* You only need to use an app-specific password if you’re manually setting up mail with your iCloud account in Windows, if you use Mac OS X Mail (10.7.4 and earlier), or if you use any other third-party mail client. Since Outlook is a third-party mail client, you'll need to have two factor authentication set up for your Apple ID in order to generate the app-specific password mentioned above: Two-factor authentication for Apple ID Mail server settings for iCloud email clients
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