Microsoft Outlook Out Of Office doesn't work
If your Out of Office does work internally but not externally then follow the instructions below
If you use the Out Of Office Assistant and turn on the out-of-office reply, the internal senders (on the local network) receive the automatic reply message, but external senders (on the Internet) may not receive the automatic reply.
PROBLEM
By default, the out-of-office reply to Internet recipients is turned off. Many administrators do not allow out-of-office replies to be sent outside the Exchange Server organization, so that unauthorized people do not know when users are out of the office.
RESOLUTION
To turn on out-of-office replies to the Internet, follow these steps:
On the Exchange server, start Exchange System Manager.
Go to Global Settings, and then click Internet Message Formats.
In the Details pane, right-click on your domain name, and then click Properties. The default SMTP domain is "*".
In the Properties dialog box, click the Advanced tab, and then click to select the Allow out of office responses check box. This turns on out-of-office responses to the Internet for the selected domain.
This was tested no Windows 2003 server with Exchange SP1 installed
You may need to restart the Simple Mail Transfer Protocol (SMTP) and Microsoft Exchange Routing Engine services
Server Tips / submitted by: N Rajsic
keyword:out of office assistant does not reply to external email addresses



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Foolishly attempt to do something that looks so simple, such as set up an Out Of Office Reply. Do it, test, but of course, it flat out doesn't work.
Spend 1-3 hours troubleshooting it. Google it, MSKB it, find and try 3-6 things, known issues, check Exchange settings, be sure Exchange is set to allow Out Of Office replies. etc.
Still no luck.
Give up. Buy a Mac and some properly functioning software that works like you expect it to.
The Exchange 2003 server is so smart that it will send the Out of Office message only one times per email address. So, it is a good idea to test the feature by sending mail from different account.
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