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We been getting many reports of this as of late, but it appears it has been going on for months.
When a user creates or accepts a meeting request that overlaps another, longer meeting, it only shows the shorter of the two in Outlook. However, it shows both meetings fine using the web client.
Is there a setting for this anywhere that I am missing?
Define overlap - does the longer meeting completely encompass the shorter one, or just the end of a shorter meeting run into the start of a longer one?
Bugzilla
Wiki
Source
Overplapping Appointments missing 
Linear Mode
