As far as I know, you have absolutely no guarantee that a request goes to the same dyno as the previous request.
The best way to do this would probably be to either host the file somewhere else, like S3, or to send it immediately in the same request.
If you're generating the file in a background worker, then it most definitely won't work. Every process runs on a separate dyno.
See How Heroku Works for more information on their backend.