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Outlook works for me BUT you have to log into outlook.com webmail in the web browser on the same computer that you will be sending from otherwise spam protection prevents you from using the SMTP server.
Even if you do what I said above you will be spam blocked for various reasons, e.g. you haven't signed in to webmail for a long time or you send too many emails in a period of time
This is the settings I use
SMTP server: smtp.live.com
Connection Encryption: TLS
Authentication is plain password.
Also note that a DDR report run on the FileMaker file will reveal the email password.
The best way to do this is to use your own exchange server with the permissions opened up, then you can change the E-mail Address and Reply-To Address in FileMaker and send/receive email as whoever you want. Otherwise it is not so reliable.