One file for each day you rode — from a Garmin, from Strava, or as a GPX from anything else.
A film is built from the days you rode, and How It Went needs one activity
file for each of them. It reads three things: the zip Garmin Connect hands
you, a bare .fit, and .gpx from anything that
writes one. Whichever you have, the app's Rides step takes
them all at once and lays them out as days.
Garmin Connect's website will hand you the file your device actually wrote — a zip with the ride inside, carrying the totals your head unit showed you, where you stopped, and everything the bike sent. It is worth the detour over a GPX of the same ride, and it is five steps.
The app connects to Strava and lists your rides, which is the shortest route there is — no files, no browser, and it only happens once. Access is limited while How It Went is new, so the app can tell you it cannot connect; a file works in that case and the guide says which.
Komoot, Ride with GPS, Wahoo, Apple Fitness, Suunto, COROS and the rest all export a GPX. Export the ride, then send it to How It Went through the share sheet, or tap Choose files and pick it. A GPX carries the track and a handful of channels rather than the whole recording, which is fine — it is what most of these services can give you.
Open the trip's Rides step. It says Start with your rides, with Choose files under it; on a Mac you can drag the files onto the window instead. Take every day at once rather than one at a time — the days come out of the timestamps, so a week of rides arrives as a week. A trip can mix all three kinds in one go.