Learn what to do if Outlook 2010 repeatedly asks you to authenticate your iCloud account and won't completely open. If there's a password pre-populated for you, you might need to update it with an app-specific password.
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To open Outlook 2010 with two-step verification, you must generate and use an app-specific password:
Click Generate Password and follow the steps on your screen
In the Internet E-mail authentication prompt, enter the app-specific password that you generated.
Select “Save this password in your password list” to allow Outlook to automatically authenticate your password each time. If you want to enter your app-specific password manually each time you open Outlook, skip this step.
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