Exchange 2010 DAG - Out of Office Not sending to external recipients

We've recently migrated a client to Exchange 2010 from 2003. We are using outlook 2003 clients on floor. Just got word that the OOF not flowing to external recipients (even when configured via OWA).  I have selected the option within OWA to send out of office replies to internal and external recipients. I have checked my spam gateway (which is have a send connector via exchange) and there is nothing there. It's as if exchange isn't even sending the message at all. Message tracking only shows out of office replies being sent/generated for internal domain users.
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Check the automatic replies
You may need to set it to legacy
EncinitasAuthor Commented:
we are setting within OWA (outlook2010 OWA). This doesn't seem to be relevant.
Are they  setting both  an external and internal out of office?
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External oof
EncinitasAuthor Commented:
Yes, both. I have tried myself with my own account and have verified this via OWA. I do not see anything stuck in my anti-spam appliance filter so nothing seems to be generated and sent out via WAN to external sources.
Check this setting too on the remote domains remote domains
EncinitasAuthor Commented:
Confirmed. Also on message format tab under "message format options" i have all options checked except "use message text line wrap at column".
what is the status for the read-receipts for the external domains? Are they facing the same behaviour?

Can you by-pass your spam-gateway for a while and test again?

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EncinitasAuthor Commented:
I tried sending several messages with read receipts to my gmail account. It did not function (i did not receive an email). I will try to open up a case with my mail gateway vendor to verify that the gateway is not blocking anything. I will post as soon as soon as possible (probably within the next 2-3 hours.
EncinitasAuthor Commented:
i wanted to clarity my previous post. I did receive an email, but no read receipt.
EncinitasAuthor Commented:
Spam appliance is not blocking, verified by opening case w/vendor. The problem seems to reside on exchange, i just don't know where to look.
IMO, when exchange can send the read-receipts and OOF for any messages received on that mailbox.

I dont think exchange has got an option to identify and seperate the internal & external messages during this OOF,read-receipts stage

Reason: When you send an email to external (Or OOF, read-receipts to the any sender (external))...those mails get identified and stamped outside the mailbox @ categorizer

Still is there a chance to by-pass the spam-appliance for few hours atleast to get the behaviour?

> Can you check with any other exchange-servers\clients using the spam-appliance for their OOF,Read-receipts behaviour

EncinitasAuthor Commented:
No changes. I have opened up a case with Microsoft. I will update the ticket as soon as we have closure on this so perhaps others can benefit from this post.
EncinitasAuthor Commented:
This was the problem. Mail appliance vendor stated that their appliance wasn't the problem, well it was! We had BATV enabled. After disabling this did the trick! Thanks for all of the help!
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