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The most painful thing in Spy++ is the very thing that should be simple; Choosing a window to spy on. Each and every time I went through the same loop of mindless "click, drag, OK, right-click, select" I swore I was going to write a better way...but never did.
Then, during one particularly nasty debugging session I finally had enough of it. I was just so annoyed with clumsy way Spy++ operated that I dropped everything I was working on and started Winspector.
The first things I worked on was to improve the window selection, make the window list auto-refresh, and add the ability to watch window messages without having to select them. It was bliss.
I wrote Winspector not because I wanted to write such a tool but because I was left with little choice. I now look at people using Spy++ and I honestly can't believe they do it.
So, do yourself a favour stop working with a substandard tool and try Winspector.