Decisions regarding information system evolution strategy, including modernization or replacement, are economically significant. Selection of a proper method for analyzing potential options, acquisition of suitable metrics or follow-up data, and evaluation of the results are major challenges in the evolution strategy decision making. In order to address these challenges, a framework for Information System Evolution Benefit Assessment (ISEBA) was developed. ISEBA provides assistance in the selection of a benefit-evaluation method for the investment situation at hand. It is based on empirical research on industrial decision making and co-operation projects, and examination of existing research results from information technology investment-evaluations. Based on the experiences from real world industrial cases, it can be alleged that ISEBA suits its purpose. It makes a decision maker take note of relevant issues in evolution investment decision making, leads to the selection of suitable appraisal method, and promotes discussion of the value of the results. Among the results of the industrial cases, the following was found. Firstly, resources are an important factor influencing the selection of an investment assessment method. Secondly, the appearance of both tangible and intangible benefits is scattered with respect to time and organizational structure. Thirdly, a dichotomy exists between upper management decisions and lower level organizational goals. The benefit appraisal was focused on an operative level while real project objectives were set on a strategic level. It is concluded, that a need for a practical framework, such as ISEBA, exists.