Machine learning has had a major impact on Finance and other organisations. The technology has developed at an astounding pace to undertake complex and technical tasks, and those that are both time consuming and that are subject to constantly changing parameters. The purpose of this article is to explore whether machine learning is a potential tool or solution that can help lighten the compliance and regulatory burden on charitable organisations in the United Kingdom; so that they are able to navigate regulatory compliance with legal duties and develop a coherent but streamlined action plan to shape future technological investment. The question is approached through data analysis, review of literature, and via a discussion of domestic and international regulation. Part one of the article summarises the current regulatory obligations that charities must meet, these are then, in part two, set against the potential technological solutions provided by machine learning as of August 2021. The recommendation is that charities can utilise machine learning as a smart technological solution, this will aid them to meet the regulatory challenges and comply with the law and/or rules. This work is original because it explores whether the various forms of machine learning can assist charities in meeting their regulatory compliance obligations.