Joshi, A.PBandrevu,SKaur, NSharma,IMaduranga, M.W.P.Wanniarachchi, W A A M2026-05-142025-09-092961-5011https://rda.sliit.lk/handle/123456789/4984As the yber threat increases, it becomes necessary for organizations to start securing their digital valuables and infrastructures. This research is mainly about analysing the weaknesses lying in the vulnerabilities of the HTTP and SSH protocols. Investigation here is into how the intruder can escalate his privileges and illegally access computers. Under open-source tools like Netcat and Gobuster, the article examines the vulnerability-assessment methodologies culminating in root access to the target machine. This paper emphasizes the need for proactive security measures and gives recommendations on improving defences against future attacks. The study, as bright as the findings may be, awaits empirical dimensions to affirm the proposed measures.enCybersecurityHTTP vulnerabilitiesSSH vulnerabilitiesprivilege escalationreverse shellpenetration testingPenetratingz the Defenses: An Investigation into the Achilles Heel of HTTP and SSHConference Paperhttps://doi.org/10.54389/MGQF6691