Delegate tracking of contacts and appointments does not work with server-side synchronization or with the new Dynamics 365 Outlook app.
Consider the scenario where the company owner, Ms. Bigwig, wants her appointments and contacts tracked in CRM, but she is too busy to maintain her calendar herself, so she has her assistant add items to her calendar and contacts and then track them in CRM.
According to the official documentation, “If you’ve delegated access to your Outlook account, the delegate can track items on your behalf.” So delegate tracking is possible. However, what the documentation (currently) does not state is that delegates tracking contacts and appointments on your calendar will not work if your mailbox uses server side synchronization or if you or the delegate are using the new Outlook app.
For delegates to track items on your calendar, you must be using Outlook synchronization for contacts, appointments, and tasks. In the scenario of Ms. Bigwig, she can have her assistant track things in her mailbox, but these items will not synchronize to CRM until Ms. Bigwig logs into Outlook. If she travels and does not open Outlook for two weeks, the delegate tracked items won’t appear in CRM until the next time she opens Outlook.
So if you want to use server side synchronization and you want delegates creating or updating Outlook items, an alternative approach to delegate tracking is to have the assistants create items directly in CRM and assign them to Ms. Bigwig. These items will then synchronize to the boss’ calendar immediately via server-side synchronization.