Is there any way to turn on my "Out of Office" automatic replies when an event in the calendar is marked "out of office"?

It is not possible. Out-of-office replies are sent by Exchange. There is no Exchange feature that reads calendar events in users mailboxes.

Calendar reminders are sent by Outlook, there is no link between the two that can be turned on.

This is not a walkthrough, but it does provide the steps required in order to get it working. If anyone actually completes this, I would love to see them post it.

Use the Rules Wizard. On every inbound mail, you will want to run a script.

The script you will want to run is an Outlook VBA script, which will perform the following actions:

• Check for any current meetings
• For every current MeetingItem object found, you will want to check the busyStatus of the object to see if it matches olOutOffice
• Finally, set your out of office status appropriately or reply back with a custom "I am in a meeting" message.

Additional References:

• http://www.dimastr.com/redemption/rdo/RDOOutOfOfficeAssistant.htm
• http://www.outlook-answers.com/microsoft/Outlook-Program-VBA/29286942/automatic-activation-of-outofoffice-mesage.aspx
• http://www.slipstick.com/outlook-developer/code-samples/set-reminder-meeting-request/

Good luck and godspeed!