The ICSTRA 2021: 14. International Conference on Security Testing and Risk Assessment will be held on July 23 & 24, 2021 in London. This conference provides an opportunity for IT professionals, educators, academic scientists, and researchers to collaborate and share knowledge on security testing and risk assessments. Prospective authors who are working on this domain of testing can also submit their original papers on constructive, empirical, conceptual, experimental, and theoretical findings. All papers will be evaluated by three reviewers and high-impact papers have a chance to be published in the Special Journal Issue on Security Testing and Risk Assessment.