Last Updated: March 1, 2019
This error may occur when you try to send email using an Outlook.com Connected Account:
"This message could not be sent. You do not have the permission to send the message on behalf of the specified user.”
The Outlook Team is investigating a fix. As a workaround, add the Connected Account as an Outlook.com secondary Alias. To do this:
Go to this page https://account.live.com/names/Manage.
Under Account Aliases, click Add Email.
Under Add an alias, click the radio button for Add an existing email address as a Microsoft account alias.
Click the button Add Alias.
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