Private supplementary tutoring, widely known as shadow education, has become a global phenomenon. It has a range of providers, including commercial companies, university students desiring extra pocket money, and regular school teachers who provide tutoring as a sideline activity. This paper focuses on the last category. Governments are commonly ambivalent about the existence of shadow education, and may especially disapprove of regular teachers providing private supplementary tutoring in part because they fear that the teachers will neglect their main duties. With such matters in mind, some governments have attempted to prohibit teachers from providing private tutoring. However, such prohibitions are difficult to implement. This paper analyses situations in Korea, Mauritius, Kenya and England in order to derive comparative lessons from experience. It demonstrates the importance of wider contextual factors including alignment of macro-level aspirations with the micro-level perspectives of families finding themselves in increasingly competitive environments.