Windows 10 / Windows 95 Dual Boot?

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Hi everyone,

I am in the midst of a crisis (“crisis” meaning I’m really frustrated). I really hope someone has a solution for me.

We used to have an old computer the grand-kids used to play games, and a few months ago it finally bit the dust. I don’t remember which OS it was running, but all the old game disks we have say “Windows 95/Windows 98/Windows 98SE”.

My wife finally talked me into buying a new computer so our autistic granddaughter can play the games that she loved to play on the old PC. The one I bought is a decent used Dell that I got from a reputable local business. It came with Window 7 installed. This was really nice because I’ve had only a laptop for the last couple of years and I would now have a desktop I could use when the kids weren’t here.

Unfortunately, when I tried the old discs on it, very few of them would install. And yes, I did try all the emulation modes; they didn’t help.

Because the free Windows 10 deadline was rapidly coming up, I went ahead and installed it. I thought that whatever I might do to install Windows 95 would work as well under Windows 10 as under Windows 7.

My immediate solution (I thought) was to buy a copy of Windows 95 and install it on a virtual machine running under Windows 10. I downloaded VirtualBox and installed it, then installed a Windows 95 virtual machine in the machine manager. However, when I put the Windows 95 DVD in, nothing happened. I discovered that to install an OS to a VirtualBox machine, the OS disk needs to autoboot. The suggestion was made to install from floppy. I don’t have a floppy disk drive!

So I went to plan B. I’d just create a dual boot system to run either Windows 10 or Windows 95. However, in researching this, I read that unless I installed the older operating system first, it would screw things up, because, in this case, Windows 95 doesn’t how the way things are organized on the disk drive for Windows 10.

I do have backups, both before and after upgrading to Windows 10. Unfortunately, if I had to reinstall Windows 10 I wouldn’t be able to, because I didn’t save the installation files and the deadline has passed. The PC didn’t come with a Windows 7 installation disc, either.

Can anyone solve this dilemma for me? What would you do, short of just trashing Windows 10 and 7 and making the PC a Windows 95 PC that would only play the old games and not much else? I would be eternally thankful….

Thanks,
Keith

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Your inquiry covers several different issues, Keith: how to install Win95, how to dualboot, how to use VirtualBox, and why the old CDs wouldn’t install under Win7/10.

Let’s put some of those issues to bed right away: do not attempt to install Win95 on your new machine as a single or dualboot OS. It is unlikely to work. For one thing, Win95 could only support a maximum hard disk size of 8GB, and your machine’s hard disk is much larger than that. In addition, you’ll probably have great difficulty finding Win95 drivers for the new machine’s hardware.

(You didn’t say which model you bought, but you can do a driver check by going to support.dell.com and entering the Service Tag from the sticker on your machine, or alternatively, finding your model under “Browse for a product”. Click “Drivers & downloads” in the left pane, and “Change OS” in the right pane. The drop-down will show all Windows OS’s for which drivers are available. It’s quite unlikely you’ll find Win95 listed there.)

As to why the old CDs wouldn’t install under Win7 or Win10, it sounds like you probably have a 64-bit version (the most common) of Windows. Some software–principally, very old versions–won’t work on a 64-bit OS.

That leaves you with two choices for running very old programs on newish hardware: either continue pursuing the virtualization option you started on, or install a less old, 32-bit OS on your new machine. For instance, if the drivers check above shows XP drivers are available, there’s a much better chance your old software would work if you dualbooted with 32-bit XP rather than Win95.

(Well, okay, there’s a third choice: swap out your 64-bit Win7/10 for a 32-bit version. I wouldn’t consider that a palatable choice, however, and even if you did there’s still no guarantee the old software would work. It’s more likely to work, but that’s not a guarantee.)

Personally, I’d recommend seeing if you can make virtualization work first, as setting up a dualboot is not exactly a trivial process. VirtualBox can work. I use VB on my Win7/64-bit machine, and I run a number of old OS’s virtually, including DOS, Windows 98, 2000, and XP.

It sounds like you could use a primer, though, on how to use VB. For starters, there’s more to it than just sticking a Win95 CD in the drive, you have to also tell VB to capture the drive (i.e., tell the virtual guest machine to take control of the physical drive from the host machine). Did you also create a virtual hard disk (and remember the 8GB limit) for the virtual guest? If not, you need to do that so you have something on which to install the Win95 OS. From there, the actual procedure for installing Win95 on the guest will depend on whether your Win95 CD is a Full or Upgrade version.

For specific questions on how to use VB, you may find the VB forums (forums.virtualbox.org) helpful.

Perhaps these tips will help you narrow your focus on what direction you need to go.

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Thanks very much, dg. Sorry for the slow reply; I’ve had family visiting and haven’t had a chance to get back to this.

I hope you’re still around, because I do have several responses to some of your comments and suggestions.

Let’s put some of those issues to bed right away: do not attempt to install Win95 on your new machine as a single or dualboot OS. It is unlikely to work. For one thing, Win95 could only support a maximum hard disk size of 8GB, and your machine’s hard disk is much larger than that. In addition, you’ll probably have great difficulty finding Win95 drivers for the new machine’s hardware.

Thanks for this. It’s been so long since I’ve worked with Win95 I didn’t event think of the disk size limitation (obviously).

(You didn’t say which model you bought, but you can do a driver check by going to support.dell.com and entering the Service Tag from the sticker on your machine, or alternatively, finding your model under “Browse for a product”. Click “Drivers & downloads” in the left pane, and “Change OS” in the right pane. The drop-down will show all Windows OS’s for which drivers are available. It’s quite unlikely you’ll find Win95 listed there.)

I actually misspoke; it’s not a Dell. It’s an HP Compaq 8000 Elite, and so far at least, I haven’t been able to find any driver information at all at HP Support for this model.

Also, it’s been refurbished, and I don’t know what’s been replaced (without opening it up to check, which I haven’t done yet).

As to why the old CDs wouldn’t install under Win7 or Win10, it sounds like you probably have a 64-bit version (the most common) of Windows. Some software–principally, very old versions–won’t work on a 64-bit OS.

Actually, it’s a 32-bit PC, so that isn’t it.

That leaves you with two choices for running very old programs on newish hardware: either continue pursuing the virtualization option you started on, or install a less old, 32-bit OS on your new machine. For instance, if the drivers check above shows XP drivers are available, there’s a much better chance your old software would work if you dualbooted with 32-bit XP rather than Win95.

That’s an excellent idea. I might give it a try with XP and see if the games run.

Personally, I’d recommend seeing if you can make virtualization work first, as setting up a dualboot is not exactly a trivial process. VirtualBox can work. I use VB on my Win7/64-bit machine, and I run a number of old OS’s virtually, including DOS, Windows 98, 2000, and XP.

No, dual boot isn’t trivial. I have set it up a few times with Windows/Linux, and once or twice with two Windows versions, but that was years ago, and you’ve convinced me that there would likely be some issues with Win95.

I’m glad to hear that you’re successfully virtualizing some of the older Windows versions. Most if not all of these CDs should run under 98 or 2000, so I might end up buying one of those as well as 95.

It sounds like you could use a primer, though, on how to use VB. For starters, there’s more to it than just sticking a Win95 CD in the drive, you have to also tell VB to capture the drive (i.e., tell the virtual guest machine to take control of the physical drive from the host machine). Did you also create a virtual hard disk (and remember the 8GB limit) for the virtual guest? If not, you need to do that so you have something on which to install the Win95 OS. From there, the actual procedure for installing Win95 on the guest will depend on whether your Win95 CD is a Full or Upgrade version.

You’ve right about that. I have not used VirtualBox, so I can definitely use a primer. I don’t remember anything about capturing the drive during setup, but in Settings, Storage shows two devices: “Windows 95.vdi” and “Host Drive D:” (the CD-Rom drive). I am under the 8GB limit (accidentally). I’m lost as to where to go from here, though.

For specific questions on how to use VB, you may find the VB forums (forums.virtualbox.org) helpful.

Thank you. I’ll definitely check out the forums.

Perhaps these tips will help you narrow your focus on what direction you need to go.

Absolutely. Thanks again, and sorry for the epistle.

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If they are W95 games there is a chance they will work under DOSBox – this will run in any current Windows version without having to install another operating system.
What games are they?

cheers, Paul

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If they are W95 games there is a chance they will work under DOSBox – this will run in any current Windows version without having to install another operating system.
What games are they?

Thanks, Paul. I haven’t seen DOSBox mentioned for years and I didn’t think of using it but I’ll look into it.

The games are education, mostly pre-school or 1st grade level: Things like the JumpStart series, and Scholastic and Fisher Price games. Dora the Explorer used to be one of her favorites.

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…What would you do, short of just trashing Windows 10 and 7 and making the PC a Windows 95 PC that would only play the old games and not much else?…

I would install “BootItBM” boot manager from: http://www.terabyteunlimited.com/bootit-bare-metal.htm

Not free, but very good value-for-money. Includes partition management and “Image for DOS”.

With BootItBM installed on your HDD and configured correctly you could boot either Windows installation as if the other Windows installation was not there.

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I would install “BootItBM” boot manager from: http://www.terabyteunlimited.com/bootit-bare-metal.htm

Hi Coochin,

Thanks. I’ve actually owned BootIt NG for many years, but haven’t been using it lately.

I couldn’t find anything on the site about upgrading BootIt NG to BootIt Bare Metal. Do you know what their policy is?

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Hi Coochin,

Thanks. I’ve actually owned BootIt NG for many years, but haven’t been using it lately.

I couldn’t find anything on the site about upgrading BootIt NG to BootIt Bare Metal. Do you know what their policy is?

I’ve looked back through my records and it looks like I upgraded from BootItNG to BootItBM v1.16 some time in early 2013 for AU$20.79.

Have upgraded BootItBM as each new version was released (now at v1.33) and have not been asked for any further payment.

From memory I think I emailed support@terabyteunlimited.com and asked them how to upgrade.

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I’ve actually owned BootIt NG for many years, but haven’t been using it lately.

I couldn’t find anything on the site about upgrading BootIt NG to BootIt Bare Metal.

Just to be clear, BootIt-NG will work perfectly fine as a boot manager if you choose to dualboot. You don’t need to upgrade to BootIt Bare Metal. BIBM does have some nice features in its partition manager and disk imaging functions that make it worth the upgrade, but strictly speaking, it’s not required in your case.

Of course, BING vs BIBM is moot if you’re virtualizing instead of dualbooting.

It’s an HP Compaq 8000 Elite, and so far at least, I haven’t been able to find any driver information at all at HP Support for this model.[/quote]
Drivers are on HP’s site here. Looks like the oldest they’ve got is for XP, so that means you should have the option of dualbooting XP with 7/10 if you choose to go that way.

The fact the machine is refurbished shouldn’t matter. It’s unlikely refurbishment altered any of the hardware that is dependent on a driver.

I don’t remember anything about capturing the drive during setup, but in Settings, Storage shows two devices: “Windows 95.vdi” and “Host Drive D:” (the CD-Rom drive).[/quote]
Just for kicks, I created a temporary VM and went through the motions of installing Win95. The screenshot below shows where you need to capture your CD and floppy drives.

Like installing Win95 on real hardware, the installation process involves:

[*] create a virtual hard disk (which you’ve already done);
[*] fdisk or partition the virtual hard disk;
[*] format the virtual partition (with FAT16, as you won’t have FAT32 support unless you have Win95b);
[*] insert the Win95 CD (virtual or real) in the appropriate drive;
[*] boot from a DOS floppy or Win95 boot floppy (virtual or real), since the Win95 CD isn’t bootable;
[*] launch “r:setup” (or whatever drive letter your boot floppy gives to the CD drive;
[*] if it’s an Upgrade version of Win95, you’ll need to swap in your Win 3.1 floppies in the real or virtual drive when prompted.

When you launch the VM, look under “Devices”, select “CD/DVD Devices”, and choose the physical drive on the host where you inserted your Win95 installation CD. (Note: in my experiment I used a virtual CD–an iso image of a Win95 CD instead of a physical CD.) You’ll need to do a similar procedure to insert your boot floppy in “Floppy Devices”.

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You might try this page to be offered an upgrade to BootItBM.

Image or Clone often! Backup, backup, backup, backup......
- - - - -
Home Built: Windows 10 Home 64-bit, AMD Athlon II X3 435 CPU, 16GB RAM, ASUSTeK M4A89GTD-PRO/USB3 (AM3) motherboard, 512GB SanDisk SSD, 3 TB WD HDD, 1024MB ATI AMD RADEON HD 6450 video, ASUS VE278 (1920x1080) display, ATAPI iHAS224 Optical Drive, integrated Realtek HD Audio

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Thanks, Coochin, RockE and dg1261, for all the good information on BootIt BM. I searched through all my old email and was surprised to see that I had original ordered BING in 2001! Because I ordered with an email address I haven’t used for many years and can’t find my actual order email, I’ve had a hard time finding and entering my registration information and getting it sent to my current address. I find several old messages to and from David F. trying to sort it out. I think I’ve finally been successful, and have been offered any upgrade for UR $20.

dg, are you sure there are no issues using BIBM with Windows 10?

In any case, my main concern right now is to do my best to make things work in a virtual machine. I need to spend some time studying your latest message and following up on it. Thanks again!

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dg, are you sure there are no issues using BIBM with Windows 10?

I never said there aren’t any issues. You had mentioned you had BING but not BIBM, so my point was that BING, although old, is not incompatible with multibooting Win10. Either will work as a multiboot manager, but you’ll face the same Win10 issues either way.

Some of those issues include MBR-vs-GPT, dealing with SRP or MSR partitions (those optional, extra little partitions Microsoft likes to saddle you with), and disabling Win10’s “Fast Start” option, which is enabled by default.

Those issues can be dealt with, and me and many others here are successfully multibooting Win10 on our systems. But it all adds to why I stated setting up a multiboot is not trivial, especially with an OS that is already installed.

Hopefully, DosBox or virtualization will work for you and you won’t have to deal with multibooting.

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