Pleural drain insertion is a commonly employed technique used for several indications, including the drainage of haemothorax and pneumothorax. Difficulties can be encountered without proper techniques, especially in obese patients. We describe and illustrate our stepwise approach used during chest drain insertion. The points emphasised include: appropriate use of sedation, use of local anaesthetics, pleural anaesthesia, making a deep incision in the intercostal space, using a proper size and type of haemostat to enter the pleura and dilate the tract, blunt dissection with a finger, using the haemostat to ensure basal or apical placement of the drain, fixation of the drain with a vertical mattress suture to secure the tube, and placing the drain on suction for effective evacuation of the pleural cavity. Insertion of a “surgical” drain requires special techniques and precautions to ensure safe and effective drainage of the pleural cavity. Ultrasound may also be utilised to aid drain placement. Understanding the “bubble and swing” after insertion is also explained in simple terms to guide aftercare of the drain and indications for removal. A description of a “clamp test” to guide the decision for removal, if required, is included. The evidence for optimal timing of removal in the respiratory cycle is also reviewed and explained in a stepwise approach with practical tips for patient counselling.