PostgreSQL's upgrade process is often daunting due to its reputation for being laborious and potentially error-prone. However, the community recommends upgrading as soon as possible to take advantage of new features and security patches. The best approach depends on various factors such as the size of the change, performance gains, security fixes, and built-in function improvements. A general guideline is to upgrade major versions when they reach a minor version (e.g., 10.2, 11.2, 12.2), minor upgrades as available, and immediately if more than two major versions are behind. Timescale Cloud offers an automated approach to upgrading PostgreSQL versions, allowing users to safely test and deploy new versions with minimal downtime. By using the platform's features such as database forks and service upgrades, users can plan their upgrades ahead of time and minimize potential disruptions.