A method for debugging an executable is disclosed herein. The method begins by receiving one or more breakpoints related to a call stack in the executable. The processor receives an executable in a debug environment. The processor executes an executable until one or more breakpoints are hit. Upon detecting a breakpoint, the processor temporarily halts executing by transferring control to an analysis tool to gather information related to execution of the executable up to the breakpoint. The analysis tool gathers one or more predefined outliers. The processor receives control back from the analysis tool to continue execution in response to the analysis tool collecting relevant information in the executable.