This article aims to investigate the ability of Share Point and File Share Search Engines to ensure compliance with GDPR regulations. The value of this research is to contribute to academic theory and business literature on the capability of search engines to find personal data in internal and external data repositories and systems for GDPR compliance. Long term project outcomes are expected to lead to empirical results which added value to existing theory and be a foundation (or framework) for future research. Quantitative methods are used through a questionnaire and experiments to obtain data from a convenience sample from an IT and non-IT population of executives, administrators, and professionals who have exposure to Share Point and File Share data repositories. Evidence from the experiments demonstrated that under three conditions, the hypothesis can be rejected. This research, considering its limitations, has proven that personal data, metadata, and files cannot be found in all cases in Windows File Share and Share point repositories. In conclusion, improvements in search engines or enhancements of operational manipulations with data and metadata in files must be performed based on the conditions stated in the research conclusions to ensure accurate compliance with GDPR.