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: Test Doesn't Fail
All I can think of is to look at the Console log to see if there are any messages there that might be relevant.
Re: Test Doesn't Fail
Nothing at all in the logs. I'm setting a lower timeout (no reason to wait two minutes, let alone the eight) and that causes a fail (which I want) when the server isn't available. I'll let you know if that isn't enough.