How do I speak to an actual human agent to get help with Outlook calendar problems

Question

How do I speak to an actual human agent to get help with Outlook calendar problems

Fergus Macbeth 0

I have a problem with my calendar in classic Outlook which will no longer sync with iCloud. Apparently, iCloud now only syncs with calendar in new Outlook . But one cannot migrate the calendar from classic to new Outlook. I have tried for hours to solve the problem and need to speak to an agent at Microsoft rather than a useless bot who is completely unhelpful and then blocks me.

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Answer 1

Sin-D 4,205 Microsoft External Staff Moderator

Hi Fergus,

Thank you for posting your question in the Microsoft Q&A Forum. I understand that you’re having trouble syncing your New Outlook calendar with Classic Outlook, as well as syncing iCloud with Classic Outlook.

First, go to https://outlook.live.com or https://outlook.office.com and check if your calendar sync works properly. If Outlook on the web works fine, try re-adding your account in both New Outlook and Classic Outlook. If the issue persists, go to Settings > Installed Apps and repair your Outlook/Office installation. For data security, consider creating a backup before troubleshooting.

As a temporary workaround, you can use Outlook on the web and install it as a web app (similar to New Outlook). For instructions, refer to: Use the web version of Outlook like a desktop app

If you still need to contact Microsoft Support:

Go to Contact Support.
Type “Outlook syncing problem” > Scroll down and click Contact Support (skip all troubleshooting steps or similar articles if you just want to contact Microsoft Support).
Sign in if prompted.
Select Products and Services > Microsoft 365 and Office > Outlook.
Choose Chat with a support agent in your web browser.

The initial response might not address the problem. So, if your problem persists or you need any assistance, feel free to ask me by clicking "Add Comment". Thanks for your effort.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Best regards.

Fergus Macbeth 0 Reputation points

2025-10-27T08:20:25.85+00:00

I finally got through to an agent yesterday. That itself is not an easy or obvious process as your answer above shows. After an hour, it seems that there is deep problem with Calendar in Outlook. New Outlook has been released (and we have been encouraged to use it) without it being possible to migrate either the Calendar or Contacts (how daft is that?).

After 4 hours on the line with Apple help agents previously I was told that iCloud no longer syncs with Calendar in classic Outlook only with new Outlook. Microsoft says that their software should still sync between Calendar in classic Outlook and iCloud. In my case it clearly does not. Perhaps the callback today will provide a solution but it looks as though there is a Catch 22 which needs untangling.

Meantime during the whole process I have lost a number of entries from my Calendar. After almost 5 hours of 'help' and several hours trying to sort it myself previously I am worse off than before and my Outlook calendar still cannot sync with my iPhone.
Sin-D 4,205 Reputation points Microsoft External Staff Moderator

2025-10-28T04:28:58.2266667+00:00
Hi Fergus,

Thanks for your response and detailed follow-up. I’ve found some feedback suggesting that re-adding the account can resolve certain syncing issues. You can try the following steps to see if it helps. Please ensure you have set up an app-specific password through Apple, and for data security reasons, consider backing up your data first (especially if you’ve lost some calendar entries).

On your Windows device, go to: Control Panel > User Accounts > Mail (Microsoft Outlook). Then add the account using these settings:

IMAP

Server name: imap.mail.me.com

Encryption: SSL/TLS

Port: 993

Username: your iCloud email address

Password: Apple-generated app-specific password

SMTP

Server name: smtp.mail.me.com

Encryption: STARTTLS

Port: 587 (make sure to change from 465 to 587)

Username: your iCloud email address

Password: the same app-specific password used for the incoming mail server

I look forward to your feedback. Feel free to ask if you have any further questions. Thank you so much.

Best regards.
Sin-D 4,205 Reputation points Microsoft External Staff Moderator

2025-10-29T07:23:14.8766667+00:00

Hi Fergus,

Just checking in one more time to see if the steps resolved the issue. Additionally, I found an article similar to your case. You may consider trying the following steps: iCloud Windows 11 Classic Outlook - Apple Community.

If you still need help, feel free to ask me.

Thanks!
Fergus Macbeth 0 Reputation points

2025-10-29T10:37:24.52+00:00

Thanks. I have resolved the problem. But your answer would not have been entirely helpful as I would not have known what an Apple-generated app-specific password was or how to get it. When you give advice do not assume people understand everything you do.

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How do I speak to an actual human agent to get help with Outlook calendar problems

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