I'm experiencing an issue where my macros with "At Login" trigger condition do not execute.
I've made sure the macros are enabled, their macro group is likewise enabled (and always activated), and the Engine is set to lunch at login, which it does.
I'm running KM 9.0.5 on Catalina 10.15.4.
I would appreciate if anyone has any ideas how I could troubleshoot this. Also if there is any other useful info I can provide please let me know.
I am not running Catalina, but it seems to have some issues.
Try splitting this macro into two separate ones
One triggered at login
One triggered at engine launch
and see which one or both work
The status menu is just to check they are working
Finally, they could both call a "common" macro for your initialisation stuff.
Thank you for the input.
I was about to start troubleshooting with your proposed test. However, I first restarted the computer and... the triggers suddenly started working. I repeated two more times and they continued to work.
I'm going to chalk it up to the long list of "Just Catalina Things". 
I will reopen if things break again.
When I started my PC this morning, I got a weird start up Alert... left me very puzzled until I realise it was from the example start/login trigger I used to answer this question, which was still active.