What if the SSL handshake fails intermittently? What could be causing that?

Intermittent failures suggest a less consistent issue. Possible causes include: temporary network connectivity problems between Cloudflare and Heroku, rate limiting on certificate validation, or issues with Heroku's dyno scaling (if a dyno restarts during the handshake). Monitoring Heroku's performance metrics and Cloudflare's analytics can help identify patterns and pinpoint the root cause. Also, check for any recent changes to your Heroku app or Cloudflare configuration.