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Delegates seeing deleted sent items in outbox

I have a strange situation.

We user Exchange 2012 with Outlook 2007 in cached mode. All of our secretaries have Full and Send As access to several Manager's mailboxes.

When a Manager deletes an item in their Sent Items box it appears in the Manager's Outbox on the Secretaries Outlook. It does not appear on the Manager's local Outlook. I hope that makes sense?

There reason for deleting Sent Items is to prevent very private emails internal emails being seen by people who may potentially be effected. Personnel matters, for instance.

This "bug" is essentially just highlighting these emails as they are showing as Unsent Items in bold. I've even had a call logged from a Secretary saying her boss has several emails stuck in his Outbox (which they aren't).

Can anybody shead any light on this place?


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