The rise of the Internet of Things (IoT) has enabled the development of measurement systems dedicated to preventing health issues and monitoring conditions in smart homes and workplaces. IoT systems can support monitoring people doing computer-based work and avoid the insurgence of common musculoskeletal disorders related to the persistence of incorrect sitting postures during work hours. This work proposes a low-cost IoT measurement system for monitoring the sitting posture symmetry and generating a visual alert to warn the worker when an asymmetric position is detected. The system employs four force sensing resistors (FSR) embedded in a cushion and a microcontroller-based read-out circuit for monitoring the pressure exerted on the chair seat. Java-based software performs the real-time monitoring of the sensors’ measurements and implements an uncertainty-driven asymmetry detection algorithm. The shifts from a symmetric to an asymmetric posture and vice versa generate and close a pop-up warning message, respectively. In this way, the user is promptly notified when an asymmetric posture is detected and invited to adjust the sitting position. Every position shift is recorded in a web database for further analysis of the sitting behavior.