Practical problem-solving provides information technologies and information systems professionals with various learning and assessment opportunities to build, operate, and test cloud infrastructures. When carried out under simulated conditions, the challenge-oriented exercises offer a hands-on approach to highlight the importance of skills related to structured decision-making and detailed configuration in a command line. Therefore, this paper proposes a novel information system design solution for skill evaluation. It contains a data analysis component as an integral part, incorporates a secure sandbox, and analyses user-supplied command line data from cybersecurity training sessions. The proposed solution focuses on command-line input parsing, tokenization, and structured analysis, providing a viewpoint on the knowledge level in simulated scenarios. The paper aligns the needs of trainees and instructors with the learning process. The work provides insight into structured command-line data analysis and the complexities of command execution. The prototype is based on modular Bourne-Again Shell and Python modules and asynchronous data collection. The paper contributes to the educational processes by offering an information system solution to satisfy the assessment needs in the exemplified field of penetration testing of information systems.