Companies and government ministries alike have been rapidly shifting from the brick-and-mortar to the brick-and-click business model following the tremendous improvements in telecommunications infrastructure, coupled with the ever increasing competitiveness and global influences in local industries. Security unquestionably plays a pivotal role in any online presence. Websites that are built and maintained with a greater awareness of security issues have become more difficult targets for those with malicious intentions. These individuals have begun to shift their focus to softer targets both as the primary goal and as launching pads for other attacks. The aim of this paper is to highlight the susceptibility of businesses in Jamaica to these types of attacks by presenting the results of tests conducted on a representational subset of well established businesses operating in Jamaica with an online presence. We also discuss how the tests were conducted and the nature and consequences of the security flaws discovered.