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Installing Windows 95 on VirtualBox on MacOS

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Installing Windows 95 on VirtualBox on MacOS

Ever wondered what it'd be like to install Windows 95 these days? Take a trip down memory lane as we walk through installing Windows 95 on VirtualBox on a Mac!

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Looking through a stack of CDs and DVDs on the shelf on my desk, amongst many other things, I still have install CDs for Windows 95 and Windows 98. I wondered (as you do, well, maybe not everyone does) what it would be like to install 95 again from scratch, so created a new VM in VirtualBox and off I went. If you’ve come across any of my posts before you might remember I’ve installed all sorts of OSes under VirtualBox before, because, well why not? OS/2 and AROS probably the most interesting.

The steps in this blog are very useful for a guide. Windows 95 install CDs were apparently not bootable, and I don’t remember having boot floppies. If I did I probably don’t have them anymore. I download a Windows 95 boot disk floppy .img from here, and attached it to the floppy drive in the VirtualBox config for this machine.

After booting to an a: prompt, attempted ‘format c:’ but got a ‘invalid drive specification’ error. Seems I needed to partition my blank attached virtual disk first, so from the a: prompt, ran fdisk:

And then:

setup

Next, Windows 95 setup was telling me that my newly created and formatted disk was reporting an incorrect size, so started a Scandisk:

1GB or more.

I decreased it to 512MB, then got:

Other posts seem like this is to do with host CPUs faster than 2.1GHz, and my Mac Pro has dual 2.8 Xeons. Maybe this is as far as I’m going to get with 95. Next up, trying 98!

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Topics:
virtual ,virtualbox ,windows ,macos ,devops

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