White & Black box Debuggers, Intelligent Debugging, and Dynamic Analysis

Debugging is a common task for data scientists, programmers, and security experts alike. In good ole RStudio we have a nice, simple built-in white-box debugger. For many analysis-oriented coders, the basic debugging functionality of an IDE like RStudio is all they know and it may be a surprise that debugging is a bigger, much sexier, topic. Below I define and describe key topics in debugging and dynamic analysis, as well as provide links to the most cutting edge free debuggers I use.

Dynamic Analysis: Runtime tracing of a process, usually performed using a debugger. Dynamic Analysis is critical for exploit development, fuzzer assistance, and malware inspection.

Debugger: a program that is used to test and troubleshoot other programs.Intelligent Debugger: a scriptable debugger that supports extended features such as call hooking, such as Immunity Debugger and PyDbg.

White Box Debugger: Debuggers built into IDEs and other dev platforms, which enable developers to trace through source code with a high degree of control, as to aide in the troubleshooting of functions and other code breakages.
Black Box Debugger: Used by bug hunters and reverse engineers, black box debuggers operate on compiled programs when the source code is not available and the only information is available in a disassembled format. There are two broad subclasses of black box debuggers, which are user mode (i.e. ring 3) and kernel mode (i.e. ring 0).
User mode black box debugger: a processor mode under which your applications run, usually with the least amount of privilege (e.g. double clicking PuTTY.exe launches a user-mode process).
Kernel mode black box debugger: a processor mode where the core of the OS runs using the highest amount of privilege (e.g. capturing packets with a network adapter that is in passive mode).
User-mode Debuggers Commonly used among Reverse Engineers
WinDbg by Microsoft
OllyDbg by Oleh Yuschuk, a F.O.S.S. debugger
GNU Debugger (gdb), a F.O.S.S. Linux debugger by the community