This achievement is supposed to be awarded for catching 50 shoplifters. However, its description is inaccurate and if taken quite literally one could spend many hours and never get it. You can't grind it by rewinding days, it is achieved in single playthrough and the rewind function can be used to get a better result if you missed an opportunity to arrest someone. Remember to start over or rewind immediately. If you rewind more than just to previous day, you'll loose all your progress after that day.