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Simon 5 is coming soon!

Simon version 5 is currently in beta testing. It is a massive update, introducing a much-requested feature: syncing the Simon data between multiple Macs, plus a Simon Status service, a Link Checker filter, improved Find filter, iMessage and Speak Error notifiers, a new app icon, and much more.

Important: please note that Simon 5 requires a minimum of macOS 10.12 (Sierra), and will be a paid upgrade from Simon 4 after the beta. Purchasers since September 1, 2020 automatically get a version 5 license (that also works in previous versions).

Read the blog for details.

TLS security in Simon Email SMTP Notifier

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!

David Sinclair's picture

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.