SBS 2011 (Exchange 2010) AutoResponder Not Responding (is enabled in OWA)

Hi all,

We have a small customer running SBS 2011 - everything is working fine except that automatic replies (Out Of Office) never sends any messages.  Email are received by our users and the users can reply to the senders so it's not a routing or mail flow issue - the SBS server just never seems to prepare and send a response when automatic replies are enabled.

I have tried enabling/disabling via Outlook and OWA, checked for updates, rebooted server, etc.

Any ideas would be hugely appreciated

Thanks

Bob
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Mango-ManAsked:
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Raj-GTConnect With a Mentor Systems EngineerCommented:
It should be the third one. The remote domain is a wildcard in this case as you are using the same OOF policy for all external domains. You can get crafty and create different policies for different domains if you want (i.e. No OOF for yahoo.com, hotmail.com or gmail.com etc.)

Can you run the following and check if all mailbox users have external oof enabled.
get-mailbox * | ft alias, *oof*

If it is then can you try the following and see what happens please.
1. Create a new user account and enable OOF for internal and external users in Outlook
2. Send e-mail to this user from an internal account and an external account
3. If you don't get any OOF for the above, repeat the steps but this time create the account on a new mailbox database

It's also worth checking any anti-spam and anti-virus add-ons you may have to see if they are blocking/dropping OOF.

Thanks,
Raj

P.S. Apologies for the multiple edits :-)
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Mango-ManAuthor Commented:
Just as an update, I've continued to research this issue and have performed the following:

1) Checked for Updates, Rebooted Server, Sent Numerous Tests after enabling/disabling OOF

2) Confirmed that Out of Office is showing as enabled in OWA (so not just an Outlook Display Bug): Yes

3) Used Exchange Powershell to confirm Exchange is seeing OOF as enabled by running get-mailbox 'user.name' | get-mailboxautoreplyconfiguration | select identity, autoreplystate¿, it confirmed it was enabled.

4) A bit of research said that if auto configuration isn't working properly it can cause problems because Outlook uses this to set OOF - sure this isn't the problem because as above, Exchange is seeing it enabled but just not responding BUT just in case, I opened port 80 on the server (apparently advisable for more reliable autodiscover).  This had the benefit of OWA working better in Chrome (prior to this, the OOF options weren't working, had to use IE).

5) Performed the following tests as per this post with the same issue:

  5a) Setup User's mailbox on my copy of Outlook so I could use the CTRL + Click Outlook Tray Icon¿ trick to get to the ¿Test Email Auto-Configuration¿ option and confirm the OOF URL is ¿https://server.companyDomain.com/EWS/Exchange.asmx¿

  5b) Confirmed that Require SSL is ticked on the virtual directory EWS in IIS
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Raj-GTConnect With a Mentor Systems EngineerCommented:
One more thing to check is under Exchange Management Console  > Organization configuration > Hub Transport > Remote Domains. Check and see if you have OOF enabled here.
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Mango-ManAuthor Commented:
Hi Raj,

Thanks for your help - I must admit I looked at this but couldn't work out which option to go for as they appear to say you can only have internal or external.  I've tried the third and fourth options, restarting Exchange Mailbox Assistants service in between but no joy.

I've attached a screenshot of what I see - I though it was a little odd that the domain is simply a wildcard?

Screenshot of SBS > Organization Configuration > Hub Transport > Remote Domain properties
Thanks

Bob
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Mango-ManAuthor Commented:
While this wasn't my problem - these are great steps to follow to solve the issue - for me we discovered that MailEssentials Online had - bafflingly - taken the decision to block all outbound Out of Office emails.
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