In this paper we analyze the convergence behavior of a sampling based system approximation process, where the time variable is in the argument of the signal and not in the argument of the bandlimited impulse response. We consider the Paley-Wiener space $PW_\pi^2$ of bandlimited signals with finite energy and stable linear time-invariant (LTI) systems, and show that there are signals and systems such that the approximation process diverges in the $L^2$-norm, i.e., the norm of the signal space. We prove that the sets of signals and systems creating divergence are jointly spaceable, i.e., there exists an infinite dimensional closed subspace of $PW_\pi^2$ and an infinite dimensional closed subspace of the space of all stable LTI systems, such that the approximation process diverges for any non-zero pair of signal and system from these subspaces.