Recurring meetings won't send from Calendar connected to local Exchange server

My Mac Calendar is connected to my company's local Exchange server. I can create meeting entries in the Calendar and invite others to join. When I do so, the invitation is successfully sent (and it appears as a sent item in my Outlook email client).


HOWEVER, if I create a weekly recurring meeting and invite the same people, when I press send, nothing is sent, and my email 'sent' box shows no indication of the invitation going out. Invitees do not receive it.


Environment: MacOS Ventura, Calendar 13.0, and MS Outlook Mac 16.76.2.


Important notes:

• This behaviour has been independently verified on a colleague's Mac running Ventura. It's only recurring meetings that show the problem.

• There is no error message associated with the failure to send.

• Recurring meetings sent from MS Outlook for Mac's built-in Calendar do not have the problem.


I'd appreciate any confirmation others can make or solutions you can offer.


Mark

MacBook Pro (M2 Pro, 2023)

Posted on Aug 30, 2023 10:21 AM

Reply
5 replies

Aug 31, 2023 10:13 AM in response to Scirius

Hello Mark,


To start out, please make sure you are following these steps to set up that event on your Mac Calendar: Set up or delete a repeating event in Calendar on Mac - Apple Support. It sounds like these are the steps you are taking since you mentioned it works as expected on the built-in Calendar app, but just not through Outlook.


In order to provide the quickest and most efficient resolution, we'd advise that you reach out to the Outlook support team for direct help with their product as they will be the experts on it. This article may offer a starting point: Microsoft - Contact Us.


We hope this helps. Let us know if we can assist with anything else at all. Take care.


Aug 31, 2023 11:16 AM in response to Gena_D

Hi Gena_D


Thank you for your response. I think there is a misunderstanding, though.


Sending repeating meetings works fine when using MS Outlook Mac 16.76.2's built-in calendar.


I don't use Outlook's calendar.


I use Apple's Calendar application (Currently 13.0). From Apple's Calendar, connected to my corporate Exchange server, I can send and receive meeting invitations with no problem, except if I send a meeting invitation that has a weekly recurrence. In this case, the invitation does not send. The problem is replicated on a colleague's MacBook Pro (Apple Silicon). The lack of sent invitations can be confirmed by examining my email sent-mail folder. One-off invitations are present there as sent items. Invitations to recurring meetings simply never send, and do not appear in the sent-mail folder.


I hope others with an in-house Exchange server can test to see if the same behaviour occurs on their Ventura OS Macs using Apple's Calendar app.


I should add that this behaviour is relatively new. I've not had the problem until the last several days or weeks, so it probably affects a fairly recent software update.


I appreciate the help!

Mark



Aug 31, 2023 3:36 PM in response to Scirius

Can non-Microsoft accounts send recurring meeting invites properly? Is your device enrolled in a Mobile Device Management (MDM) platform for your company? If non-Microsoft accounts can send fine, then the issue does lie within Microsoft's stack. If they cannot send fine and the device is managed, try on a non-managed device. If this is successful, then the issue lies with your IT department and policies they may have set.


I am running a managed device and have no issues sending recurring invites with either Google Calendar or iCloud. I don't have a Microsoft account, so I can't confirm the behavior on my machine.

Sep 1, 2023 10:14 AM in response to celliott147

celliott147 wrote:

Can non-Microsoft accounts send recurring meeting invites properly?

Yes, they can. I can send via gmail with no problem. This includes all invitations regardless of recurrence.


Is your device enrolled in a Mobile Device Management (MDM) platform for your company?

No, it is not


I now have some additional information that I think thickens the plot.


I assumed until now that this was a problem with repeating meetings. Now I've done the test. Single meetings, daily meetings, and monthly meetings all are sent without problem. Weekly meetings don't send. This problem is exclusively limited to weekly meetings.


I've now tried this on three MacBooks (Apple Silicon) on Ventura 13.5.1 -- I updated since my original report. The in-house exchange server is Exchange 2013.


It is hard to believe, since these invitations go out essentially as emails, and since every kind of invitation is sent without problems except for weekly meeting invitations, that Mac Calendar is not to blame. The issue is not even on the 'receipt' of these messages; it is clear from looking at the sent-mail box that they never even leave the Calendar app.


Thank you for your response!

Recurring meetings won't send from Calendar connected to local Exchange server

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