Calendar Update/Syncing Issue

Question

Pretext - Hybrid Exchange environment

Microsoft® Outlook® for Microsoft 365 MSO (Version 2202 Build 16.0.14931.20272) 64-bit

Windows 10 Enterprise

We have two executive assistants in our org that are experiencing issues when making updates or changes to their shared calendars on Outlook (i.e. pertaining to the executives they support), the users have full permissions to these shared calendars. Below are some examples as to what the current issues are:

• Scenario 1 (Disappearing Meetings): Executive Assistant forwards a meeting invite to UserA (admin has full access to UserA calendar) - UserA accepts the invite. But when Executive Assistant is viewing User A's calendar post User A accepting the meeting invite, Executive Assistant does not see the meeting on UserA shared calendar on her Outlook. Happens with in all these item types, a meeting request, a recurring meeting, an updated meeting request and a standalone appointment?
• Scenario 2 (No Change): Executive Assistant has several shared calendars attached to her Outlook. When she updates/modifies any of those calendar meetings either on the behalf of UserA, UserB and so on...the recipients on XYZ meeting do not see these updates / changes - nor does the updated Calendar item reflect on UserA, UserB etc... Calendars on their Outlook - or the shared Calendar on Executive Assistant's Outlook.
• Scenario 3 (Duplicate Meetings): Executive Assistant will make a change on existing meeting on behalf of UserA and will result in a duplicate meeting on recipient's side. Verified that this shows up locally on Outlook app and also outlook.com.

Other things to note with these sync discrepancies:

1. Verified that these discrepancies are visible on outlook.com
2. Some meetings appear 2x on UserA, UserB side
3. Meeting Disappear from Outlook, in which they have to be recreated.
4. Conflict message will appear in Scenario 2, if meeting is then deleted recipient will still have meeting appear on calendar.

Answer 1

Hello ChrisJP_45,

If you got any furhter updates, welcome to share with me, thanks.

Best Regards,

Oliver

Answer 2

Hello ChrisJP_45,

I am glad to help you here. According to the scenarios you shared above, the assitant have delegate permissions to different users and the calendar items ( created or modified) not updated in the users' calendars, and some time it would cause duplicated items in the users calendar, please clarify if I misunderstand your scneario, thanks.

If so, since you have Exchange Hybrid environment, first may I double confirm if the assistant (mailbox) and your users mailboxes (A, B, C...) are hosting on-premises Exchange or Exchange Online now? And I noticed all the scenarios you mentioned above are related to the delegate assistants, in this time, please sugges your users directly perform some tests ( like create or update meetings) without the assistant interrupting and then see if it has the same issue.

To further troubleshooting, I'd like to collect some more info as below

1, the assistant (mailbox) and your users mailboxes (A, B, C...) are hosting on-premises Exchange or Exchange Online ?

2, when the assitant updates meeting details, he cannot see the updates from the shared clanedar, if the owner ( your users A, B, C) could see the updates on their side with a refresh or re-login?

3, if the users got same issue when they perform tests without delegate assistants?

Best Regards,

Oliver