A significant challenge in education today is the disconnect between educators and IT departments. Educators often feel frustrated when IT departments block or do not support new features, extensions, or apps that they find valuable for teaching. On the other hand, IT staff frequently express frustration over demands from educators that may pose security risks or require extensive time and resources to evaluate and implement. These two groups often misunderstand each other's perspectives and constraints, leading to a cycle of frustration and inefficiency. Educators need IT's support to innovate and integrate technology effectively, while IT departments need to ensure the security and stability of the school's digital infrastructure. When educators and IT professionals sit together and discuss their needs, positions, and constraints, they can achieve a deeper understanding and develop collaborative solutions that enhance educational outcomes without compromising security. The challenge is fostering this communication and collaboration consistently to bridge the gap between innovation and safety. This issue is critical because without mutual understanding and cooperation, schools risk either stifling technological innovation or compromising their digital security. Finding a balance is essential for creating a productive, innovative and safe educational environment.