LLVM usually specifies executable names without extension so that they work portably across platforms. Occasionally, if you're writing something platform specific, you might want to specify the extension. For example, you might want to write a test that invokes a batch file. It's awkward to say `foo` when the file is really called `foo.bat`, but in this case `lit.util.which()` currently won't find it because it will construct the filename `foo.bat.bat`.
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