The present work addresses the problem of determining under what conditions the impending slip state or the steady sliding of a linear elastic orthotropic layer or half space with respect to a rigid flat obstacle is dynamically unstable. In other words, we search the conditions for the occurrence of smooth exponentially growing dynamic solutions with perturbed initial conditions arbitrarily close to the steady sliding state, taking the system away from the equilibrium state or the steady sliding state. Previously authors have shown that a linear elastic isotropic half space compressed against and sliding with respect to a rigid flat surface may get unstable by flutter when the coefficient of friction mu and Poisson's ratio nu are sufficiently large. In the isotropic case they have been able to derive closed form analytic expressions for the exponentially growing unstable solutions as well as for the borders of the stability regions in the space of parameters, because in the isotropic case there are only two dimensionless parameters (mu and nu). Already for the simplest version of orthotropy (an orthotropic transversally isotropic material) there are seven governing parameters (mu, five independent material constants and the orientation of the principal directions of orthotropy) and the expressions become very lengthy and literally impossible to manipulate manually. The orthotropic case addressed here is impossible to solve with simple closed form expressions, and therefore the use of computer algebra software is required, the main commands being indicated in the text.