Coarse Mesh Finite Difference (CMFD) is a widely-used iterative acceleration method for neutron transport problems in which nonlinear terms are introduced in the derivation of the low-order CMFD diffusion equation. These terms, including the homogenized diffusion coefficient, the current coupling coefficients, and the multiplicative prolongation constant, are subject to numerical instability when a scalar flux estimate becomes sufficiently small or negative. In this paper, we use a suite of contrived problems to demonstrate the susceptibility of CMFD to failure for each of the vulnerable quantities of interest. Our results show that if a scalar flux estimate becomes negative in any portion of phase space, for any iterate, numerical instability can occur. Specifically, the number of outer iterations required for convergence of the CMFD-accelerated transport problem can increase dramatically, or worse, the iteration scheme can diverge. An alternative Linear Diffusion Acceleration (LDA) scheme addresses these issues by explicitly avoiding local nonlinearities. Our numerical results show that the rapid convergence of LDA is unaffected by the very small or negative scalar flux estimates that can adversely affect the performance of CMFD. Therefore, our results demonstrate that LDA is a robust alternative to CMFD for certain sensitive problems in which CMFD can exhibit reduced effectiveness or failure.