Special tricks to add iCloud accounts into Outlook 365 for Mac

iCloud accounts can now be added to the new look Outlook 365 for Mac but there are limitations and it’s harder than Microsoft’s ‘help’ says.

Outlook for Mac has always been able to link with iCloud using IMAP.  Now Outlook 365 for Mac with the new interface can automatically setup a synchronization with iCloud account.

As Microsoft tells it, all you have to do is add an account, give the email address and password and Outlook will handle the rest.

It’s not that simple.

Most iCloud accounts have two-factor authentication. Apple encourages ‘two fac’ for better account security. With ‘two fac’ it’s not enough to enter your regular iCloud password when Outlook asks for it.

A special ‘app specific password’ is needed.

Get App Specific Password for iCloud account

An app specific password is a special ‘one off’ password that lets a program access your account without two-factor authentication.  Both Apple and Microsoft have app password options to let older software work in the modern ‘two factor login’ world.

Go to https://appleid.apple.com/account/manage you’ll have to login with a two-factor code to access your account.

On the Manage page, under Security | App-Specific Passwords, choose Generate Password.

Type in a name or label for the app-specific password.  That’s so you know what the password is for at some later time (there’s a list of app-specific passwords in the Manage | Security section).

Click Create to see the special password.

Copy that password and paste into Outlook 365.  Click Add Account and Outlook should create the account.

How iCloud is connected to Outlook

Outlook uses IMAP to sync your iCloud mailbox to Outlook.

No Calendar, No Contacts

That means only email is synced between iCloud’s online mailbox and Outlook for Mac.

There’s NO calendar or contacts support between iCloud and Outlook for Mac or Windows.  That’s because IMAP is limited to email folders.  iCloud doesn’t support Microsoft’s Activesync which syncs all folders, including calendar and contacts.

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