An enclosed cannabis cigarette preparation system that includes an indexing module configured to accept a plurality of pre-rolled cones, each having a sealed end and an open end, and to move the pre-rolled cones through a plurality of stations. The system further includes a filling module configured to dispense, at a first station, a portion of cannabis shake material into the open end of each of the pre-rolled cones to form loosely filled cones; a tamping module configured to compress, at a second station, the cannabis shake material in each of the loosely filled cones to form tamped cones; a de-clogging module; and a pinching module configured to pinch-twist, at a third station, the open end of each of the pre-rolled cones to form rolled cigarettes.