Not receiving Reminders via Email from Outlook (web browser) calendar events

Matt from New Glarus 0 Reputation points
2026-10-26T01:02:46.7633333+00:00

I am not receiving my old calendar event reminders anymore. It's like the existing ones stopped sending me reminder emails even though they are all marked to send me an email 15 minutes before and sometimes I have them set up to send 2 emails. It randomly stopped in October so I've missed some events without the email reminders. What gives Microsoft?

Outlook | Web | Outlook.com | Calendar
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  1. Jhun Buala 6,390 Reputation points Independent Advisor
    2026-10-28T01:40:48.4833333+00:00

    Hi,

    It's nice that new event sent its reminder correctly, your Outlook email reminders are still working. The problem seems to be with at least some of your existing calendar events, although we can't say for sure why they've stopped.

    Let's try a few testings on 1 of your existing events.

    1. Open an upcoming event that you're worried about in Outlook Calendar.
    2. Change its reminder from 15 minutes to a different time, then save it.
    3. Open the same event again and set the reminder back to 15 minutes. Save it once more.

    Let's wait for that event's reminder and see if it arrives. If it does, try the same approach with other important upcoming events first.

    Jhun

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  2. Jhun Buala 6,390 Reputation points Independent Advisor
    2026-10-26T03:22:28.28+00:00

    Hi Matt,

    Good day. Let's do some checking first whether the problem affects all reminders or only older events.

    1. Test with a new calendar event. In Outlook on the web, create a test event and set an email reminder for 15 minutes before. Check whether the email arrives. This helps determine whether the issue is limited to existing events.
    2. Check your Outlook rules and Junk Email folder. Go to Settings > Mail > Rules and see if any rule is moving or deleting reminder emails. Also check Junk Email.
    3. Check your calendar notification settings. Open Outlook on the web, go to Settings > Calendar, and review the available event and reminder settings. The options may vary depending on your Outlook account.

    If the new event sends its reminder but older events don't, that points to a possible issue with how the existing reminders are being processed rather than a general email delivery problem.

    Regards,
    Jhun

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  3. AI answer

    2026-10-26T01:03:58.4266667+00:00

    Submit this through Outlook.com’s in-app support because Microsoft’s public known-issues page does not identify an October incident matching existing events that stopped sending reminder emails.^1^

    Open an Outlook.com support case

    1. Sign in to the affected Outlook.com account in the browser.
    2. Select Help on the Outlook.com menu bar.
    3. Describe the issue and complete the suggested self-help prompts.
    4. Scroll to Still need help?, select Yes, and submit the case. This is Microsoft’s documented escalation route for Outlook.com account-specific problems.^2^

    Include:

    • The approximate date in October when delivery stopped.
    • One affected event’s subject, date/time, time zone, and whether it is recurring.
    • A screenshot showing the event’s email-reminder settings, with personal information hidden.
    • Whether ordinary email still arrives normally.
    • Whether the missing reminders appear in Junk Email, Deleted Items, or search results.
    • Whether reminders fail for every event or only older/recurring events.

    Do not delete or recreate an important recurring series before support investigates it; changing the series may remove evidence of its saved reminder configuration.

    Run one controlled comparison

    Create a temporary event using the same email-reminder option, scheduled far enough ahead to configure and observe it. Record whether:

    1. The reminder email arrives.
    2. Any browser notification appears.
    3. The event still shows the configured reminder after saving and reopening it.

    This test only distinguishes newly created events from existing events. A successful browser notification does not prove that the separate email-reminder delivery path is working.

    Important product distinction

    Microsoft’s current reminder article documents popup reminder settings for Outlook on the web used with work or school accounts, including Settings → General → Notifications → Calendar. It does not establish the behavior of per-event reminder emails for a consumer Outlook.com account.^3^

    Therefore, the available documentation does not confirm that the email option was retired, nor does it provide a repair procedure for this specific Outlook.com symptom. Support needs to confirm whether the saved reminders on the account are still eligible for email delivery and whether an account-side service issue affected the existing events.

    References

    1. Fixes or workarounds for recent issues on Outlook.com
    2. Known issues with shared calendars in Outlook | Microsoft Support
    3. Add or delete notifications or reminders in Outlook
    AI-generated content may be incorrect. Read our transparency notes for more information.

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