On August 24, 2025, people celebrated the 30th anniversary of Windows 95, the operating system that first introduced the now-familiar Start menu. However, many Windows 11 users are frustrated with its complicated design, a problem similar to those experienced with earlier versions.
Microsoft engineer Raymond Chen recently shared that while Windows 95 *could* display graphics, the design team deliberately chose a simple, text-based interface. He explained that the graphics capabilities at the time were basic and they were working under a tight deadline.
A long-time Microsoft engineer recently explained in his blog series, The Old New Thing, why the original Windows 95 installation didn’t include a smaller, earlier version of itself. This allowed the setup program to be written as a fully functional 32-bit application.
Many people don’t realize the Windows 95 setup involved three separate programs running on different operating systems. If you started the installation from MS-DOS, the first program would launch, and it would then install a small version of Windows 3.1 to continue the process.
Chen further explained:
The installation process had two main programs. The first, a 16-bit Windows program, launched when upgrading from Windows 3.1 or a previous Windows 95 version and handled the bulk of the installation. The second was a 32-bit Windows program that ran *within* the newly installed Windows 95 to complete the final setup tasks.
Some users wondered if they could install a smaller version of Windows 95 on older systems running MS-DOS or Windows 3.1, instead of the usual Windows 3.1. They hoped this would allow the system to run more like a 32-bit operating system and take advantage of Windows 95’s improved capabilities.
The engineer explained that this approach wouldn’t have worked well for users or the development team. It would have required them to create a simplified version of Windows 95 just to make it feasible.
Because a thoroughly tested, small version of the operating system was already available, it was logical to build upon Windows 3.1. Chen also mentioned that the team was already falling behind on the Windows 95 development timeline.
Creating a small version of Windows 95 would have been a huge undertaking for Microsoft, especially since the operating system was still being developed. Chen explained that the request faced constant resistance, with people repeatedly asking, “Can we find a faster and cheaper solution?”
Although it was technically possible to create a tiny version of Windows 95, making it actually *work* well would have been difficult, and it likely wouldn’t have fit on a standard floppy disk. This is why Windows 3.1 was a more practical choice. Surprisingly, some skilled developers have managed to shrink Windows 95 down to just 7.5 MB in size.
There’s a slight complication: we need to create two separate sets of instructions for installing the tiny Windows 95, depending on where the process begins. This means repeating some code, and it’s a bit more involved than how Windows 95 itself copied the smaller Windows 3.1 version, because it requires switching between floppy disks.
Microsoft veteran engineer, Raymond Chen
A frustrating problem was that the system needed to be restarted twice. First, it would load a small, simplified version of Windows 95, and then finally boot into the complete Windows 95 operating system.
According to Raymond Chen, the ideal installation process for Windows would have quickly guided users to customize their setup, then handled the installation in the background, finishing with a single restart. Thirty years after Windows 95 revolutionized personal computers, its influence is still felt today. Chen’s stories highlight that even groundbreaking software relies on practical solutions and careful planning.
Many Windows 11 users are finding the new interface challenging, and are longing for the simpler, more user-friendly designs of the past. This isn’t just about feeling nostalgic – it’s a reminder that Windows 95 was so groundbreaking because it was clear, easy to use, and focused on the user. It remains to be seen if Microsoft can bring that same approach to future updates.
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2025-10-01 17:23