Hello Jake! The system updates are not tracked by triggers so when the scheduled task sets the 'FourDays' field to 'Yes', the trigger won't run. It would be easier for you to send the notifications right in the scheduled task but it turned out that the action does not support tokens in the scheduler. I will consult with developers whether we can support them there.
As regards the error you encountered, I could not reproduce it and your configuration seems alright. Please ensure that you use the latest HelpDesk version (Settings > About) and clear browser cache. If the issue persists, load the page in incognito mode, open developer tools (F12), switch to the ‘Network’ tab, press Ctr+R, and reproduce the issue. Then export a HAR file:
Switch to the ‘Console’ tab, open the context menu of any record and save the logs:
Send the collected data and the screenshot of the error to support@plumsail.com and refer to this topic.