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Mailbox forwarding: Meeting invites not showing on both calendars

Andre LeBlanc 1 Reputation point
2022-04-07T16:22:15.697+00:00

Due to a recent Merger & Acquisition ("M&A"), our employees currently have to monitor two mailboxes (including the respective calendars), each residing on their respective Exchange Online servers. We have Outlook desktop client showing both mailboxes (on the separate Exchange envs).
For the respective mailbox items, I'll prefix it with Legacy* and New*.

Until we merge our Exchange environments, I am currently recommending users setup forwarding from LegacyMailbox to NewMailbox, with the option to
not keep the original email in the LegacyMailbox.
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The reason for NOT keeping a copy of the email is so that there is less confusion in having two inboxes. The user can effectively just monitor their NewInbox. Additionally, when the merging of mailboxes does take place, there won't be duplicate emails. Not keeping a copy creates a very clear cutoff date of stuff going into the LegacyInbox.
OK, so far so good.
This next part is where the inconsistency happens.

When User_1 receives a meeting invite to their LegacyMailbox, you can see the meeting invite populate in their LegacyCalendar (as an unaccepted meeting / placeholder). After a few moments, we will then see the meeting invite populate in LegacyUser_1's NewCalendar.
This is ideal as it helps keep the calendars somewhat synchronized, if only from a visual standpoint.

When User_2 receives a meeting invite to the LegacyMailbox, the meeting invite is not showing up in their LegacyCalendar. As expected, it is being forwarded to their NewMailbox and showing up in the NewCalendar.

So what's up with this inconsistency? Everyone in this pool is an E5 license holder. I have a number of people where they are experiencing User_1, and I have plenty of others that are experiencing User_2.

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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Microsoft Exchange Online Management
Microsoft Exchange Online Management
Microsoft Exchange Online: A Microsoft email and calendaring hosted service.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Andre LeBlanc 1 Reputation point
    2022-04-11T13:55:24.887+00:00

    @ChristyZhang-MSFT Thank you for updating the tag.

    @Joyce Shen - MSFT All users set their Forwarding using the option in OWA. "Keep a copy of forwarded messages" is not enabled.

    When LegacyUser_1 receives a meeting invite, it shows up in their LegacyCalendar and in their NewCalendar.
    When LegacyUser_2 receives a meeting invite, it only shows up in the NewCalendar.

    Across our global enterprise, I believe we may have more people getting the experience of User_1 (where the invite shows up in both calendars).

    If it would help, I can supply a video showing the experience of User_1 and User_2.

    Should I consider opening a Service Request in my Office 365 Admin Center?