Bookings meetings sync with iPhone, but not with MacBook

Question

tl;dr — I have an issue where Microsoft Bookings reservations are synced from my institutional email address to Apple Calendar on my iPhone, but not to Apple Calendar on my Mac. This is extremely annoying.

Hardware and software

I have a 2019 Intel MacBook Pro running macOS Ventura 13.2.1 and an iPhone 13 running iOS 16.3.1. I use Spark as my email client and Apple Calendar as my calendar client, on both my Mac and my iPhone.

The problem

Through my institutional Microsoft Outlook email, I use Microsoft Bookings to schedule short meetings with my students. I'm notified via email whenever someone makes a reservation. These Bookings meetings show up on my online Outlook calendar and on my iPhone's Apple Calendar, but they do not show up on my MacBook's Apple Calendar. Bookings meetings are sent to my default "Calendar" calendar on Outlook and cannot be sent to a different calendar (at least based on my attempts!) — the Outlook default "Calendar" is synced with both my iPhone and MacBook. (While writing this, I got a Calendar notification for an upcoming meeting on my iPhone, but not on my MacBook! I don't want to miss meetings because I don't have my phone on me.)

What I've tried

I've tried enabling/disabling the default "Calendar" calendar on Outlook, enabling/disabling my institutional email on my MacBook, signing in/out of my institutional email address on my MacBook, and gone through many many pages of Outlook settings. This page won't let me upload images (they keep failing, not sure why), but I have the appropriate calendars selected in all three locations.

Any help would be greatly appreciated — this issue has been bugging me for months!

Answer 1

I just noticed this problem when I changed how I was using bookings (this may be a work around, see below). I had created and have been using a "shared bookings page" calendar in Bookings that needed to be assigned to staff (which is just me). It is a calendar for "Student Meetings", with the various types of meetings as "services". I recently learned that I could set up a "personal" booking back (now called "Bookings With Me") and thought I'd try that in an attempt to simplify and eliminate the "staff" option. Turns out that meetings scheduled through the original "shared" calendar show up on BOTH my iPhone and MacBook, while the newer bookings made through the "personal" bookings page aren't showing up.

So, try creating your Bookings page as a "shared" bookings page. It adds a few more elements as far as services, staff, etc, which I more or less ignore and don't seem to cause any confusion for students. If you have different types of meetings those are your "services" and you just assign yourself as the default staff for the service. That's what I'll be going to back to for the time being! I hope that helps!

Answer 2

Here is the summary of what works from the suggestions so far (based on my controlled trials):

1. Creating bookings through "Microsoft Bookings" instead of "Personal book with me" page as suggested by Justin Carrier:

Turns out that meetings scheduled through the original "shared" calendar show up on BOTH my iPhone and MacBook, while the newer bookings made through the "personal" bookings page aren't showing up.

Yes, it works! To clarify what these are, Microsoft Bookings is an individual (calendar with an inbox) app: https://www.microsoft.com/en-us/microsoft-365/business/scheduling-and-booking-app, while "Book with me" is a link on your Outlook calendar.

Bookings app provides a separate email and calendar so that you can identify several people or only yourself as "staff" whose calendars sync and availabilities show up. However, the setup is a little more complicated than the "Book with me". You need to identify your availability under the "default scheduling policy" tab. Also, clients should choose you as the staff they want to meet, even though there is no other option.

In my trial, the appointment through Bookings synced with all Fantastical, iPhone, Mac, and iPad calendars. - ordered based on the speed of synchronization, Fantastical synced first, yet the rest was only 1 min delay.
Again, the appointment through "Book with me" did not show up neither on my Mac nor Fantastical, but did on iOS.

In short, the main problem with Microsoft Outlook Book with me has not been solved for at least a year. This is not an Apple problem because it does work with iOS, not macOS, particularly after the recent MacOS changes after M1. Microsoft has not addressed the issue, still!!!

2. "Subscription" to the Outlook Cal on Apple Cal, instead of adding it as an account:

Interestingly, yes, it works! It is slow - with a 5 min or so delay, but it shows up both Bookings and Book With Me appointments. Yet, I do not recommend the subscription as the only Outlook source because it does not show the preference to accept "invited events". If you have an invitation for the ugly sweater party of the freshmen student society through the bulk email, the subscribed calendar does not provide the option to decline any invitation and shows the events on your calendar, as you accepted it.

Conclusion: I hate Microsoft - disappearing notes in OneNote, disaster random signing off OneDrive, horrible "focus" inbox of Outlook, frustrating unsynced calendar, traumatizing figure embedding of Word, nightmare stuck of videos on Powerpoint. Yes, we are scholars, engineers, etc. and always find workarounds. If Microsoft does its job, we might find more time to do our jobs instead.

Answer 3

Dear Anthony,

It seems like the issue is with the synchronization of your institutional Microsoft Outlook email with your MacBook's Apple Calendar. Here are a few suggestions you could try:

Check your calendar settings: Make sure that your MacBook's Apple Calendar is set to sync with your institutional Microsoft Outlook email. Open Apple Calendar on your MacBook, go to Preferences > Accounts > your institutional email > Account Information > Refresh Calendars. Check that the "Refresh Calendars" box is checked and the frequency is set to your preference.

Check your internet connection: Ensure that your MacBook has a stable internet connection. If the internet connection is poor, it might cause syncing issues.

Update your software: Ensure that both your MacBook and iPhone are running on the latest software updates. Software updates often fix syncing issues.

Check if you have any conflicting settings: Sometimes, if you have conflicting calendar settings, it can cause issues with syncing. Check if you have any third-party calendar apps installed on your MacBook that might be conflicting with the Apple Calendar.

Try adding your institutional email account as a separate account on your MacBook: Try adding your institutional email account as a separate account on your MacBook's Apple Mail app. This could help in ensuring that the calendar events sync properly.

As shown here: https://learn.microsoft.com/en-us/microsoft-365.... Bookings integrates with Outlook to optimize your staff’s calendar. It’s possible that your MacBook’s Apple Calendar is not synchronized with Outlook properly. You may want to check if your Exchange account is added and enabled on your MacBook’s Calendar app. (there is a discussion similar to your problem on Apple's Community: https://discussions.apple.com/thread/253787531 *) You may also want to contact Apple support: https://support.apple.com/en-ca/guide/calendar/...*

I would also refer you to the response of a Moderator of this forum. Qian Zhang, here: https://answers.microsoft.com/en-us/msoffice/fo....

Note: This is a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it.

Best Regards,

George A.

Answer 4

I have exactly the same issue.

Interestingly it also doesn't work with Fantastical on macOS.

Answer 5

I have the same issue. Please help. Tried deleting accounts and set them up again. Nothing seems to work.