A highly automated vehicle (HAV) is a safety-critical system. Therefore, a verification and validation (V&V) process that rigorously evaluates the safety of HAVs is necessary before their release to the market. In this paper, we propose an interaction-aware safety evaluation framework for the HAV and apply it to the roundabout entering, a highly interactive driving scenario with various traffic situations. Instead of assuming that the primary other vehicles (POVs) take predetermined maneuvers, we model the POVs as game-theoretic agents. To capture a wide variety of interactions between the POVs and the vehicle under test (VUT), we use level-k game theory and social value orientation to characterize the interactive behaviors and train a diverse library of POVs using reinforcement learning. The game-theoretic library, together with initial conditions, form a rich testing space for the two-POV roundabout scenario. On the other hand, we propose an adaptive test case generation scheme based on adaptive sampling and stochastic optimization to efficiently generate customized challenging cases for the VUT from the testing space. In simulations, the proposed testing space design captured a wide range of interactive situations at the roundabout scenario. The proposed test case generation scheme was found to cover the failure modes of the VUT more effectively compared to other test case generation approaches.