Technologies for generating a patient-specific surgical plan from medical image data include receiving an orthopaedic surgical plan request from a computing device of a healthcare facility via a network, receiving a medical image of bony anatomy of a patient, and receiving constraint data corresponding to an orthopaedic surgical procedure to be performed upon the bony anatomy of the patient. Such technologies may further include determining whether the orthopaedic surgical procedure to be performed upon the bony anatomy of the patient is a difficult orthopaedic surgical procedure, generating a first surgical plan for the orthopaedic surgical procedure to be performed in response to determining that the orthopaedic procedure to be performed is not a difficult orthopaedic surgical procedure, and generating a second surgical plan for the orthopaedic surgical procedure to be performed in response to determining that the orthopaedic procedure to be performed is a difficult orthopaedic surgical procedure.