We study a model for the entanglement of a two-dimensional reflecting Brownian motion in a bounded region divided into two halves by a wall with three or more small windows. We map the Brownian motion into a Markov Chain on the fundamental groupoid of the region. We quantify entanglement of the path with the length of the appropriate element in this groupoid. Our main results are a law of large numbers and a central limit theorem for this quantity. The constants appearing in the limit theorems are expressed in terms of a coupled system of quadratic equations.