Method and apparatus for enhancing an executable is disclosed herein. In one embodiment, the method includes instrumenting an executable with additional program code to detect run-time errors, and while running the instrumented executable within a debug environment generating the run-time errors detected by the additional program code, upon reaching a breakpoint, identifying any of the run-time errors which occurred while executing a function in which the breakpoint is located, and transmitting an indication of the identified run-time errors to the debugging environment.