Windows ME was critically panned on release. It dropped many features from previous Windows versions, but did nothing to improve stability. I made an ISO from my old and scratched Windows ME disk, mounted it in Synology VMM and let it boot.
Start Windows Setup from CD-ROMStart Computer with CD ROM SupportMicrosoft Windows ME Setup
The boot screen sent me into throes of nostalgia. So did the next steps.
Windows Millenium Edition, enable Large Disk SupportFormatting Hard DiskWindows Millenium Edition, Microsoft ScanDisk, Checking File System
I could feel myself going crazy when the setup GUI came up; thankfully, the mouse & keyboard worked without any tinkering. The installation process and steps were quite similar to Windows 98.
Windows Millenium Edition SetupTo begin Setup, click NextWindows Millenium Edition, Preparing DirectorySelect the kind of setup you preferWindows Millenium Edition, Select Components
The whole process was much faster than Windows 98 SE, because VMs run natively on the Synology, which has official/proper Hypervisor support.
Windows ME, select Time ZoneReady to Begin Copying FilesWindows ME, Please sit back and relaxMore EntertainingWindows ME, Supports New HardwareThank you!
After the first reboot, I was presented with the famous “first time” Windows ME boot splash screen. Another huge dose of nostalgia.
Windows Millenium Edition Boot Screen
The second phase of setup has much different graphics compared to the first phase, a bit more bright & modern.
Windows ME is now initializing its driver databaseUser InformationWindows ME Setup, License AgreementClick Finish to complete SetupWindows ME Setup, Updating ShortcutsUpdating System SettingsWindows ME, Restart NowUpdating System Settings with drumroll
Signing up for Azure’s free tier was pretty painless (If you don’t count opening each link within their portal in a new tab). Although, a few terms are a bit technical and require doing a bit more research.
I chose the below starting specs for my parent VM:
Zone: Asia Pacific (Central India) OS: Windows Server 2022 Datacenter Edition CPU:2 vCores RAM: 8Gb Disk:HDD 32Gb, 500 IOPS, 60Mbps
*I chose Central India as the Datacenter, because I also wanted to use this VM to access Indian websites, geolocked outside India.
I used the Windows app to remote-in to the parent VM and installed Oracle Virtual Box to host my child VMs. Luckily, the Windows app supports transfer of files from the iPad to the VM, but it is painfully slow (400-700 KBps).
Slow file copy via the Windows iPad app
Eventually, I ditched this approach, because
The on-going costs were more than I was willing to spend on this project (Especially because there is no way to accurately predict how much you will be charged)
The software is quite powerful and except clustering, almost all the features are free.
However, the Hypervisor doesn’t seem to be optimised to run such old OSes. I could get the Windows 98 installation to complete, but I couldn’t get the OS to boot however much I tried.
It was safe to assume even older OSes like Windows 95 and Windows 3.1 would never work. So I gave up.
My Retro Computing plans are on hold for the time being.
Windows 98 SE was the first OS on my first computer, so this was a huge trip in nostalgia. I made an ISO from my old and scratched Windows 98 SE disk, mounted it in UTM SE and let it boot.
Windows 98 SE, Start Computer with CD ROM Support
The boot screen sent me into throes of nostalgia. So did the next steps.
Windows 98 Setup, Formatting Hard DiskMicrosoft ScanDisk, Checking File System
I could feel myself going crazy when the setup GUI came up.
Windows 98 Setup, To begin Setup, click Continue
I got stuck for a while here because I couldn’t make my keyboard and mouse work. Eventually, I figured out that I needed to disable support for USB peripherals and I could continue.
Setup is preparing the Windows 98 Setup WizardWindows 98 Setup Wizard, Select DirectoryWelcome to Microsoft Windows 98Windows 98 SE Setup, Easier to get HelpWindows 98 SE Setup, More Entertaining
After the first reboot, I was presented with the famous “first time” Windows 98 boot splash screen. Another huge dose of nostalgia.
Microsoft Windows 98, Getting Ready to run Windows for the first time
The second phase of the setup is (was) my favourite. I especially like the part with the beating drums animation.
Windows 98 is initializing its driver databaseIs Windows now detecting non Plug and Play hardware in my computer?Windows is now setting up the following itemsUpdating Shortcuts: ProgramsWindows 98 Setup, Updating System Settings
Eventually, after an hour and 50% of my iPad’s battery, setup was complete and it booted into Windows.
New Hardware Found, Standard Display Adapter (VGA)New hardware found, Default Monitor
Last week, something unthinkable happened. Apple finally allowed emulation of any and all OS on iOS and iPadOS. The intended purpose is to emulate retro Windows based games, which matches their recent trend of approval of gaming-system emulation apps. However, for me, it restarts a long-time hobby of running retro OSes purely for nostalgia and hobby purposes. This was not possible before because I don’t have a real computer, just an iPad. The first app to take advantage of this change of heart from Apple is UTM SE.
Now, UTM SE has been available on macOS and jailbroken iOS and iPadOS for quite some time, but this is the first time the app is officially available through the App Store.
Overview
The process to configure a new VM is much like most virtualisation apps out there. You use either an existing image or create a new one, select various parameters like RAM, HDD, CPU architecture, cores etc.
UTM SE: New VMUTM SE: Mount CD/DVD or Floppy imageInside UTM SE: Select Platform, CPU architecture, RAM and CPU CoresUTM SE: Select HDD Size
Your Bluetooth mice/keyboards can be mapped to the guest OS via USB or PS/2 emulation. For older OS (Pre Windows ME) which don’t have out of-box support for USB peripherals, you need to disable USB support for Mouse/Keyboard so that they are emulated as PS/2. Even touch gestures can be used in lieu of a mouse, although the experience is clunky.
UTM SE: Switch between USB or PS/2 for mouse and keyboard
Another useful feature is that you can map a folder on your iOS/iPadOS filesystem to the guest machine allowing you to transfer files easily.
Select Shared Directory
Also, you can choose to include your VMs in your iCloud backups.
For me, the performance is roughly similar to my first Celeron 400Mhz computer. Which, when compared to the 4×3.49Ghz high-performance cores on the Apple M2 means there is an approx 35x performance penalty for emulation. No wonder the “SE’ in UTM stands for “Slow Edition”.
Also, switching to another app causes UTM to suspend the VM after a few minutes. None of this is UTM’s fault, but needless restrictions from Apple to stop iPads from cannibalising Mac sales.
Also, the iPad screen locks after inactivity, which I think is on UTM, because apps (especially games) have been able to keep the screen unlocked through inactivity.
But the good thing is, you can resume from where you left off. Also, you can run multiple windows of UTM itself, even with multiple windows mapping to multiple monitors on the guest.
Battery usage is also extremely high because of the inefficiencies.
