Provided is a method for defining and organizing computer breakpoints for use during a debugging operation of a software application. The claimed subject matter provides flexible breakpoints that are called depending upon the condition of the corresponding call-stack or, in other words, depending upon a specific calling sequence through which the module containing the breakpoint was reached. A novel type of breakpoint is provided that, rather than causing a halt in execution of a module, changes the state of one or more other breakpoints. In an alternative embodiment, a breakpoint is provided that determines whether or not to execute based upon an examination of the call-stack.