Windows 2.0

Windows 2.0 shipped December 9, 1987, and did the one thing its predecessor had been forbidden from doing: it let windows overlap. Microsoft’s lawyers had kept Windows 1.0 tiled specifically to avoid echoing the Macintosh, but by 1987 the company judged the interface war worth the risk, and Windows 2.0 arrived with stackable, resizable windows, title bars, and a taskbar-adjacent look that read as unmistakably Mac-like. It also brought 16-color VGA graphics and, in its Windows/386 variant, a protected-mode kernel that could run several MS-DOS programs at once with real preemptive multitasking — the first time a Microsoft GUI product did more than sit decoratively on top of DOS. Apple noticed immediately. In March 1988 it sued Microsoft and Hewlett-Packard, itemizing 189 separate interface elements — overlapping windows chief among them — as copyrighted expressions of the Lisa and Macintosh lifted wholesale.

The lawsuit outlived the software by years. A federal court ruled in 1992 that 179 of Apple’s 189 elements had already been licensed to Microsoft under the 1985 Windows 1.0 agreement, and that the rest were either unoriginal or the only practical way to express the underlying idea; the Ninth Circuit affirmed in 1994, and the Supreme Court declined to hear Apple’s appeal in 1995. By then Windows 2.0 itself had been gone from active development for years, replaced by Windows 2.1 in May 1988 and then eclipsed entirely by Windows 3.0’s 1990 commercial breakout. Microsoft kept the 2.0 code on its support rosters anyway, alongside 1.0 and 3.1, until it retired all three simultaneously on December 31, 2001. The specific overlapping-windows implementation that Apple had fought in court never itself resurfaced after 2.1 replaced it — the feature persisted, licensed and litigated clean, but the 1987 build that introduced it did not.