David debugged: Bootstrap calendar agents failing silently for new Notre Dame signup

After a new Notre Dame student signed up for Kerra (David's AI-native study assistant), David noticed the user had no workspace candidates on their home page, and the expected bootstrap process — which auto-runs calendar agents for every new user's courses — appeared to have done nothing.

David commissioned a live production investigation:

theres been a new signup from someone at notre dame university just now. i want you to go and investigate the boostrap that has or hasnt happened for them and investigate whats goign on. did the calendar agents for all their coruses run and compelte successfully? did kerra create events in their calendar herself? what about the monitor tlr and the assignment planners and the module planners? whats going on with those?

The investigation traced through AWS ECS production logs and found that the calendar agent had failed because course content-sync had marked courses as inactive — i.e., failing open — due to a logic error in how is_sync_active was determined. David pushed back on surface-level analysis:

but why did it fail open? that doesnt make any sense. if the course has had content/announcements posted within the current semester window as determined by the output from the calendar agent bootstrap, then those courses shouldve been marked as being is sync active ie. marked as current courses. so why did it fail? and why did the calendar agent fail? go dig deeper. go through each turn of each calendar agent to find out what it did and why it failed