I read the leaked Halloween Documents—here’s what Microsoft feared most about Linux
I read the leaked Halloween Documents—here’s what Microsoft feared most about Linux
Publish Date: 2026-07-03 12:46:00
Source Domain: www.howtogeek.com
It’s a tale of terror, paranoia, and skeletons in the closet. Back in the late 1990s, Microsoft was riding high, with the recent success of Windows 95 cementing its hold on the home and office desktop market. So high, in fact, that the US government was about to indict it for holding a monopoly over the industry.
Microsoft had long engaged in dubious practices to gain and retain a commanding lead in the market for operating systems and office applications. But a plucky upstart named Linux was stalking the digital halls, and Bill Gates’ company had started looking over its shoulder, nervously, in fear of its very survival. Then, somebody let the cat out of the bag…
A series of haunting documents
A leaked memo saw Microsoft’s dirty laundry aired in public
The first Halloween document, titled “Open Source Software: A (New?) Development Methodology,” was authored by Vinod Valloppillil in August 1998, strictly for the eyes of Microsoft employees only. Valloppillil got the shock of his life two months later when the memo was leaked to Eric Raymond, an open-source software advocate. It’s safe to assume that was the one thing Vinod didn’t want to happen.
Raymond wasted little time in publishing the document, with copious annotations and commentary, explaining its context and adding his own takes. Since he received and published the memo around October 31, it later became known as one…
