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Microsoft Outlook

Bruce Lawrie 0 Reputation points
2025-12-31T17:40:44.2133333+00:00

main problem is SYCNING: outlook classic calendar no longer goes to iPhone, outlook new will. Neither one goes to iCloud. OUTLOOK new is better than nothing. Been a month not working right. Where is mICROSOFT in all this? Try calling you get no where. Call and say you want to buy more of their products, you can get right through UNTIL YOU say you need help with their product. Frankly I feel mICROSOFT WOULD MAKE A GOOD SWEAR WORD.

Any suggestions ?


Moderator: Moved from System Center Service Manager

Outlook | Outlook for mobile | Outlook for iOS | For home
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  1. Chloe-L 13,665 Reputation points Microsoft External Staff Moderator
    2026-01-01T20:01:11.46+00:00

    Dear Bruce Lawrie,

    Thank you for posting your question to the Microsoft Q&A forum. I understand how frustrating it is when a feature as essential as calendar syncing stops working for over a month, especially when it feels like you cannot get the direct support you need.

    The reason for the situation you are having is a specific technical distinction between the two versions of Outlook:

    • Outlook Classic relies on a local software bridge called "iCloud for Windows" to sync data to your iPhone. If that bridge disconnects or gets "stuck," the sync will stop immediately.
    • The New Outlook is a cloud-based app that operates differently and does not support the "iCloud for Windows" bridge at the moment.

    Here are the specific steps to reset that bridge in Outlook Classic and get your calendar moving again.

    1.Close Outlook Completely

    • Make sure Outlook Classic is not running. Check your taskbar to ensure it is fully closed.

    2.Open "iCloud for Windows"

    • Press your Windows Key on your keyboard.
    • Type "iCloud" and open the iCloud app.

    3.Reset the Connection:

    • Look for the option labeled "Contacts and Calendars" (or "Mail, Contacts, and Calendars" depending on your version).
    • Uncheck the box next to it.
    • Click Apply.
    • Wait about 10-15 seconds.
    • Check the box again and click Apply.
    • The app will now run a setup wizard saying "Downloading calendars..." or "Setting up Outlook."

    When open Outlook Classic, you should see the "iCloud" calendar section reappear in your list, and your appointments should start syncing to your iPhone within a few minutes.

    Regarding the New Outlook:

    Since the New Outlook is in a phase of continual enhancement, you can contribute to bringing better iCloud integration to future updates by providing your input directly via the Feedback Hub. Microsoft actively listens to users to improve their service, so the more a feature is requested, the more likely it is to be prioritized.

    I hope these steps help re-establish the bridge between your PC and your iPhone. Please let me know if these steps resolve the sync issue or if you need specific guidance on how to reach Microsoft live support.


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  2. Bruce Lawrie 0 Reputation points
    2026-01-17T05:10:21.62+00:00
    The computer sync problems and others are fixed, and computer is up and running well.
    On your list, the first three items for sure were tried. As to the rest I am not sure.
    My Son-in-law came in from out of state and three hours later had system up and running.
    His background is primarily Apple, but he also has extensive Windows hands-on experience.
    There was more than just the sync problem. That was the problem, but probably not the cause.
    I doubt anyone without hands on, starting from scratch could have accomplished the repair.
    Three hours later the system was up and running. it will be a week tomorrow.
    
    Ps: I do wish Microsoft had live help for those of us with so very limited computer skills.
        I have always purchased Dell computers in order to purchase their tech help when needed.
        They were stymied also and thought perhaps it was a software upgrade. 
        Thank-you for forwarding your suggestions to me. 
    

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  3. AI answer

    2025-12-31T17:40:52.8066667+00:00

    It seems you're experiencing synchronization issues between Outlook and your iPhone, as well as with iCloud. Here are some suggestions that might help you resolve these issues:

    1. Check Account Settings: Ensure that your Outlook account settings are correctly configured for syncing with your iPhone and iCloud. This includes verifying that the correct account type (IMAP, Exchange, etc.) is being used.
    2. Update Outlook: Make sure you are using the latest version of Outlook. Updates often include bug fixes and improvements that can resolve synchronization issues.
    3. Rebuild the .ost File: If you're using Outlook 2010 or later, consider rebuilding your .ost file. You can do this by deleting the existing .ost file and allowing Outlook to download the information again from the Exchange Server. Make sure to back up any local data first.
    4. Clear Offline Items: For specific folders that are not syncing, you can right-click the folder in Outlook, select Properties, then Clear Offline Items, and finally update the folder.
    5. Use the Inbox Repair Tool: If you suspect there might be corruption in your Outlook data file, you can use the Inbox Repair Tool (Scanpst.exe) to diagnose and repair errors in your .ost file.
    6. Contact Support: If these steps do not resolve the issue, consider reaching out to Microsoft Support for further assistance. While it can be frustrating, they may provide more targeted help for your specific situation.

    These steps should help improve the synchronization between Outlook and your devices.


    References:

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

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