In the morning of 23 August 2017, around 3×106 m3 of granitoid rock broke off from the eastern face of Piz Cengalo, southeastern Switzerland. The initial rockslide–rockfall entrained 6×105m3 of a glacier and continued as a rock (or rock–ice) avalanche before evolving into a channelized debris flow that reached the village of Bondo at a distance of 6.5 km after a couple of minutes. Subsequent debris flow surges followed in the next hours and days. The event resulted in eight fatalities along its path and severely damaged Bondo. The most likely candidates for the water causing the transformation of the rock avalanche into a long-runout debris flow are the entrained glacier ice and water originating from the debris beneath the rock avalanche. In the present work we try to reconstruct conceptually and numerically the cascade from the initial rockslide–rockfall to the first debris flow surge and thereby consider two scenarios in terms of qualitative conceptual process models: (i) entrainment of most of the glacier ice by the frontal part of the initial rockslide–rockfall and/or injection of water from the basal sediments due to sudden rise in pore pressure, leading to a frontal debris flow, with the rear part largely remaining dry and depositing mid-valley, and (ii) most of the entrained glacier ice remaining beneath or behind the frontal rock avalanche and developing into an avalanching flow of ice and water, part of which overtops and partially entrains the rock avalanche deposit, resulting in a debris flow. Both scenarios can – with some limitations – be numerically reproduced with an enhanced version of the two-phase mass flow model (Pudasaini, 2012) implemented with the simulation software r.avaflow, based on plausible assumptions of the model parameters. However, these simulation results do not allow us to conclude on which of the two scenarios is the more likely one. Future work will be directed towards the application of a three-phase flow model (rock, ice, and fluid) including phase transitions in order to better represent the melting of glacier ice and a more appropriate consideration of deposition of debris flow material along the channel.