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Encryption has protected the Internet for some time now and it has come to raise user trust on the otherwise unsecure Internet. However, recent years have seen the use of robust encryption as stepping stone for cyber-criminal activities. Ransomware has not escaped the headlines even as it has attacked almost every sector of the society using a myriad of infection vectors. Mission critical data has been held to ransom and victims have had to part away with millions of dollars. The advent of the anonymous Bitcoin network has made matters worse where it’s been virtually infeasible to trace the perpetrators. In this paper, we endeavor to perform dynamic analysis of WannaCry ransomware samples based on malwarefree infection vectors. Further, we perform reverse-engineering to dissect the ransomware code for further analysis. Results show that despite the use of resilient encryption, the ransomware like other families in the wild uses the same attack structure and cryptographic primitives. Our analysis leads us to the conclusion that this ransomware strain isn't as complex as previously reported. This detailed practical analysis tries to raise awareness to the business community on the realities and importance of IT security whilst hinting on prevention, recovery and the limitations thereof.