Troubleshooting Delegate Access to Private Items

[KerryLambert]

Should a delegate have access to view the details of Private calendar items in Outlook for Windows 2016?

Scenario:  Admin Assistant is a Delegate to her manager's calendar.  She can view details of Private entries in Outlook on the Web, but NOT Outlook for Windows 2016.  All she sees is "Private Appointment", no details.

Troubleshooting Steps:

Verified via Powershell "Get-MailboxFolderPermission identity:\calendar" that user has Editor rights

Verified via Outlook on the Web that the user is configured as a Delegate with "Let delegate view private events" checked.

I have also given the delegate FullAccess to the mailbox and she still cannot see the details of Private calendar events.

What could I be missing?

[#2]

Try recreating the Outlook profile or simply test on another machine?

Also, is this for Calendar items only? For those, the permissions on the Calendar folder also matter, see for example this article: https://support.microsoft.com/en-sg/help/2782490/calendar-items-are-not-visible-for-a-shared-calenda...

[#3]

Yes we've tested on another machine and recreated the Outlook profile.  Will try a reimage next.

[#4]

Hello, i have a user (email address removed for privacy reasons) who can view the private appointments of another user (email address removed for privacy reasons) even though he does not have permissions.

I have tried adding him and removing him but that didnt fix it.

Any idea why he can see her private calendar items and how to remove them

@KerryLambert 

@VasilMichev