Detailed answer
Factors That Change The Recommendation
Leaks have seasonality. They show up at predictable times - and the predictable times are usually when contractors are busiest and emergency response is slowest. Knowing when your roof is most likely to fail lets you get ahead of it.
First heavy rain after a dry stretch is the universal trigger - dried sealants, brittle vent boots, and shifted flashing all fail when water finally arrives. In California, that's typically the first atmospheric river of November or December. In New Jersey, it can be late summer thunderstorms or fall nor'easters depending on the season pattern. Winter creates a second peak in northern markets: snow melts during the day, refreezes at the cold eave overnight, and that ice formation pushes water back under shingles. Major wind events (gusts over 50 mph) lift shingle tabs and break seals - leaks may not appear immediately but show up at the next rain. Pre-season inspection (October for California, September for New Jersey) catches issues before the peak failure window.
If You're In California Or New Jersey
California first-rain leaks peak in November-December as the atmospheric river season begins. New Jersey shows two peaks - late October through November for fall storms, and February for freeze-thaw and ice-dam damage.