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There is a lot of information in rails about setting up rails to work with gmail and I have done this for a personal (e.g. myemail@gmail.com ) website.
Now unfortunately google apps for businesses no longer offers free mail hosting but as it says here apparently outlook do.
so I followed the instructions, changed my DNS MX records and everything and set up smtp (similar to the google version like so )
this gives me (eg from here):

config.action_mailer.deconfig.action_mailer.delivery_method = :smtp
config.action_mailer.smtp_settings = {
  :address              => "smtp.live.com",
  :port                 => 587,
  :domain               => 'mydomain.com'
  :user_name            => 'username',
  :password             => 'mypass',
  :authentication       => 'plain',
  :enable_starttls_auto => true  }

ahh. I have finally solved this, I figure I'll post it to save somebody else the hassle. I had massive headaches trying to get this microsoft server to send from any address, my solution is now to use mandrill it's easy to configure and free for less than 12k emails per month.
(DISCLAIMER: I have no connection to Mandrill, please let me know any tips to allow the microsoft server to work, I couldn't and half a day was enough for me)

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Mike H-R
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1 Answers1

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I have basically identical settings as you but mine is working. I'm guessing your user_name is wrong, it should be 

:user_name => "username@mydomain.com"

and also make sure you've at least logged in once to your newly created account to activate it

mountriv99
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  • ah, thanks, I can't remember whether I tried that (that could have been the problem). Cheers for the help. – Mike H-R Nov 14 '13 at 11:48