In today’s digital environment, where society faces cyber threats, security is a key component of any organization. Penetration testing is crucial in detecting and eliminating security weaknesses before real attackers can use them. In reality, software penetration testing mimics real-world attacks on software applications to detect vulnerabilities, i.e., security vulnerabilities that real attackers could exploit. The testing requires careful planning, precise performance, and a thorough analysis of the results. This paper deals with successful penetration testing, starting with the basic steps of planning and defining the scope of the test itself. An overview of all tools and techniques and the importance of choosing the right tools for penetration testing are presented. The paper provides a comparative analysis of key tools for penetration testing, including practical guidelines for choosing appropriate methodologies and frameworks. Penetration testing requires a continuous approach as threats and vulnerabilities evolve with technology development. Through regular testing and updates of security policies, organizations can ensure the security of their own software systems.