A system for engineering and detailing joints in a steel structure includes a compute device that is electronically linked with a web-enabled server. In use, the system engages in an automated process of connecting the various joints in the steel structure by first collecting basic connection preferences via the compute device. Additionally, raw data is extracted from a computer model of the steel structure on the compute device. Using the connection preferences and raw data, the server analyzes framing interrelationships and engineers the connection details for each joint based upon connection preferences and load requirements. Taking into account the connection details of other local joints in the steel structure, the server utilizes an iterative engineering process to ensure that the connection details satisfy structural loads in a cost-effective fashion. Upon completion, the engineered connection details are uploaded back into the computer model of the steel structure on the compute device.