You have to be careful with hosted Exchange (i.e. Office 365) as it is
picky about the 'from' address exactly matching valid credentials. The
following works for me:

Port = 587
Use SSL = true
Authentication = a valid username and password for an account that can
send  ("bi...@yourdomain.com", "billypassword")
IMPORTANT GOTCHA: The 'From' address must exactly match the
authentication address ("bi...@yourdomain.com") otherwise you will get
"5.7.1 Client does not have permissions to send as this sender"


Also be aware that there are recipient and send rate limits with Office
365 hosted Exchange, so a maximum number of recipients you can send to
per hour, and a maximum number of messages, and a maximum rate of
submission. This is to stop people using it for bulk mailing. If you
need to do that, you should really by using a dedicated service like
MailJet (which can send on behalf of your domain).

Those rates only apply to submitting via SMTP. If you submit messages
through Outlook via some automation method, or to Office 365 using one
of the web APIs, internal queuing and throttling will be performed so
that you don't hit those limits.


-- 
  Alan Bourke
  alanpbourke (at) fastmail (dot) fm

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