Updating SQL Server Management Studio (SSMS) and SQL Server is essential for bug fixes and minor improvements. It is advisable to schedule updates between projects to avoid disruptions, as unexpected issues can arise during an upgrade that may require significant troubleshooting. Upgrades should be approached cautiously, especially if they could affect project timelines or require extensive regression testing. While maintaining the latest release for your SQL Server version is recommended, updates to SSMS can be more flexible, allowing for easy reinstallation if problems occur. Overall, careful planning and timing are crucial for successful updates, ensuring that they do not derail project delivery.