Some reminders not popping up at all

thanks for the review, pls check my response below

1/ Did this behavior also occur in the New Outlook for Mac or in Outlook on the web?  - I only use the desktop version of Outlook, so referring to that only.

2/ When the issue occurs, did you notice any consistent pattern, such as it happening after opening a specific application on the device, immediately after the device starts, or after it has been running for some time? It's different everytime, for ex - after I posted the issue online, number of reminders were 51, and now they are 29, so it appears only the ones that were supposed to pop up today are now showing and everything from Thu, Friday are not appearing now. very strange, not sure what is causing this?

3/ Could you please confirm the version of Legacy Outlook for Mac that you are currently using? I am using Version 16.107.4 (26040410)

Hi Ashish Gupta 

To better understand your situation, may I clarify the following points? 

1/ Did this behavior also occur in the New Outlook for Mac or in Outlook on the web? 

2/ When the issue occurs, did you notice any consistent pattern, such as it happening after opening a specific application on the device, immediately after the device starts, or after it has been running for some time? 

3/ Could you please confirm the version of Legacy Outlook for Mac that you are currently using? 

In the meantime, you may try the general troubleshooting steps below 

• Remove the account and then add it again 
• Remove Outlook for Mac and reinstall it using the version available in the Update history for Office for Mac - Office release notes | Microsoft Learn 

If I’ve misunderstood any part of your situation, or if you have further questions or updates, please don’t hesitate to reply. 

Thank you for your time, and I look forward to hearing from you soon. 

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

For classic Outlook for Mac, intermittent missing reminders are usually caused by reminder settings being disabled or by general Outlook reminder issues.

Check and adjust these areas step by step:

1. Confirm reminders are enabled in Outlook
   In classic Outlook for Windows, reminders can be turned off globally; the same concept applies on Mac via Outlook options. If reminders are disabled, some or all will not appear. In Outlook for Windows the path is:
   • File → Options → Advanced → Reminders → ensure Show reminders is enabled. On Mac, verify the equivalent reminder/notification options in Outlook preferences are turned on.
2. Verify notifications at the OS level
   Even if Outlook is configured correctly, system-level notification features can suppress alerts:
   • Check macOS notification settings for Outlook and ensure alerts/banners and sounds are allowed.
   • Make sure any “Do not disturb” or focus modes in macOS are not blocking Outlook notifications.
3. Check for known reminder issues in Outlook
   Outlook can show errors such as “There was a problem reading one or more of your reminders. Some reminders may not appear.” When this occurs, reminders may fail to fire reliably and other symptoms can appear (for example, issues in the To-Do bar or messages stuck in Outbox). These issues are documented in Outlook troubleshooting guidance and may require profile repair or other remediation.
4. If using shared/delegate calendars
   If some of the missing reminders are for meetings created as a delegate (on behalf of someone else) from mobile or other Outlook clients, be aware of a known issue where delegate-created meetings can show None as the reminder in the owner’s shared calendar. The workaround is to create such meetings using Outlook on the web or the new Outlook for Windows so that reminders are preserved.
5. If reminders are controlled by policy
   In some organizations, reminder behavior is enforced via Group Policy. In that case, reminder options may be greyed out and cannot be changed locally. The underlying setting is stored in the registry on Windows (for example, Type under the Outlook Options\Reminders key). If a similar policy is applied in the Mac environment by IT, contact the organization’s administrator to confirm whether reminder behavior is being centrally managed.

If, after checking Outlook’s own reminder settings, macOS notification settings, and any delegate/shared calendar scenarios, reminders still fail intermittently, escalate through the organization’s IT support so they can review client logs and any applied policies.

References:

• Reminders in Outlook do not appear
• Outlook issues, including reminders that fail to appear, messages stuck in the Outbox, and Desktop Search indexing problems
• No meeting reminders for delegates
• Add or delete notifications or reminders in Outlook
• Mail and calendar notifications in Outlook.com