The present technology relates generally to cough-assist devices with humidified cough assistance. In one example, a system includes a cough-assist device having a first phase configured to provide insufflating gas to a patient circuit and a second phase configured to draw exsufflating gas from the patient circuit. A humidifier is disposed between the cough-assist device and a distal end of the patient circuit, the humidifier including a chamber configured to contain heated water and fluidically coupled to the cough-assist device and the patient circuit. The system further includes a bypass configured to (a) direct insufflating gas from the cough-assist device through a first route to the patient circuit such that the insufflating gas is humidified in the chamber, and (b) route exsufflating gas from the patient circuit through a second route to the cough-assist device such that the exsufflating gas bypasses the chamber.