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Even though integrating IT (Information Technology) and business leads to more profits and increased effectiveness, this is often accompanied by information security risks because many current businesses are carried out via the Internet. Re-engineering business processes and re-designing business models may improve the resistance of enterprises to information security threats and risks. In this case nevertheless, the software application (and portal) developers should take into account the pitfalls of the latest technologies. The usage of intelligent tools that are realizing system security auditing and are recommending (supported by especially constructed expert systems) corresponding actions, may be valuable for both business executives and software developers. Hence, a new paradigm is needed, reflecting the concepts of secure application development and communication between all participants and stakeholders involved in the application development process.