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CRM 2011 outlook sync of appointments occasionally deletes a bulk of the synced appointments from CRM

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I have a client with the setup and problem described below.
We are still months away from upgrading CRM from 2011 to the newest version.
Due to an integration to another system it is highly business critical that the appointments from the users calendars are synced to CRM.

The setup is

  • CRM 2011 (5.0.9690.4376)
  • Outlook 2016
  • Outlook addin for CRM (5.0.9690.2838)
  • Exchange 2016 connected to exchange online

What we have identified about the problem

  • A user experiencing the problem has a set of appointments that are synced between CRM and Outlook. At some point in time (seems to be random) Outlook sync decides to delete some (not all) of the appointments in CRM but leave them in Outlook. The appointments in question seems to have lost the tracking to CRM, so it is just as if the user has stopped tracking of the appointments with the choice of deleting them in CRM.
  • The problem has been identified for several but not all users
  • The problem has been identified several times for the same user

What we have not been able to establish (yet)

  • A pattern in time
  • A pattern in where the appointment was created (outlook vs CRM)
  • A pattern in who has created the appointment (the user in question or someone inviting the user to an appointment)
  • A pattern in recurring or solitary appointments
  • A trace from the Outlook client over a period where there is an incident of this problem

Has anyone else experienced this problem or something similar?


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