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Conflict denial messages not sent unless logged in

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I have a few accounts that are setup to manage conference rooms. Everything seems to work as expected except for one odd quirk that I cant figure out.

When creating a meeting request that conflicts with an existing appointment, the calendar does not send out the notification of denial. It wont add the calendar item either, which is good. I have found that it will only send the notification of denial after I log into a machine as the calendar user account and open outlook and it connects to Exchange. 

If I remain logged in and send a test that conflicts it responds right away. I have both Automatically accept meeting requests and process cancellations and Automatically decline conflicting meeting requests settings checked in Resource Scheduling...

Am I missing something that would allow it to automatically send notifications when the actual calendar is not online and connected to exchange through outlook?



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