Appointment Status Updates: We encountered issues where appointment statuses were not updating correctly once the scheduled time passed. This was due to edge cases in our APScheduler configuration. We resolved it by refining our scheduling logic and adding comprehensive error handling, ensuring that uncompleted appointments are marked as expired accurately.

SMS Notification Reliability: Integrating the Twilio API for SMS notifications initially resulted in intermittent message failures. By implementing retry mechanisms and enhancing our error logging, we improved reliability and ensured that critical appointment notifications were consistently delivered.

User Authentication Complexity: Managing secure authentication for both patients and doctors across modular Flask blueprints posed challenges. We streamlined this process by switching to Role based authentication system using the ClerkId as the User ID even in our backend but utilising a common database and optimizing our database models, resulting in a more secure and efficient login system.