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Appointments in Outlook not tracking to CRM - after New Year

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I have a user that had successfully created appointments on his Outlook calendar and used set regarding or track in CRM and they subsequently showed up in My Activites in CRM. The last one that synced was from 12/28/2016.   However since the New Year (1/1/2017) it appears that functionality isn't working for him, none of the appointments he's tracked are showing up in CRM, but it is for other users.   We have Dynamics CRM 2016 On-Premises and this user has the Outlook Client installed.

I checked his View filters for My Activities and the synchronization settings for Appointments in Options in CRM which appear to still be default. His roles are same as others who are not having issues.   When going into the appointment in the Outlook Calendar for an appointment in 2017 that he tracked you definitely see the link to CRM at the bottom where it says what its tracking to.   Yet its just not in CRM, tried Advanced Find query with no filter for all Appointments...  I'm perplexed, any ideas?


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