Hi @mr_ensing. Have all the parts involved with these event triggers existed for a while, and those triggers worked just fine in those specific files before, but they suddenly stopped working, or are these 'new' parts that you are having troubles with? Were all the Event Triggers settings done manually, or were some created by code process? One odd situation we have encountered numerous times over the years when creating or editing the Event Triggers settings by code is that the settings appear to be created just fine, but the triggering is just not happening, until some manual interaction afterwards, similar to what you described to fix this issue. In those cases, the problem seemed to have stemmed from that specific document not having a 'DocumentInterest' assigned to it for the iLogic ApplicationAddIn. In my latest solutions for creating or editing the Event Triggers settings, one of the very first things I do is check for that, and if not found, I simply add a temporary, empty, internal iLogic rule to that document first, then proceed to create or edit those settings, then check for that specifically named, temporary rule, and if found, delete it. That simple act of adding an internal iLogic rule to the document, adds a DocumentInterest to the document for the iLogic ApplicationAddin. It seemed like when I just attempted to add a DocumentInterest for it directly by code, without any actual internal rules, or internal iLogic forms being present in the document, the new DocumentInterest would not stay there. That tip came from an Autodesk employee back around 2019, I believe. Not sure if that is the issue you are encountering though.
Wesley Crihfield

(Not an Autodesk Employee)