So how did Microsoft get its bad reputation in the first place?
Well, anti-trust suits didn’t help their case, to be honest. Monopolizing any industry is a risky business, and throughout the 1990s in particular Redmond was suspected of playing very dirty to get the results they wanted, usually via acquisitions of smaller firms developing interesting technology. This is in part one of the reasons why Microsoft became known for clunky software that didn’t appear to be cross-compatible with their other applications.
Of course, stuffy, slightly superior-sounding PR (that read like it was written by a director and not a wordsmith) didn’t help Microsoft during this era. Fair enough, they were the market leaders, but even when faults were found in the operating system, vulnerabilities in the browser, etc., there was little in the way of apology. The phrase "It's not a bug, it's a feature" was often used to summarize Microsoft's responses to users' complaints. It was more than enough to see the company lampooned in a James Bond film for knowingly publishing bug-filled software.
We shouldn’t forget selling services that should have been free, either, such as Internet Explorer, or the ability to access a Microsoft Network (MSN) email account via Outlook Express. In the old days, if Microsoft could charge you, they would.
Portable technology was often late in coming to MS, and when it did the user interface was nothing to write home about. Windows Mobile was far too similar to the old Pocket PC platform with a ten year case of freezer burn, while Zune was excellent hardware and a good user interface that was then given to a marketing department that appears to have mistaken it for an electric toothbrush.
Then you’ve got the stuff that should have been so much better. Windows Vista is a key example, although this could possibly be identified as Microsoft’s watershed moment. Reaction to the operating system was so poor that they reissued it as Windows 7; the differences are largely superficial (give or take a few new features and better user access control) and yet the later OS is so much more popular. Or at least it was much, much less despised.