A challenge that affects our community is the division between district IT departments and teachers in the classroom. IT values safety and security. Educators value teaching and learning. All these values are essential to education, but these groups struggle against each other to achieve their goals. This challenge matters because it has negative impacts on staff and students. Beginner teachers will attempt to take risks and try new technologies, only be blocked from online resources, get frustrated, and give up on innovation. This affects student engagement. When advanced teachers come up against obstacles online, they can hack the system to meet their needs, but it’s unsafe. This undermines student security. Inundated IT Directors see these security breaches and shut down access to preserve safety. They are doing what they think is best, but it interrupts student equity.