Hello Customer,

From the post log, it seems that this issue should be related to Exchange
Server rather than Outlook client as Out of Office Assistance also doesn't
work in OWA.

For Exchange Server side questions, I recommend you submit it to the
managed newsgroup microsoft.public.exchange.admin as there is more
qualified pool of respondents who can give you suggestions. Meanwhile,
other partners who visit the newsgroups regularly can either share their
knowledge or learn from your interaction with us.

Having said that, I would like to provide some general information for your
reference:

As I know, OOF to Internet is disabled on Exchange by default. Here is an
article for this issue and for how to enable OOF to Internet

323665 Internet Recipients Do Not Receive Out-of-Office Message
http://support.microsoft.com/?id=323665

Also you can enable Message tracking on the server and then send a test
email to the one who has enabled OOF assistant from his client. After
that, please go to Message tracking center to check if the OOF auto reply
has been sent from the client already.

More Info about Message tracking he

246856 How to enable message tracking in Exchange 2000 Server and in
Exchange Server 2003
http://support.microsoft.com/?id=246856

Hope this helps.

Regards,

Ada Pan

Microsoft Online Partner Support
Get Secure! - www.microsoft.com/security
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