Estimation is one of the most critical areas in software project management life cycle, which is still evolving and less matured as compared to many other industries like construction, manufacturing etc. Originally the word estimation, in the context of software projects use to refer to cost and duration estimates only with software-size almost always assumed to be a fixed input. Continued legacy of bad estimates has compelled researchers, practitioners and business organizations to draw their attention towards another dimension of the problem and seriously validate an additional component, viz. size estimation. Recent studies have shown that size is the principal determinant of cost, and therefore an accurate size estimate is crucial to good cost estimation. Improving the accuracy of size estimates is, therefore, instrumental in improving the accuracy of cost and schedule estimates. Moreover, software size and cost estimates have the highest utility at the time of project inception, when most important decisions (e.g. budget allocation, personnel allocation, etc). are taken. The dilemma, however, is that only high-level requirements for a project are available at this stage. Leveraging this high-level information to produce an accurate estimate of software size is an extremely challenging and high risk task. This study acknowledges the presence and effect of risk in any software estimate and offers pragmatic strategies for risk mitigation.