Windows 3.x with VMWare Workstation Player

An earlier post, Install & Configure MS-DOS 6.22 & Windows 3.1 using Oracle VirtualBox has proven to be relatively popular since it was published. The intention was to create a similar guide using VMWare’s free Workstation Player 12.5.6 but alas usability wasn’t satisfactory enough that I felt creating one was warranted. Nevertheless here’s how the installation experience went. Cue the 1978 Split Enz song ‘I See Red’.

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Install & Configure IBM OS/2 Warp 4.52 Using Oracle VirtualBox

os2-45-1OS/2 initially developed in cooperation between Microsoft and IBM back in the 1980s had a turbulent history over the years. By 1996 with the final retail release of OS/2 Warp 4.0, IBM conceded defeat by Microsoft realising it was not able to compete with Windows 95, although still managed to withhold a portion of the enterprise market. Years later it was still found on some servers and even ATMs on the street.

OS/2 Warp 4.52 was the final version by IBM released in 2001 with official support ending in 2006. It wasn’t offered in a retail package, but for those who had a contractual agreement with IBM for OS/2 support. After this the foundation of the OS had evolved into what is now known as eComStation.

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Introduction to PCem (Version 11)

intel-386dx-25cpuPCem I personally believe is one of the more interesting hypervisors available to emulate hardware. Originally released in 2007 when it was limited to emulating an original IBM XT, PCem now allows for a Pentium PC running Windows 98 or even Windows XP.

Usually hypervisors for the most part have rather limited flexibility of the type of hardware that can be emulated. For example Oracle’s VirtualBox allows you to change the amount of video memory, but you’re unable to change from one model of video card to another. PCem gives you such options. Granted it’s not immediately obvious to the average Joe setting it up and getting it to work smoothly. Before focussing on how to set up specific operating systems, this will be an introduction on PCem in general based on creating a 386 PC.

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Install & Configure Windows NT 3.1 Using Oracle VirtualBox

Once the partnership with IBM faltered with the development of OS/2, Microsoft went alone and Windows NT was born back in 1993. Microsoft’s first true 32-bit operating system, it generally was to be seen only on high-end desktop workstations and servers. The first version was 3.1, to match the versioning of the more consumer orientated Windows 3.1 that was released a year prior. There was two editions – one named simply Windows NT 3.1 for workstation use, and the other named Windows NT 3.1 Advanced Server which obviously suggests for servers on a network. A relative lack of 32-bit software and higher system requirements meant success was limited and most of the attention was towards MS-DOS and Windows 3.1.

Installing Windows NT 3.1 is certainly not the easiest Windows to install into VirtualBox due to a few limitations. It’s very easy for the VM to crash or for NT 3.1 to complain about the hardware due to what was available at the time. Back then, Intel had been beta testing their new Pentium processors to supersede the 486, and introduced the CPUID instruction set which allows software to identify the CPU’s features.


By default, it’s a no go when installing unless Setup detects specific 386, 486, or Pentium processors.

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Install & Configure Windows 95 Using Oracle VirtualBox

Unlike my previous post, setting up Windows 95 is considerably different. Again I’ll be using Oracle VirtualBox 5.1.4. While it can be made to work in a useable state, it wasn’t offered the same support to the likes of Windows NT 4.0 or 2000.


There were a few revisions of Windows 95 since product launch generally offered for the OEM market, the latest being OSR 2.5. My personal preference is OSR 2.1 as it didn’t come preloaded with Internet Explorer 4.0, which had a tendency to bloat the general Windows interface with web orientated options akin to Windows 98. OSR 2.1 came instead with Internet Explorer 3.0 which kept to itself and more inline with the original Windows 95 interface. Not only that but I found IE 4.0 on real hardware of the time (e.g. a Pentium 100 with 16MB RAM) to be fairly sluggish in comparison.

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Install & Configure MS-DOS 6.22 & Windows 3.1 using Oracle VirtualBox

Installing DOS and Windows 3.x is relatively straightforward, though configuring both to perform the best they can can be a little more tricky. For this guide I’m using Oracle VirtualBox 5.1.4 (the latest at the time) on a Windows 10 machine. VirtualBox isn’t my first preference for emulation, however it’s free to obtain.


Windows 3.1 wasn’t technically an operating system in itself, though common perception is that it was. Unlike newer versions, Windows up to version 3.x would typically sit on top of some variation of DOS such as MS-DOS or PC-DOS which was the operating system.

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