On August 24, 2025, tech enthusiasts commemorated three decades since Windows 95’s debut—ushering in the now-ubiquitous Start menu. Yet, dissatisfaction looms over Windows 11, as users grapple with its convoluted interface, echoing concerns that date back to its predecessor.
Earlier this year, veteran Microsoft engineer Raymond Chen revealed that although Windows 95 supported graphics, the company opted for a lackluster user interface dominated by dull text. He noted that the operating system’s graphical capabilities were primitive and constrained by time limitations.
Microsoft would’ve had a long day at the office making a miniature version of Windows 95, considering that it was still in the development phase. Chen indicated that this would have been an enormous ask, consistently getting pushback. “Can you find a quicker and less expensive way of doing this?” the engineer added.
One catch is that we have to write two versions of the code that copies the miniature Windows 95 to the system, depending on the starting point. That is a little bit of code duplication, and it’s a little more complex than the file copying code that Windows 95 actually uses for copying the miniature Windows 3.1 since there is a floppy swap involved.
Microsoft veteran engineer, Raymond Chen
There was also the reboot issue, which would require the user to go through the daunting task twice. The first one to boot into the miniature version of Windows 95 would allow you to access the full-fledged Windows 95 Microsoft operating system.
“The preferred workflow would be to get the user quickly to the point where they are answering questions about how they want Windows to be installed, and then go off and do the work and then finish in Windows 95 with a single reboot,” concluded Chen.
Three decades after Windows 95 reshaped personal computing, its legacy continues to echo through every Start menu click and every modern OS debate. Raymond Chen’s behind-the-scenes insights remind us that even the most iconic software is built on compromise, constraint, and clever engineering.
As users wrestle with Windows 11’s evolving interface, the nostalgia for simpler workflows and more intuitive design isn’t just sentimental—it’s a call to remember what made Windows 95 revolutionary in the first place: clarity, accessibility, and a user-first mindset. Whether Microsoft can recapture that spirit in its future updates remains to be seen.
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