Before setting up Hotmail/Outlook/Live email in communicator you need to set up an app password. This password will be used instead of your login password. Please follow the directions in this link to set up your app password. https://support.microsoft.com/en-us/help/12409/microsoft-account-app-passwords-and-two-step-verification
Now you can set up your email in Communicator:
- Select the Email pageset on the home page in Communicator 5.
- Select Settings on the top right of the Email page. Select Yes to the warning.
- An Email Settings dialog box will appear. Select New. A New Account dialog box will appear.
- Select Hotmail, Outlook, Live.
- Select Next.
- Enter your name. (You can use the tab key to jump to the next field).
- Enter your email address in the E-mail box.
- Enter your password in the Password box (the one you created as your app password).
- Select Finish then choose OK.
Now when you select Send/Receive your emails will begin to download. If you have more than 200 emails in your Inbox you may need to select Send/Receive multiple times before all the emails get downloaded.