I understand how powerful windbg can be at debugging, but when is an appropriate or best time to use it to debug an issue? Is it more issue specific, or just experience, intuition, and knowing that using it can just get the job done best?
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It’s a little bit of all those things, and a lot of personal perference. Many WinDbg people only use WinDbg so that’s what they are best at debugging with.
WinDbg also has some good extensions out there like SOS. So a particular extension might provide you with the specific piece of information that another debugger does not.
One reason to use a different debugger in certain circumstances is if you believe the debugger is incorrect. This is rare of course. For things like stack walking for instance, the debuggers use different methods, so you can confirm the stack is what you expect by using the other.
So sum up, for most issues it doesn’t matter. It’s whatever you are best at using. For some particular issues it’s what you say, knowing which tool is the best for that particular issue.