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redmanbrosFlag for Australia

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Automatic reply (out of office) not working for SBS 2011

I have an SBS 2011 server with Exchange 2010.

Automatic reply feature is not working for any mail account.

I have enabled it in Outlook Web Access, created an AutoDiscover SRV record in the DNS and run the Exchange Remote Connectivity Analyzer (www.testexchangeconnectivity.com).

I am using a self-issued certificate for the SBS server.

The results of the analyzer pass when "ignore trust for SSL" is unticked but fails when it IS ticked with the following error:

===================
ExRCA is attempting to build certificate chains for certificate CN=mail.mydomain.com.

A certificate chain couldn't be constructed for the certificate.

Additional Details

The certificate chain couldn't be built. You may be missing required intermediate certificates.
=================

I am not even sure if the failure of Automatic Reply is based on the autodiscover configuration as I have another SBS Server (different company) running that has been set up out of the box without any Autodiscover DNS or SRV record configured, with a self-signed certificate and it fails the Exchange Remote Connectivity test but it still works with Automatic Reply!

I know that the Automatic Reply is a feature that only delivers one email address per sender email and during my testing I once got the server to deliver one Automatic Reply. However creating a new test user account and using different sender email addresses cannot get it to work and toggling the option in Outlook Web Access does not resend any automatic reply.

Thanks for your help in advance!
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Jeffrey Kane - TechSoEasy
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Autodiscover has a lot to do with OOF replies, so that definitely needs to be working properly.
Here is a good overview on how to make sure it is set up correctly:
http://www.thirdtier.net/2011/06/setting-up-autodiscover-for-sbs-2011/

For good measure you can also run the FixMyNetwork wizard.

Also, just so you know, when testing you can disable and re-enable Out of Office to allow an automatic reply to be sent to an address which has already been sent one.

Jeff
TechSoEasy
Did you test on internal or external recipients?

Check if automatic replies are activated in Exchange -> Organization configuration -> Hub Transport -> Remote Domains -> Properties on "yourdomain"

Check tabs "General" and "Message Format"
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ASKER

initsol: I have been testing this using external recipients. Just had a chance to test it internally and it is working internally as I received an automatic reply. The problem must be related to the external recipients?

I checked the "Hub Transport" properties and the value is set to: "Allow external out-of-office messages and legacy out-of-office messages ...". Is this the correct setting to allow external recipients? "Message Format" tab has "Allow automatic replies" ticked.

jeff: yes, I did go through that article beforehand and created an SRV record with correct DNS settings. I have tried to toggle the Automatic reply feature to get it to work again but to no avail. Shouldn't it work with a self-signed cert? My other SBS server is working ok without the need for a 3rd party cert.

Thanks for your help.
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initsol
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jeff: yes, you are right. The Exchange Connectivity Test works only if "Ignore trust for SSL" is ticked. This is not what I described in my original post. Apologies for the confusion. I ran the wizards again and the SBS Server automatically chose the remote.mydomain.com as the external domain name for the server. It was originally mail.mydomain.com. So I had to create an "A" record to point to "remote.mydomain.com". After that, my initial test of Automatic Reply produced a positive result (I received an out of office reply) but subsequent testing to an different email address failed. And even disabling and then renabling Automatic Reply for the email address that worked initially, has failed. So why should it work once for one email address and then stop working?

initsol: I haven't created a new send connector yet but I did change the way messages are sent using DNS instead of routing through a smart host. I got a few out of office emails coming through now but I will check with an employee to do more rigorous testing and let you know.
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Nice!
Have fun :)
Comments were helpful in achieving the desired result in my final comment.