We survey some known results about operator semigroup generated by operator matrices with diagonal or coupled domain. These abstract results are applied to the characterization of well-/ill-posedness for a class of evolution equations with dynamic boundary conditions on domains or metric graphs. In particular, our ill-posedness results on the heat equation with general Wentzell-type boundary conditions complement those previously obtained by, among others, Bandle-von Below-Reichel and Vitillaro-Vazquez.