Bill Gates tries to install MovieMaker (2003)

In January 2003, Bill Gates sent a frustrated email to Windows executives Jim Allchin, Chris Jones, and others, lamenting that Windows usability has 'been going backwards' and that program management groups ignore usability issues. To illustrate, he described his experience attempting to download MovieMaker and the Digital Plus pack from Microsoft.com.

Gates reported the download page timed out on five consecutive attempts before loading after an eight-second delay. When the page displayed a list of downloads, MovieMaker wasn't in the top 5 of the 50 items shown, and Gates found the names 'totally confusing' and not filtered by his system. Searching the page for 'moviemaker' and 'movie maker' returned nothing, so he emailed a colleague who explained the download page was never intended for direct downloads and instructed him to use the main page search with 'movie maker' (with a space). That search returned a slow, puzzle-like page directing him to Windows Update, where he was forced to download and install controls multiple times, then download 17 MB of 'critical' updates (despite claims of delta patches) with 'scary' labels. The install then took six minutes, rendered his machine unusable, and insisted on a reboot, which destroyed his Outlook session.

After rebooting and returning to Windows Update, the email stops, but the point was made: the process Gates endured was a maze of confusing names, unnecessary scans, and forced reboots — exactly the kind of systemic usability degradation he was complaining about. The email later surfaced publicly and became a classic illustration of usability problems within Microsoft's own download experience.

The email highlights how even the CEO of Microsoft couldn't easily navigate his own company's software, underscoring the gap between technical engineering and user-centric design. It's a reminder that usability failures are especially damaging when they occur at the very gateway to a company's products.