Risk assessment is crucial to the increase of software development project success. Current risk assessment approaches provide only a rough guide. Risk assessment experts and domain experts are required in conducting risk assessments in software projects. Therefore, traditional risk assessment approaches require extra activities besides development tasks, and possibly leading to extra costs. We believe that an effective risk assessment approach should be transparently embedded in software development process. This paper aims to present an automated risk assessment framework using CMMI and risk taxnomy as a guidance to develop a risk assessment model. A pragmatic approach will be applied as a basis in building this suggested risk prediction model and the case studies of our practice. These studies are considered as our proof of concept.