The emails are sent manually.
Problem is that in a lot of cases competitions are organized pretty much a couple of days before they actually launch. We always ask for a 3-week up front notification, but in general the final "green-light" for a competition is given a couple of days before the start (with the PR available less than 24h before the start).
We try to inform people as fast as possible, actually.
Do you still have these issues? V1.2.1 should be a lot faster in general, and also the cookie issue has been resolved.
Hm, HWBOT Prime works okay here?
I tried the following path:
HWBOT -> Link to Challenger Div I -> Click Road To Pro -> Click on Division III shield -> brings me to Challenger Div III roadmap.
No 404.
That being said, or written, we did fix a small bug for the challenger divisions yesterday, so maybe that was the issue.