“Problem with the Outlook 365 calendar in window 11

Mondo Lo Papa 0 Reputation points
2026-08-07T18:23:28.8333333+00:00

After syncing my contacts and calendar from iCloud, my reminders stopped working

Outlook | Windows | Classic Outlook for Windows | For home
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  1. Victor1-V 11,680 Reputation points Microsoft External Staff Moderator
    2026-08-08T07:19:29.5+00:00

    Hi Mondo Lo Papa,

    Thank you for explaining that the reminders stopped after you synchronized your iCloud contacts and calendar. Please note that this is a user-to-user forum, so contributors cannot access your Outlook or iCloud configuration directly.

    The Q&A Assist answer contains some appropriate initial checks, particularly verifying that Show reminders is enabled in Classic Outlook. Have you had a chance to try those steps, and did anything change?

    I would also like to add the following check without repeating the earlier suggestions:

    1. Open an affected iCloud appointment and confirm that a reminder time, such as 15 minutes, is still selected.
    2. Create a new test appointment directly in the iCloud calendar in Outlook and assign it a reminder a few minutes ahead.
    3. If the reminder is assigned but does not appear, close Outlook.
    4. Press Windows key + R, enter outlook.exe /cleanreminders, and select OK.
    5. Reopen Outlook and test the new appointment again.

    The command rebuilds Outlook’s reminder list and does not delete calendar appointments. For reference, see Calendar reminders in Outlook can't be dismissed or keep reappearing - Exchange | Microsoft Learn

    If the issue continues, please confirm whether reminders fail only for the iCloud calendar or for every calendar in Outlook, and whether new appointments are also affected. This will help distinguish an iCloud synchronization issue from an Outlook reminder-list issue.

    I hope this helps identify where the reminder problem is occurring. 

    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.    

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  2. AI answer

    2026-08-07T18:23:45.35+00:00

    If reminders stopped after the iCloud sync, check both Outlook reminder settings and Windows notification settings.

    1. In classic Outlook, turn reminder pop-ups back on:
      • Go to File > Options > Advanced.
      • In Reminders, make sure Show reminders on top of other windows is checked.
      • This feature is available for Microsoft 365 subscribers on Version 1804 (Build 9226.2114) or higher, and not available for Outlook 2021 or older.
    2. In Windows 11, confirm Outlook notifications are allowed:
      • Open Start > Settings > System > Notifications.
      • Make sure Get notifications from apps and other senders is On.
      • Make sure Do not disturb is Off.
      • Find Outlook in the sender list and make sure notifications are turned on.
    3. Check Windows Focus settings:
      • Go to Start > Settings > System > Focus.
      • If a focus session is running, select Stop focus session.
    4. Check Teams status if Teams is installed:
      • Make sure status is not set to Do not disturb, because that can suppress Outlook notifications.
    5. If the problem started right after iCloud for Windows setup, verify the iCloud integration is still configured correctly:
      • Open iCloud for Windows.
      • Make sure Contacts and Calendars sync is selected, then select Apply.
      • Open Outlook again and test reminders.
    6. If iCloud setup showed an Outlook profile/default profile error, repair the Outlook association:
      • In Windows, go to Start > Settings > Apps > Default apps > Set defaults by app.
      • Select Outlook > Manage.
      • Make sure the listed file types are associated with Outlook.
      • Then run an Office Online Repair and restart the PC.
      • After restart, open iCloud and test sync again.

    If calendar items are present but only reminders are failing, the most likely causes are Windows notification settings, Focus/Do not disturb, or Outlook reminder display settings.

    AI-generated content may be incorrect. Read our transparency notes for more information.

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