Working in IT, we see the behind-the-scenes of dozens of businesses. To many, a Point of Sale (POS) system is often viewed as just a digital cash register. It’s actually the central nervous system of a modern business. When it works, it is invisible; when it fails, the entire operation grinds to a halt. As we move through 2026, the complexity of these systems has reached an all-time high. Here are five of the biggest challenges we see businesses facing today from an IT perspective.