As current trends in software development move toward more complex object-oriented programming, inlining has become a vital optimization that provides substantial performance improvements to C++ and Java programs. Yet, the aggressiveness of the inlining algorithm must be carefully monitored to effectively balance performance and code size. The state-of-the-art is to use profile information (associated with call edges) to guide inlining decisions. In the presence of virtual method calls, profile information for one call edge may not be sufficient for making effectual inlining decisions. Therefore, we explore the use of profiling data with additional levels of context sensitivity. In addition to exploring fixed levels of context sensitivity, we explore several adaptive schemes that attempt to find the ideal degree of context sensitivity for each call site. Our techniques are evaluated on the basis of runtime performance, code size and dynamic compilation time. On average, we found that with minimal impact on performance (+/-1%) context sensitivity can enable 10% reductions in compiled code space and compile time. Performance on individual programs varied from -4.2% to 5.3% while reductions in compile time and code space of up to 33.0% and 56.7% respectively were obtained.