Adding iCloud Account to Outlook for Mac Fails

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Adding iCloud Account to Outlook for Mac Fails

In attempting sync contacts by adding my iCloud account to Outlook for Mac on my new MacBook Air 15, Tahoe 26.3, my password fails every time I did the app-specific password thing, but it also fails. I started this process by adding account, using my personal email as user id (which works for Apple), and then trying my Apple login. Fail. Set an app password, it also fails. I just signed in to iCloud.com on the web using my Apple password, but the app password fails there as well.

Looking for the tip I am missing. Thanks, Bruce

Posted on Feb 18, 2026 2:09 PM

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Answer 1

navygrad Author

Level 1

4 points

Feb 18, 2026 3:02 PM in response to navygrad

Further on this, I switched Outlook for Mac from "legacy" to "new" version, and was able to sign in to iCloud and almost got set up. Seems you MUST use an iCloud email address, which I so far don't have. On to the next step. Will update once I try that.

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Answer 2

Feb 18, 2026 9:58 PM in response to navygrad

navygrad wrote:

Now to figure out how to get the "on my computer" contacts to sync with iCloud so they are available on an iPhone!

I sometimes have to disable, then re-enable some iCloud setting (Safari Bookmarks Reading list, etc) before it syncs to other devices (sometimes I do that in both devices so the info is merged). If that fails, try to logout from iCloud, reboot, and log back in.

But (just in case) backup before doing that. Or additionally backup the Contacts:

https://discussions.apple.com/thread/255488770?answerId=260200973022&sortBy=oldest_first#260200973022

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Answer 3

navygrad Author

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4 points

Feb 18, 2026 4:36 PM in response to navygrad

OK, set up an iCloud email and was successful in adding that to Outlook for Mac. Now to figure out how to get the "on my computer" contacts to sync with iCloud so they are available on an iPhone! Anyone got a trick?

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Answer 4

navygrad Author

Level 1

4 points

Feb 19, 2026 10:52 AM in response to navygrad

Well, I've got numerous accounts included in Outlook for Mac now, my main email account, Outlook.com account, school account, and iCloud account. And I have been able to add contacts and have them sync to my iPhone, from a couple of these. Not sure exactly what I did, but as long as I have one that works, I'm happy. Oh, and I found a pull down item to the right of each contact list titled "sync," and that seemed to do the trick.

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