IT has become a production means for many organizations and an important element of business strategy. Even though its effective management is a must, reality shows that this area still remains in its infancy. IT management relies profoundly on relevant information which enables risk mitigation or cost control. However, the needed information is either missing or its gathering boils down to daunting tasks. We propose an approach to recovery of management information from the essence of IT; the software’s source code. In this paper we show how to employ source code analysis techniques and recover management information. In our approach we exploit the potential of the concealed data which resides in the source code statements, source comments, and also compiler listings. We show how to depart from the raw sources, extract data, organize it, and eventually utilize so that the bit level data provides IT executives with support at the portfolio level. Our approach is pragmatic as we rely on real management questions, best practices in software engineering, and also IT market specifics. We enable, for instance, an assessment of the IT-portfolio market value, support for carrying out what-if scenarios, or identification and evaluation of the hidden risks for IT-portfolio maintainability. The study is based on a real-life IT-portfolio which supports business functions of an organization operating in the financial sector. The IT-portfolio comprises Cobol applications run on a mainframe with the total number of lines of code amounting to over 18 million. The approach we propose is suited for facilitation within a large organization. It provides for a fact-based support for strategic decision making at the portfolio level.