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: Incoming Mail (IMAP) - "Plaintext authentication ...
See the "Incoming Mail (POP) via SSL" service on the Simon Extras page. That is for POP, but could probably be modified for IMAP.
Re: Incoming Mail (IMAP) - "Plaintext authentication ...
Gave that a shot and it didn't work either. Used port 143. I also tried typing the command into terminal and seeing the results. Was getting an error. I don't have ssl enabled on our mail server. It's just MD5 encryption.
Re: Incoming Mail (IMAP) - "Plaintext authentication ...
If you can find a way to check it via Terminal, you could use that in Simon. Maybe a simple
telnet
session would work, though maybe not if there's encryption.