Cygwin het in [] begin as 'n projek van [[Steve Chamberlain]], 'n ingenieur by [[Cygnus Solutions|Cygnus]] wat opgemerk het dat Windows NT en 95 [[COFF]] gebruik as hulle [[objeklêerformaat]] en dat GNU reeds ondersteuning vir [[x86]] en [[COFF]] asook die C funksieversameling, [[newlib]], gebied het; wat dit dus teoreties nie baie moeilik sou maak om die [[GCC]] te verander om 'n samesteller te skep wat uitvoerbare programme vir Windows kon skep nie. Die vermoede is toe in die praktyk bevestig en is 'n prototipe vinnig ontwikkel.
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The next step was to attempt to bootstrap the compiler on a Windows system, but this required enough emulation of Unix to let the [[Autoconf|GNU configure]] [[shell script]] run, which requires a shell like [[bash]], which in turn requires [[Fork (computing)|fork]] and [[Standard streams|standard I/O]]. Windows includes similar functionality, so the Cygwin library proper just needs to translate calls and manage private versions of data, such as [[file descriptor]]s.
By [], other engineers had joined in, since it was clear that Cygwin would be a useful way to provide Cygnus' embedded tools hosted on Windows systems (the previous strategy had been to use [[DJGPP]]). It was especially attractive because it was possible to do a three-way cross-compile, for instance to use a hefty [[Sun workstation]] to build, say, a Windows-x-[[MIPS]] cross-compiler, which was faster than using the PC of the time. Starting around [], Cygnus also began offering the Cygwin package as a product of interest in its own right. ▲
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