Yesterday and today, I grappled with the issue of sending e-mail from an Office 365 account from .NET's SmtpClient. Even though I had provided the correct username/password (I was able to log in manually) and the right host/port (I got them directly from the Outlook Online connection info page), sending messages always failed with an error about an unauthenticated FROM. EnableSsl was, well, enabled, so I was very confused about the authentication error.
It turns out that Office 365 mail servers have a Service Principal Name that must be specified in the TargetName property of the SmtpClient. Specifying that option solved the problem.
client.TargetName = "STARTTLS/smtp.office365.com"
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