A lively drug policy debate is going on in the UK, and a central theme emerging is the punishment of drug offenders. The main contributing voices draw attention to the largely futile position of prosecuting offenders through the criminal justice system who are drug addicted and/or who are caught in possession of small quantities of drugs for personal use. This paper adds to this discussion by reporting findings from observations carried out in London Magistrates’ Courts. It notes the relatively high prevalence of small quantity drug possession cases that appeared before the courts over the study days, and questions the value of this type of crime arriving here in the first place. It examines the resultant financial penalties that are most commonly dispensed, and asks whether they can be reasonably justified. It states these are harsh and depriving given the already economically disadvantaged status of most defendants. In addition, case details revealed issues of policing approach involving ‘stop and search’ and the variable application of police discretion. The paper calls for thought to be given to the damage caused to peoples’ lives through pursuing criminalising drug policies, and to the time and economic cost to stretched policing and criminal justice resources. It suggests we learn lessons from other European jurisdictions who assign drug possession for personal use cases, to an arm of the prosecution service where they are processed as ‘out-of-court’, ‘administration offences’.