Hi kevin langston,
Welcome to the Microsoft Q&A forum.
I understand you’re trying to link your iCloud contacts, calendars, and tasks to the new Outlook for Windows, and it’s frustrating when that data does not appear or sync as expected.
To help narrow this down, I’d like to clarify one point first: When you add your iCloud account to the new Outlook, does iCloud Mail appear correctly, but contacts and calendars are missing, or are none of the iCloud items showing at all?
In the meantime, here are some important checks and clarifications based on how the new Outlook currently works:
1, What the new Outlook for Windows supports
In the new Outlook for Windows, iCloud Mail, Calendar, and Contacts are supported through Apple sign-in (OAuth). If you are still being prompted for an app-specific password, please update the Outlook app and restart it, then try adding the iCloud account again. Reference: https://techcommunity.microsoft.com/blog/outlook/it%E2%80%99s-now-easier-to-access-icloud-mail-calendar-and-contacts-in-outlook/4465707
2, Confirm the iCloud account is added inside Outlook
Please go to Settings > Accounts > Email accounts in the new Outlook and confirm that your iCloud account is listed there. Simply signing into Windows with an Apple ID or having iCloud for Windows installed does not automatically connect iCloud data to the new Outlook.
3, Check the sign‑in flow
When adding the iCloud account, Outlook should redirect you to your browser to sign in to your Apple account and grant permission. If you were prompted for an app‑specific password instead, please make sure Outlook is fully updated and restart it before trying again.
4, If you previously used iCloud for Windows
Apple’s iCloud for Windows instructions focus on syncing Calendars and Contacts into the classic Outlook experience. If you previously used that method, it may not behave the same way in the new Outlook, so adding the iCloud account directly in the new Outlook is the key step.
Reference: https://support.apple.com/guide/icloud-windows/calendars-and-contacts-icwa12798053/icloud
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5, Verify the data exists in iCloud
Please also confirm that your contacts and calendars are visible at iCloud.com, and that you are using the same Apple account everywhere. If the data is missing there, Outlook will not be able to display it.
Please note that this is a public community forum, and contributors here do not have access to account‑level sync logs or Apple account details. However, once you confirm whether mail is syncing and which items are missing, we can better determine whether this is a configuration issue.
I hope this helps.
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