The engineering world appears today more mature than ever in providing stable technology premises in order to build large scale, real interoperable and secure enterprise information systems, and strengthening the fundamental structure of private and public organisations. However, as technology has evolved, more opportunities have become available for virus writers to express their imagination in malicious code. Computer viruses are a major problem in modern day computing, threatening the structure of organisations, their enterprise systems and eliminating user-acceptance of electronic and mobile services provided. Detection tools such as virus scanners have performed poorly, particularly when facing previously unknown virus or novel variants of existing ones. This paper proposes and performs assessment on advanced proactive and reactive cryptographic measures that ensure the robustness and security of enterprises and computer systems.