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).
Re: Email Notification failures
The Email notifier can be tricky to get configured. All I can suggest is trying various options; try without SSL, etc. Check the transport settings, and the From and To addresses. Failing that, you could use the Apple Mail transport.
Re: Email Notification failures
I am a new Simon user but pretty experienced in email and am frustrated that I cannot get the email notifications to send. The transport method is SMTP, server port 587, using SSL, authentication is Password. I am reluctant to have Apple Mail running on the machine, Simon should all run quietly in the background.
Re: Email Notification failures
Try the steps in my previous comment, if you haven't already. It does work, but can be difficult to get right. I am considering replacing the Pantomime framework with something else that is less picky, though there aren't many good options.