jacob
If the magenta cylinder is very rigid in comparison with the stiffness of the elastic bedding, then no gapping due to uplift occurs and thus there is no need for modelling "only-compression" contact. But if the optimum topology of the magenta cylinder be not very stiff in comparison with the elastic bedding, then there is a risk of local gapping between the magenta cylinder and the bedding.
Maybe as a first try, we can neglect the contact and find the optimum shape of the magenta cylinder, then we can see if there is any significant tension in the elastic bedding or not. If there is no tension applied to the elastic bedding or the gapping zone is limited in size, then we can consider that the topology found for the structure is sufficiently correct.