activate auto responder in Outlook Anywhere


I have an enterprise with the domain  It is running an Exchange 2013 standard mailserver called  This is the actual hostname and it is accessable both from the inside and the outside. is registered in DNS and points to the external IP.  The certificate mentions both names.

This enterprise is using it's mailhost also for several subsidaries, which are using a different maildomain, say
There are several of these.  Each employee has a mail address, but the main address is always

The workstations are not AD members (some are / some are not - does not seem to make a difference).
Outlook Anywhere is used all over.

Users are fine connecting with the server.  Everything seems to work except:
- users cannot activate their auto responders
- users cannot share their calendars through email.

Googeling suggests that autodiscover is not in place correctly, but speaking for the enterprise, it is! for each of the maildomains is however neither pointed to the mailhost nor included in the certificate.

Do I have any chance to get this to work smoothly without issuing a certificate with 50+ names in it?

Ralph ScharpingDigital TherapistAsked:
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Mohammed KhawajaManager - Infrastructure:  Information TechnologyCommented:
Have tried running Exchange Connectivity test to see if there are any errors.  Perform the tests by going to

Perform Microsoft Exchange Web Services Connectivity Tests
Simon Butler (Sembee)ConsultantCommented:
If you have users with their primary email address in another domain, then you have to put something in place for Autodiscover in that domain. The client will not know about Autodiscover in the primary domain - the fact the users have an address in that domain means nothing. It is only the primary domain that is used.

Therefore you need to confirm do you have one of the following for that second domain.

a. In the SSL certificate, listed as one of the hosts, with the relevant A record in place?
b. In the external DNS for the domain, you have SRV records in place (if the end users come on site with non-domain members then you will need them internally as well).
c. You have setup HTTP redirect for the second domain using a second web site on the Exchange server, with a separate IP address.

If you haven't done any of those, then that is the problem - you haven't covered Autodiscover for that domain externally.

Ralph ScharpingDigital TherapistAuthor Commented:
So, if I got you right, there is no way to get this to run smoothly unless I include every maildomain in the certificate and do a full autodiscover configuration.  Right?
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Simon Butler (Sembee)ConsultantCommented:
Every email domain in the certificate is one way.
However if you have lots of domains then you can use the other methods that Microsoft have provided. Autodiscover is not optional - you need to put something in place for Autodiscover.

However be aware that if you have mobile devices, support for Autodiscover is very mixed. Most of them will support the in the SSL certificate method - the other methods are not supported by all devices.

Ralph ScharpingDigital TherapistAuthor Commented:
Perfect.  Do you happen to have a detailled howto for option b?  It seems the most feasable for my use.
Simon Butler (Sembee)ConsultantCommented:
Microsoft have guides on all of the methods on TechNet and MS KB.


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Ralph ScharpingDigital TherapistAuthor Commented:
Perfect - thank you!
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