Online tracking is fast becoming synonymous with stalking and is associated with privacy concerns. Countries are in a hurry to introduce new privacy legislature while compliance is becoming increasingly difficult to adhere to. This is paving the way for many country- and region-specific rules to creep in instead of building more universally accepted rules and norms. With the ongoing development of connected technologies, more services are becoming available to business enterprises that have cross-domain tracking capabilities as the underlying technology. Importantly, the privacy responsibility is passed on to the business practitioners by tracking services, as those services are invisible to the users of those services. This research uses a simulated network environment to test, verify and describe information security and privacy vulnerabilities associated with some of the common technologies in use today. We describe how privacy can be compromised as individuals and businesses prefer convenience over data protection. This study will enable practitioners to assess risks, evaluate responsibilities and make informed decisions regarding usage of those technologies.