I'm experimenting with sending email from Simon via SMTP through our Office 365 domain, but it doesn't appear to work with Simon right now.
Microsoft's page on Client SMTP Submission says: "Confirm that your device or application supports Transport Layer Security (TLS) for SMTP on either port 587 or port 25 (587 is recommended)."
Simon's SMTP setup has a checkbox for SSL, but nothing that I can find regarding TLS. I did a bit of research and it seems like TLS is the successor to SSL for email submission and an up-and-coming protocol for security, so perhaps something that Simon should support.
Thanks!
Re: TLS security in Simon Email SMTP Notifier
SSL and TLS are basically the same thing; TLS is the name for newer versions of SSL.
I plan to add a new mail framework to the next version of Simon (working on it today, in fact), which may work better with your server.