The regulation of organisational rights in South African law remains fraught. With reference to recent and contentious case law, this article considers selected questions which remain outstanding. In particular,the Constitutional Court’s decision in Police & Prisons Civil Rights Union v SA Correctional Services Workers Union & others is discussed, and aspects of the various judgments are critiqued. Whether organisational rights may be effectively categorised as statutory or contractual in nature is a highlighted issue. In addition, the definition of the workplace as it has been applied by both the Commission for Conciliation, Mediation and Arbitration and the courts is reviewed, along with the capacity of unions to acquire organisational rights through the statutory scheme, notwithstanding the nature of their membership. In conclusion, the author recommends that while clarity and certainty are urgently needed, they must be achieved in a way that facilitates the acquisition of organisational rights (in terms of the LRA) by trade unions, given the challenges which unions face today.