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A canonical assumption in dynamic atomic force microscopy is that the probe tip interacts with the sample once per oscillation cycle. We show this key ansatz breaks down for soft cantilevers in liquid environments. Such probes exhibit “drum roll” like dynamics with sequential bifurcations between oscillations with single, double, and triple impacts that can be clearly identified in the phase of the response. This important result is traced to a momentary excitation of the second flexural mode induced by tip-sample forces and low quality factors. Experiments performed on supported biological membranes in buffer solutions are used to demonstrate the findings.