Overview: As one of the devs that worked on it at

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The Mind Behind Windows: Dave Cutler
The Minds Behind Windows: Raymond Chen
Windows Longhorn Explained by Dave Plummer - Retired Microsoft Engineer
The Real Reason Windows is Free - And what that costs you!
Why Multitasking on Windows Was So Hard (and How It Finally Worked)
Windows Longhorn and the Worst Code I've Ever Seen: Dave Cutler
Blame Me: I Worked on the Windows Progress Dialog!
Dave Plummer: Programming, Autism, and Old-School Microsoft Stories | Lex Fridman Podcast #479
Why I Deleted printf() from Windows COM in 1994!
01.Secret History of Windows Task Manager - Part 1 - Origins
Windows, Part I - Dave Probert
Microsoft's "Pathetic" Operating Systems - Steve Ballmer and Breakfast at Denny's with Dave Cutler

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