarding the apparently common Autodiscover problems on Exchange 2007, but none of them deal with this error specifically:

From Exchange Management Shell, when I run Test-OutlookWebServices:

Id      : 1019
Type    : Information
Message : Found a valid AutoDiscover service connection point. The AutoDiscover
           URL on this object is

Id      : 1013
Type    : Error
Message : When contacting
           received the error The remote server returned an error: (500) Internal Server Error.

Id      : 1006
Type    : Error
Message : Failed to contact AutoDiscover

I've seen several examples where people get 403 forbidden errors and have been able to avoid that problem..  I  also have the problem where line 64 of the web.config file gives errors in the event log, but re-installing CAS as recommended does nothing.

Started with a self-signed SSL cert, but now moved onto a GoDaddy cert in an effort to help.

Any help or advice would be greatly appreciated as I've exhausted everything I can find on the subject.
Question by:drewmack1
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Author Comment

ID: 21852658
Some additional items to consider:

1) When I open I get the following message:
Server Error in '/Autodiscover' Application.

Configuration Error
Description: An error occurred during the processing of a configuration file required to service this request. Please review the specific error details below and modify your configuration file appropriately.

Parser Error Message: Could not load file or assembly 'Microsoft.Exchange.Clients.Owa' or one of its dependencies. The system cannot find the file specified. (D:\Program Files\Microsoft\Exchange Server\ClientAccess\owa\web.config line 64)

Source Error:

Line 62:             <!-- OWA HTTP Modules -->
Line 63:             <httpModules>
Line 64:                   <add type="Microsoft.Exchange.Clients.Owa.Core.OwaModule, Microsoft.Exchange.Clients.Owa"
Line 65:                         name="OwaModule"/>
Line 66:             </httpModules>

Source File: D:\Program Files\Microsoft\Exchange Server\ClientAccess\owa\web.config    Line: 64
I have seen others post this identical message and their solution was to re-install CAS.  I have tried this several times to no avail.

2) When I run the "Test Email AutoConfiguration" wizard from Outlook 2007 I get this under the results tab:
Autoconfiguration was unable to determine your settings!
and this under the Log tab:
Attempting URL found through SCP
Autodiscover to starting
Autodiscover to FAILED (0x800C8204)

If I find any other errors I will post them.  Thank you!
LVL 16

Expert Comment

ID: 21868265
Was the godaddy cert a UCC cert or did you use a regular cert?

With Exchange 2007, you need what's called a UCC or SAN certificate which encompasses multiple domains within one certificate.

Author Comment

ID: 21868311
No this is just a normal cert.  What are the requirements and steps for setting up a UCC cert in Exchange 2007?  Is there any way to tell if this will solve the problem before making the purchase?
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LVL 16

Accepted Solution

LegendZM earned 500 total points
ID: 21868487
For exchange 2007 you need what is called a UCC certificate:

Multiple Domain Certificates, also called Unified Communications Certificates (UCC), provide the most flexible class of SSL Certificates today by securing multiple domain names with one certificate.
Secure up to 100 domain names on one certificate.
Save money because the cost of one Multiple Domain Certificate, with additional domain names, is less than the cost of individual certificates for each unique domain name.
Compatible with Microsoft Exchange Server 2007 and Microsoft Communications Server.
Simplifies the process of managing multiple certificates with varying expiration dates.
Our Single, Multiple Domain and Subdomain certificates all use the same rock-solid, 256-bit encryption technology, proving that your Web site is a secure place for customers to conduct business.
NOTE: The UCC Certificate is ideal for Communication Server, Exchange Server and other Enterprise Applications, as well as for single companies or entities with many related URLs. This Certificate is not recommended for use with sites completely separate from each other (e.g. a network provider who builds Web sites for competitors).

You can no longer use 1 certificate for the domain 'owa or mail.your

you need 1 certificate for multiple domains
outlook 2007 uses which you need a cert for
owa uses it's own, etc

So instead of purchasing multiple certs, you need a UCC cert that covers all of it.

Common name as in what the clients are already using. So if the clients are all configured to use then that needs to be in the certificate.

UCC certificate  and that supported five names (This can go up to 100 possible domain names), so I adjusted the list to: (which was the common name)
server (ie just the NETBIOS name).
LVL 16

Expert Comment

ID: 21868502
You need to generate the command from exchange powershell, here's a web based tool that will help you.

and a MS KB on the command used:
Once done , use this command to import the certificate in Exchnage PS:

Author Comment

ID: 22035319
Okay I will give this a try and go from there.

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