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Autodiscover SBS2011

Posted on 2014-09-05
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Last Modified: 2014-11-10
Hi,

I have and SBS cert that has autodiscover.mydomain.com and smtp.mydomain.com for example.

Autodiscover has an A record to the router firewall etc with 443 and 80 open.

When I connect to the account via Outlook 2013 it prompts for credentials and will only work if I put domain\user and password which connects fine.

If I do via iphone it wants to know the smtp.mydomain.com and the domain credentials to successfully connect, which again works.

Why will it not just accept the email address and password and just work without needing domain\user or the server name on the iphone?

When I use the remote connectivity analyser for Autodiscover and Exchange ActiveSync test I get the below:

Attempting to test potential Autodiscover URL https://domain:443/Autodiscover/Autodiscover.xml 
  Testing of this potential Autodiscover URL failed.
 
 Additional Details


 Attempting to test potential Autodiscover URL https://domain:443/Autodiscover/Autodiscover.xml 
  Testing of this potential Autodiscover URL failed.
 
 Additional Details
 

 Attempting to contact the Autodiscover service using the HTTP redirect method.
  The attempt to contact Autodiscover using the HTTP Redirect method failed.
 
 Additional Details
 
 
 Attempting to contact the Autodiscover service using the DNS SRV redirect method.
  The Microsoft Connectivity Analyzer failed to contact the Autodiscover service using the DNS SRV redirect method.
 
 Additional Details
 
 


 Checking if there is an autodiscover CNAME record in DNS for your domain 'domain' for Office 365.
  Failed to validate autodiscover CNAME record in DNS. If your mailbox isn't in Office 365, you can ignore this warning.
   Tell me more about this issue and how to resolve it
 
 Additional Details
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Question by:monarchit
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3 Comments
 
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Accepted Solution

by:
Simon Butler (Sembee) earned 500 total points
ID: 40306128
Email address isn't a valid username for Exchange. Simple as that.
You can make the usernames look like email addresses, but if they are the same, that is a coincidence.

You do that by adding your public domain name to the list of UPN suffixes:
http://technet.microsoft.com/en-gb/library/cc772007.aspx

The change each user's UPN value to match their email address.
SBS will not be able to do that automatically - so after creating users you will have to change their UPN value manually using ADUC.

The password prompt in Outlook when external is to be expected - by default Outlook Anywhere uses Basic Authentication, which generates a password prompt.

Simon.
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Author Comment

by:monarchit
ID: 40312653
Any idea why it wouldn't pick up autodiscover on the phone and asked for the external URL?
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LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 40318148
Autodiscover on ActiveSync devices is very hit and miss, even within the same OS versions. I have seen it work on some Android devices, and not on others. Ditto for iOS. The most reliable ones seem to be Windows Phone (naturally) and Blackberry OS 10 devices.

Simply put, I tell clients to expect it to NOT work and provide instructions to the end users for manual setup.

Simon.
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