Installing Windows 95 on VirtualBox on MacOS

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:

entered ‘y’ for large disk support, and then selected option 1 for ‘Create a DOS partition’ and then ‘Create Primary DOS partition’. Next, formated it:

format c:

then change to R: (the attached CD Drive)

and then


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

After this completed it still gave the same error, so I skipped this step:

Unfortunately at this point the install fails, and says the issue must be fixed before it will continue.

Possibly my 20GB attached virtual disk is not supported (too large), so reading around, it looks like a 2GB install disk is a supported size, so I was about to delete the 20GB disk and started again, but quitting the Scandisk before it completes with an error puts you back in the installer, and off it goes:

Some of the info screens during the install are rather interesting, promoting Window 95’s ‘high performance’:

“High-quality multimedia performance will dazzle you” – who wrote this stuff?

Who remembers dial-up MSN?

And then it fails ‘insufficient memory’ when booting up which is odd because I set the VM up with 1GB:

From post here and others, this seems this might be to do with having too much RAM configured for the VM, and in particular 1GB or more.

I decreased it to 512MB, then got:

This error on booting Windows 95 under VirtualBox seems related to VT-x virtualization. I can’t find the option to turn off VT-x support on my VirtualBox install, and 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 :-0

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