Outlook problem syncing with Icloud Calendar, Outlook shows "Wrong Password" icon in heading

Question

Syncing between my Outlook calendar and Icloud calendar on my Iphone has worked forever but recently the two calendars aren't syncing and Outlook shows a "Wrong Password" icon. I have no idea what password is wrong. I am logged into my Outlook email account and it syncs with the Mail app on my phone (not Icloud mail) just fine, but calendar events stopped working about a week ago and the "Wrong Password" icon appeared on Outlook

I'm using Microsoft Home and Business 2021, version 2510

Answer 1

It sounds like you are experiencing a password-related issue with syncing your Outlook calendar and iCloud calendar. Here are a few steps you can take to troubleshoot this issue:

1. Check Your iCloud Account Settings: Ensure that your iCloud account is set up correctly in Outlook. You may need to re-enter your iCloud password in the account settings.
2. Update Passwords: If you have recently changed your iCloud password, make sure to update it in Outlook as well. You can do this by going to the account settings in Outlook and updating the password for your iCloud account.
3. Enable Two-Factor Authentication: If you have two-factor authentication enabled for your iCloud account, you may need to generate an app-specific password for Outlook. This can be done through your Apple ID account page.
4. Remove and Re-add the iCloud Account: If the problem persists, consider removing the iCloud account from Outlook and then re-adding it. This can sometimes resolve sync issues.
5. Check for Updates: Ensure that your version of Outlook is up to date. Sometimes, updates can fix bugs related to account syncing.

If these steps do not resolve the issue, you may want to consult additional resources or support for more specific guidance.

---

References:

• Outlook continually prompts for your password when you try to connect to Microsoft 365
• Password prompt at every Outlook start or can't create profile

Answer 2

Hi Bigdaddy,

Thank you for sharing your question. I understand you reaching out about the issue you're experiencing with syncing your iCloud Calendar in Outlook. Let’s sort this together.

It's likely that the “Wrong Password” icon you're seeing in Outlook is related to a recent change in how iCloud handles authentication, particularly if you're using Microsoft Office Home and Business 2021 (version 2510). This issue often arises when two-factor authentication (2FA) is enabled on your Apple ID, which requires an app-specific password for third-party apps like Outlook to access iCloud services.

To resolve this, you can try the following steps based on my knowledge.

First, ensure your iCloud account is correctly configured in Outlook. If you've recently changed your Apple ID password, update it in Outlook’s account settings. If 2FA is enabled, you’ll need to generate an app-specific password from your Apple ID account page. Use this password in Outlook instead of your regular Apple ID password.

If the issue persists, consider removing and re-adding your iCloud account in Outlook. This can help reset the connection and clear any cached credentials that might be causing the error. Also, make sure both Outlook and iCloud for Windows are updated to their latest versions, as updates often include important fixes for syncing issues.

May I ask if you’ve recently changed your Apple ID password or enabled two-factor authentication? Also, are you using the iCloud for Windows app to sync your calendar with Outlook?

Feel free to follow up if you need help generating an app-specific password or walking through any of the steps. I'm here to help!

 

Best Regards,

Noel