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Outlook Anywhere prompting for password and cant authenticate without adding domain to username field

Posted on 2013-06-11
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Last Modified: 2013-06-11
Hey guys,

We have our Outlook clients all configured to use Outlook Anywhere and if there is a network drop-out for any reason (which seems to happen a lot but that's a question for another time) they get prompted with a Microsoft Outlook authentication window with the username already filled in.

E.g.  
username
[emptypassword]

If all they do is enter their password they cannot authenticate.

e.g.
username
password

Only if they add the company domain name to the front of their username can they successfully authenticate.

E.g.
domain\username
password

Now I know that this could be solved with training but I don't believe that is our only option. That and the FC at work didn't like that answer.

I would like to know if there is a way to configure something on our Exchange 2010 server or Outlook so either the domain is already entered, negating the need for the user to add it manually, or if there is a fix to this issue.

This issue seems to effect all Outlook clients, 2003, 2007 and 2010 on both Windows XP, Win 7 32 bit and 64 bit. All of these machines are on the company domain. It happens when on the company LAN as well as when off-site.

Forgive me if I don't have all the details for the configuration handy, I didn't configure this service so I don't know it intimately. But I do know that we are using basic authentication for Outlook Anywhere.

I really appreciate any assistance I can get on this.

Thanks in advance.
AC.
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Question by:defecta
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Accepted Solution

by:
Andrej Pirman earned 500 total points
ID: 39239723
Weird. Must have been some authentication issue.

Test the connectivity: https://www.testexchangeconnectivity.com/

Try this (last post): http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/12602ae2-8f09-4b03-8343-b334bc37dddf



Also, it might be Autodiscover issue (if TEST from above fails on autodiscover).

Outlook uses Autodiscover constantly. It isn't just the configuration of Outlook, it is also the availability service (Out of Office and Free/Busy information).

A single name certificate can only be used if your external DNS provider supports SRV records - otherwise you need to use a UCC certificate.

With regards to Outlook Anywhere, it should be simply a matter of enabling the feature. Nothing else.

Therefore I would suggest you reinstall the feature.
- Disable Outlook Anywhere in Exchange. Wait for the event log entry that reports it is disabled.
- Then remove the RPC Proxy through Windows.
- Run IIS RESET.
- Reinstall the RPC Proxy component.
- Then re-enable the Outlook Anywhere in Exchange. Wait for the event log entry to appear in the event viewer and test again.

Ideally you should get autodiscover to work correctly.
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Author Comment

by:defecta
ID: 39239811
Thanks for that tip Lasby.

I think you hit the nail on the head with Outlook Autodiscover.

In the last year we have had a complete infrastructure overhaul which has seen our email server merge with our parent company and there seems to be quite a few little details like this that don't work still.

If I use my email address with the parent company domain rather than my email with my companies domain, the autodiscover succeeds.

Otherwise with all other credentials the same, the only change is my email address, the auto discover fails.

Maybe this is topic for another question but how do I go about configuring an autodiscover for our email domain without interfering or breaking the current one? We have our own mail server here if that helps things.
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LVL 10

Expert Comment

by:Mohammed Rahman
ID: 39240157
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Author Closing Comment

by:defecta
ID: 39240176
Thanks Labsy. You reply has given me the information I need to resolve this.

Its the autodiscover process that is the cause of our issues. I have just discovered that the other businesses within the group that are not using the parent companies email domain are all having the same issue.
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