Current status of this is that I'm undertaking some preliminary refactoring of LLVM's testing infrastructure to make this kind of integrated test possible.

LLVM already has a set of debug info tests that are similar but test against other debuggers, so I'm going to repurpose that for the WinDbg tests.  The high-level refactoring stuff is almost done, at which point I can begin on the work necessary to script WinDbg.

While it's obviously very important, I'm not sure it actually blocks 709690.

Zach: any progress since your last update a month ago?

Depends what you mean by “progress”. I’ve submitted several large patches
to begin working towards this, but much of it was refactoring related and
there’s still at least one more refactoring patch that needs to happen
before i can even begin designing the test format, which itself needs to
happen before i can begin writing the thing that runs programs under cdb
with the tests.

Also agree that this should not really be a blocker for anything though

Just saw that rnk has a patch in progress here: https://reviews.llvm.org/D54187