This paper presents our research efforts to synthesize complex instrumental gestures using a score-based control scheme. Our specific goal is to simulate the rasgueado technique that is popular especially in flamenco music. This technique is also used in the classical guitar repertoire. Rasgueado is especially challenging as ordinary music notation is not adequate to represent the dense stream of notes required for a convincing simulation. We will take two approaches to realize our task. First, we use the practical knowledge of how the actual performance is accomplished by the human player. A second, complementary, approach is to analyze an excerpt from real guitar playing. Our main focus here is to extract the onset times and the amplitudes of the recoded gesture. Next we combine the results from the two analysis steps using a constraintbased approach to find possible pitch and fingering sequences. Finally we translate the findings to our macro-note scheme that allows us to fill algorithmically a musical score.