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What do the each of the watch window icons and overlays in Visual Studio represent? Is there a legend on an MSDN page somewhere?
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The Watch Window. The Watch Window allows you to see value of variables and expressions while debugging. It's kind of like the DataTip you get when hovering over a variable, except that you can write any expression you want. It's available from Debug | Windows | Watch | Watch 1 or Ctrl + Alt + W + 1.
Answer. The wrench icon signifies that you have enabled the System UI Tuner.
The icons identify the kind of the entity being watched; the same icons are also used in IntelliSense, Class View, and the Object Browser (and in Visual Studio 2012, the enhanced Solution Explorer).
There's an overview of the icons on MSDN: Class View and Object Browser Icons (the icons in Visual Studio 2012 are similar, but styled different).
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If you google for class and object browser icons then you should see the latest e.g. this one for VS 2019 https://docs.microsoft.com/en-us/visualstudio/ide/class-view-and-object-browser-icons?view=vs-2019
Some shown in this image from that page
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