OOF not working and Autodiscovery messed up - Part 1

I have had a long email chat with a guy in the US. In fact, I took offline a thread about messed up Autodiscovery and combined with a similarish problem experienced by fellow Tek Tips member Mark MacLachlan.

 

John’s problem was that autodiscover was refusing to cooperate and he’d even reformatted and reinstalled the OS. He was getting a 500-19 error in Autodiscover which was pointing to a problem with a malformed or corrupt web.config file in /Autodiscover.

 

Testing went as follows:

When I run Test Email Autoconfiguration, it finds the url through SCP, starts then ends with http status code 500.

Here are the results from Test-Outlook Services:

[PS] C:\Windows\System32>test-outlookwebservices |fl

Id      : 1003

Type    : Information

Message : About to test AutoDiscover with the e-mail address Administrator@domain.local.

 

Id      : 1007

Type    : Information

Message : Testing server test.domain.local with the published name https://test.domain.local/EWS/Exchange.asmx & .

 

Id      : 1019

Type    : Information

Message : Found a valid AutoDiscover service connection point. The AutoDiscover  URL on this object is https://test.domain.local/Autodiscover/Autodiscover.xml.

 

Id      : 1013

Type    : Error

Message : When contacting https://test.domain.local/Autodiscover/Autodiscover.xml received the error The remote server returned an error: (500) Internal Server Error.

 

Id      : 1006

Type    : Error

Message : The Autodiscover service could not be contacted.

 

So now what?