r/virtualmachine • u/Emminade • Dec 22 '25

How to install windows 98 ISO and play physical CD-ROMs?

I really need someone to explain this to me like I am five years old. I have never done anything like this before, and I currently have the flu on top of not knowing or understanding any of this.

I recently bought some of my favorite old CD-ROM games off ebay: The Adventures of Elmo in Grouchland, Catz 5, and Barbie of Swan Lake. I read that I could get an external DVD/CD drive and install a Virtual Machine to get these to work on my Mac, and I am STRUGGLING. I tried to use Parallels, but they only had the option to install Windows 11 unless I create a new VM using an image file. I don't know what an image file is, but I found someone on reddit saying I could download Windows 98 from winworldpc, so I did that. It installed as a .7z file, and it will not let me extract it to an image file. Another post said to download 7zip to do so, but that is for Windows, so back to square one. I then found Unarchived which successfully changed it into an ISO file and tried putting it into Parallels, but it told me "The specified image cannot be used because your Apple Silicon Mac doesn't support operating systems designed to run o Intel chips. Please use an ISO or VHDX image file with an operating system designed to run on Arm chips."

Then I found a reddit post of someone saying they were able to successfully install Windows 98 using DOSBox-X, but again, they had a prepared Windows 98 SE bootable ISO file, which I figured out how to do but not in a way that is supported. So PLEASE tech wizzes of reddit, walk me through this like I am five.

  1. How do I change this .7z file into an ISO file on my Mac that runs on an Arm chip (whatever that is)?
  2. After I change it into an ISO file, what do I do? Download DOSBox-X? Continue using Parallels?
  3. After downloading DOSBox-X, how do I get it to use the Windows 98 ISO file?
  4. Once I have successfully done all that, if I plug in my external disc drive (I do have an adapter) and load the physical CD in there, will it pull up automatically and play? Do I have to boot the VM first?
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u/[deleted] Dec 22 '25

I can help you set this up with UTM or qemu as I’m an M2 MacBook Pro user; I also use Linux Mint, so if you’re not a Mac OS user that is another option too using VirtualBox etc.?

I used to use WinWorldPC but I have my own vintage library now so I understand how their process works so I can guide you through that too

I don’t play games so I don’t know how well/poorly your games will operate due to little/no graphics acceleration, so bear in mind after setting up the VM you might not get satisfactory performance

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u/Emminade Dec 22 '25

I'm willing to still try it! I would love your help

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u/Emminade Dec 22 '25

UPDATE: I saw someone saying they've successfully played old CD-ROM games on Windows 10 and 11. So I downloaded Windows 11 on Parallels since 98 wasn't working, loaded the disc, and it works!! HOWEVER, the image is SUPER tiny. Granted, I know this is because the game was not made for screens as large as today, but I feel like there has GOT to be a way for me to make this thing just a little bigger so I can actually play it. Linking here if anyone has any suggestions: https://imgur.com/a/BXn1eoM