In 2004, European Union (EU) regulators ordered Microsoft to produce a “workable” programming manual that would allow companies that use other operating systems (like Linux) to utilize the “grammar rules” needed to build software programs that could communicate with Microsoft products. Microsoft complied with the request, which was part of the an EU anti-trust lawsuit against the softare giant, but not to the satisfaction of regulators. The EU asked Microsoft to rewrite the manual because they were “dismayed with its length and its disorganization” The Wall Street Journal reported(registration required).

Improvements to the manual were requested by the EU after an evaluation conducted by engineers from Oracle, Sun, IBM, and Novell. The evaluation process was tightly controlled by Microsoft, who allowed evaluators to bring “only pens or pencils with them into a secure room in Redmond, where the 12,000 page manual could be viewed only on a computer screen, no printouts. Bathroom breaks were monitored by Microsoft security guards,” The Wall Street Journal reported.

What did the evaluators find? “The programming manual was so disorganized as to be useless, they said. “It lacked any kind of heading or chapter organization, failed to define programming terms, and was so vast as to be more confusing that helpful.”

The evaluation lead EU regulators to threaten the software maker with fines—several million a day—until the manual was deemed acceptable. In order to meet the demands of the EU, Microsoft hired an external documentation consultant—Neil Barrett, a British computer scientist. After reviewing the documentation, Barrett agreed with the earlier criticisms of the Microsoft manual, and told The Wall Street Journal “The manual contained gibberish text, chapters that didn’t begin or end, and links to websites that led to nowhere.”

Barrett was also was quoted by ZDNet as saying: “Any programmer or programming team seeking to use the technical documentation for a real development exercise would be wholly and completely unable to proceed on the basis of the documentation. The documentation appears to be fundamentally flawed in its conception, and in its level of explanation and detail,” Barrett added. “Overall, the process of using the documentation is an absolutely frustrating, time-consuming and ultimately fruitless task.”

Read more about the EU Microsoft Anti-Trust issue.

On the other side of the Atlantic, things aren’t any better—at least not for Microsoft documentation. According to a report in MacWorld, “The U.S. Department of Justice (DOJ) asked a U.S. judge on Friday to extend parts of an antitrust order for Microsoft for at least two years because of the company’s delays in supplying technical documentation to licensees of its communications protocols.” At issue are numerous errors in the document—414 of them, to be exact.