A kernel-aware debugging system, medium, and method. The kernel-aware debugging system may include a kernel-aware debugging interface including a conditional breakpoint setting unit which sets a kernel-aware conditional breakpoint by checking a currently operating object inside a kernel of a target system when a central processing unit (CPU) of the target system stops operating at a particular position where the breakpoint is set and making the CPU proceed to operate when it is determined that it is not intended that the currently operating object be debugged. Moreover, the kernel-aware debugging interface may include a unit which stores control flow information for detecting faults due to asynchronous events, a profiling unit which collects profile information and allows back-tracing when faults occur, and a unit which debugs a synchronization problem between multitasks.