Pushing the boundaries of operating system flexibility has long been a point of pride for Windows enthusiasts. Over decades, Microsoft’s desktop platform has earned a reputation for not only powering modern hardware and productivity workloads but also for its backwards compatibility and malleability. Nowhere is this brilliance and chaos on display more clearly than in the art of Windows virtualization. While enterprise IT departments rely on virtual machines (VMs) for managing server sprawl or creating secure sandboxes, for adventurous users and digital historians, VMs become an avenue for reliving the eccentricities of decades-old Windows environments, experimenting with software long past its support date, or executing technical stunts simply because it seems impossible. In the creator-driven landscape of YouTube, a recent project went viral for its audacious scope: running Windows—inception-style—layer upon layer, to simulate an operating system nesting doll that pushes both logic and silicon to their limits.
Since the advent of Hyper-V, VMware Workstation, VirtualBox, and other hypervisors, virtual machines on Windows have opened up possibilities for enterprise administrators, enthusiasts, and hobbyists alike. Rather than being limited to a single OS instance per device, VM software allows for operating system “containers,” complete with network, storage, and a virtualized set of hardware resources. Windows, in particular, is a fertile playground for this experimentation because it still supports a range of legacy applications, drivers, and tools—features that power users and organizations often rely upon. Furthermore, as newer editions of Windows have become more locked down in certain respects, virtualization provides a means to escape modern limitations and dive into old-school software ecosystems, from DOS-based Windows 3.1 up to Windows Vista and beyond.
But with every leap in flexibility comes challenges. From hardware compatibility inconsistencies and poor driver support to mounting security risks and the ever-present drag on performance, VMs live in a delicate balance between isolation and resource consumption. Nonetheless, this duality is what draws a steady crowd of digital tinkerers into the rabbit hole—with bruises and strange discoveries along the way.
The ultimate challenge: run Windows 95 inside Windows 98, inside Windows 2000, inside Windows XP, inside Windows Vista, inside Windows 7, inside Windows 8.1, inside Windows 10—all cohabiting within a parent instance of Windows 11. As daunting as that sounds, the utility of such a setup is secondary to sheer curiosity. Could Minecraft Classic, for example, be made to run within this virtual Rube Goldberg machine? Just how deep does performance and compatibility collapse as you descend through the OS layers?
For the experiment, built-in Hyper-V was initially the hypervisor of choice. Hyper-V is tightly integrated into modern Windows 10 and 11, praised for its speed and security. However, as became painfully obvious, even Microsoft’s own hypervisor struggled with the demand: after nesting just three OS layers—Windows 8 inside Windows 10 inside Windows 11—the setup collapsed. Hyper-V refused to cooperate further, failing to handle the deep virtualization required to emulate ever-older hardware beneath multiple stacks of recent Windows software.
Still, the process was far from seamless. Systems like Windows 7, when installed inside Windows 8 (itself inside Windows 10 and so forth), demonstrated how severe the performance hit could be. In the experiment, Windows 7 took a staggering 30 minutes to progress through a basic boot cycle, emphasizing how dearly the VM stack exacts its toll as each new layer adds more abstraction and latency.
At this point, the notion of serial nesting—each successive VM inside the previous layer—became unworkable. The creator switched to a “parallel virtualization” approach, running two separate VMware instances on the Windows 11 host. In one, Windows 10 would run Windows 8, which ran Windows 7. In the other chain, Windows Vista would host Windows XP, which in turn would nest Windows 2000, and finally, Windows 98. Attempts to install Windows 95 at the very bottom of this well led only to endless stalls: Windows 98 simply wasn’t stable enough to complete the next installation. Every layer magnified resource constraints and hardware compatibility issues, resulting in startup times that often felt longer than the lifespan of the OSes themselves.
Performance was, predictably, best within the main Windows 11 install, where hardware acceleration and modern APIs are available. As the layers increased, however, the toll did not scale linearly but exponentially: by Windows 10 and Windows 8, frame rates had already dropped by over 50%. Minecraft Classic became unplayable in Windows 7 buried in this virtual latticework, with input delays and frame pacing issues impossible to ignore. The deeper, parallel stack—ending with Windows 98—exhibited similar patterns, with performance cratering long before reaching the truly ancient operating systems.
Such results underline a core paradox in virtualization: while compatibility layers have come a long way, each new abstraction removes the software further from the bare metal. Tasks that are trivial for a lightweight DirectX 8 or OpenGL game in the native host become Sisyphean chores for deeply nested guests, especially when compounded by legacy driver models, old DirectDraw implementations, and the peculiarities of early hardware acceleration.
However, deep nesting remains a fringe activity, unsupported in any official documentation and frequently at odds with both hardware and hypervisor design. Mainstream hypervisors like Hyper-V are streamlined for two or three layers—host, guest, perhaps a nested guest—and anything beyond is a trip into the unknown. VMware remains a favorite among legacy aficionados for its willingness to compromise on speed in favor of compatibility, but even it can only go so far. The MetraByte video is therefore not just a technical curiosity but also a cautionary tale, reminding even the most intrepid users of the hidden barriers that virtualization, however magical, cannot always breach.
The use case is different, but the lessons are parallel: isolation offers safety, flexibility, and resource sharing, but always at a cost—sometimes trivial, often steep, both in latency and dollars. Meanwhile, the rise of containerization (think Docker and Kubernetes) offers an alternative, sandboxing at the application rather than system level. Yet, for full OS nostalgia or legacy compatibility, virtualization reigns supreme.
For Microsoft, there is subtle reassurance: that even as Windows marches onwards, leaving behind older hardware and software, there remains an enthusiastic, technically savvy community ready to keep those memories, and that software, alive in digital amber. For the rest of us, these tales from the bleeding edge spark a valuable perspective—reminding users and IT pros alike that every OS, no matter how obsolete, can still be conjured up given patience, the right tools, and a sense of wonder.
The next time you grumble about your computer being “slow,” remember: somewhere, someone is booting Windows 98 inside a digital labyrinth of their own making, just to see if they can—because Windows, for all its flaws, remains the most intriguingly hackable ecosystem in computing history.
Source: XDA Developers Windows was never meant to run this way, but someone made it happen
Since the advent of Hyper-V, VMware Workstation, VirtualBox, and other hypervisors, virtual machines on Windows have opened up possibilities for enterprise administrators, enthusiasts, and hobbyists alike. Rather than being limited to a single OS instance per device, VM software allows for operating system “containers,” complete with network, storage, and a virtualized set of hardware resources. Windows, in particular, is a fertile playground for this experimentation because it still supports a range of legacy applications, drivers, and tools—features that power users and organizations often rely upon. Furthermore, as newer editions of Windows have become more locked down in certain respects, virtualization provides a means to escape modern limitations and dive into old-school software ecosystems, from DOS-based Windows 3.1 up to Windows Vista and beyond.But with every leap in flexibility comes challenges. From hardware compatibility inconsistencies and poor driver support to mounting security risks and the ever-present drag on performance, VMs live in a delicate balance between isolation and resource consumption. Nonetheless, this duality is what draws a steady crowd of digital tinkerers into the rabbit hole—with bruises and strange discoveries along the way.
Seven Layers Deep: The MetraByte YouTube Experiment
A recent viral video by the MetraByte channel exemplifies both the magic and madness that VMs can unleash on Windows. The experiment’s premise was simple but ambitious: how many layers of Windows could be run inside one another using nested virtual machines? Think Russian dolls, but each subsequent layer is a full-blown operating system, complete with its own graphical interface and, ideally, the ability to (barely) function.The ultimate challenge: run Windows 95 inside Windows 98, inside Windows 2000, inside Windows XP, inside Windows Vista, inside Windows 7, inside Windows 8.1, inside Windows 10—all cohabiting within a parent instance of Windows 11. As daunting as that sounds, the utility of such a setup is secondary to sheer curiosity. Could Minecraft Classic, for example, be made to run within this virtual Rube Goldberg machine? Just how deep does performance and compatibility collapse as you descend through the OS layers?
The Hardware Foundation: Power Amid Limitations
Any attempt to nest this many operating systems lives or dies by the underlying hardware. The MetraByte video’s host used a Geekom IT-15 Mini PC—a modern but compact system packing an Intel Core Ultra 9285H processor. While this CPU is no slouch, it’s also not a full workstation-class behemoth. However, such an experiment is less about raw 3D rendering or multi-threaded performance and more about RAM, I/O subsystems, and the virtualizability of the system’s instruction set.For the experiment, built-in Hyper-V was initially the hypervisor of choice. Hyper-V is tightly integrated into modern Windows 10 and 11, praised for its speed and security. However, as became painfully obvious, even Microsoft’s own hypervisor struggled with the demand: after nesting just three OS layers—Windows 8 inside Windows 10 inside Windows 11—the setup collapsed. Hyper-V refused to cooperate further, failing to handle the deep virtualization required to emulate ever-older hardware beneath multiple stacks of recent Windows software.
Switching to VMware: When the Official Tools Can’t Cut It
Rather than giving up, MetraByte pivoted to VMware—a hypervisor with a long history of supporting advanced and exotic setups on x86 and x64 hardware. VMware’s compatibility and flexibility in simulating legacy peripherals and BIOS/UEFI quirks often outperform Microsoft’s own solution, especially for older operating systems.Still, the process was far from seamless. Systems like Windows 7, when installed inside Windows 8 (itself inside Windows 10 and so forth), demonstrated how severe the performance hit could be. In the experiment, Windows 7 took a staggering 30 minutes to progress through a basic boot cycle, emphasizing how dearly the VM stack exacts its toll as each new layer adds more abstraction and latency.
At this point, the notion of serial nesting—each successive VM inside the previous layer—became unworkable. The creator switched to a “parallel virtualization” approach, running two separate VMware instances on the Windows 11 host. In one, Windows 10 would run Windows 8, which ran Windows 7. In the other chain, Windows Vista would host Windows XP, which in turn would nest Windows 2000, and finally, Windows 98. Attempts to install Windows 95 at the very bottom of this well led only to endless stalls: Windows 98 simply wasn’t stable enough to complete the next installation. Every layer magnified resource constraints and hardware compatibility issues, resulting in startup times that often felt longer than the lifespan of the OSes themselves.
The Minecraft Classic Stress Test: When Vintage OS Meets Modern Gaming
To bring the experiment to life for viewers, MetraByte ran Minecraft Classic—a lightweight but graphically capable game with roots in the earliest days of indie gaming. Minecraft Classic is not resource-intensive by modern standards, but when force-fed through a gauntlet of virtual machines, it becomes a stress test worthy of academic study.Performance was, predictably, best within the main Windows 11 install, where hardware acceleration and modern APIs are available. As the layers increased, however, the toll did not scale linearly but exponentially: by Windows 10 and Windows 8, frame rates had already dropped by over 50%. Minecraft Classic became unplayable in Windows 7 buried in this virtual latticework, with input delays and frame pacing issues impossible to ignore. The deeper, parallel stack—ending with Windows 98—exhibited similar patterns, with performance cratering long before reaching the truly ancient operating systems.
Such results underline a core paradox in virtualization: while compatibility layers have come a long way, each new abstraction removes the software further from the bare metal. Tasks that are trivial for a lightweight DirectX 8 or OpenGL game in the native host become Sisyphean chores for deeply nested guests, especially when compounded by legacy driver models, old DirectDraw implementations, and the peculiarities of early hardware acceleration.
Beyond the Challenge: What Does Extreme Virtualization Actually Reveal?
MetraByte’s marathon is not simply an idle showcase; it offers profound insights into how Windows virtual machines function, the legacy layers they obscure, and the hard physics limits of abstraction. The project highlights several key strengths and weaknesses in modern virtualization.Notable Strengths
- Backward Compatibility: The fact that Windows 98, released over 25 years ago, can even boot (albeit slowly) within a virtual environment emulating a teetering stack of newer Windows OSes is a feat of both Microsoft’s legacy support and VM software engineering.
- User-Driven Customization: VMs remain a definitive method for tinkerers and power users to test software, simulate business workflows, or resurrect vintage applications without risking their main OS. For programmers, researchers, and debugging heavyweights, this flexibility is invaluable.
- Education and Experimentation: Virtualization offers a low-risk sandbox to demonstrate, study, or teach the evolution of operating systems. Historians, IT instructors, or even curious students can spin up a world of computing history in a few file downloads.
- Security Isolation: While not foolproof, properly configured VMs provide layers of defense against ransomware, exploits, and other malware. Enterprises exploit this to mitigate lateral movement and contain breaches.
Serious Drawbacks and Limitations
- Exponential Performance Costs: As shown by Minecraft Classic’s meltdown within multiple nested VMs, every extra layer means a geometric increase in latency and a corresponding drop in usable hardware resources. Eventually, a point of unusability is reached long before technical limits are truly tested.
- Complex Driver/Hardware Emulation: Legacy operating systems frequently expect real-mode drivers, specific chipsets, or features (such as pre-PnP hardware or standard VGA). Even the best VM programs struggle to bridge the gap, leading to crashes, lockups, and boot failures.
- Security Holes in Legacy OSes: Windows 98 or 95 running in a modern VM is unpatched, fundamentally insecure, and exposed to even the oldest forms of malware. While risk is contained within the VM, network exposure or misconfiguration can spill over into the host in rare cases.
- Time Investment: As MetraByte’s failed boot attempts and hour-long experiments demonstrate, even experts with the right hardware can run afoul of unpredictable errors, arcane troubleshooting, and wasted hours.
How Far Has Virtualization Really Come on Windows?
The experiment underscores both the remarkable progress the Windows ecosystem has made with virtualization—and the natural limits that remain. Early attempts at running virtualized OSes, such as the archaic “Virtual PC for Windows” or the short-lived Windows XP Mode in Windows 7, were awkward, limited, and barely supported hardware acceleration. Today, hardware virtualization via Intel VT-x, AMD-V, and related features allows better resource sharing and paravirtualization, smoothing out many wrinkles in guest OS performance.However, deep nesting remains a fringe activity, unsupported in any official documentation and frequently at odds with both hardware and hypervisor design. Mainstream hypervisors like Hyper-V are streamlined for two or three layers—host, guest, perhaps a nested guest—and anything beyond is a trip into the unknown. VMware remains a favorite among legacy aficionados for its willingness to compromise on speed in favor of compatibility, but even it can only go so far. The MetraByte video is therefore not just a technical curiosity but also a cautionary tale, reminding even the most intrepid users of the hidden barriers that virtualization, however magical, cannot always breach.
Potential Use Cases: Serious Functions and Fun Experiments
While running Windows 98 inside a stack of half-a-dozen newer operating systems is mostly an exercise in digital bravado, virtualization has very real and enduring use cases that thrive in the Windows ecosystem:- Software Testing/Development: Developers rely heavily on VM snapshots to test patches, upgrades, and cross-version compatibility without risking their main system.
- Malware Analysis: Security researchers use isolated VM sandboxes to dissect threats and simulate exploits.
- Business Legacy Support: Companies maintaining bespoke tools for Windows XP or NT4-era workflows can keep them alive longer, safely air-gapped.
- Historical Research: From retro-gaming communities to archival IT research, VMs offer a living museum of software and digital culture.
Risks and Caveats: Know Before You Dive In
Despite the fun, virtualization carries real risks if approached without caution:- Licensing and Activation: Running old Windows versions still requires legitimate licenses—even software now classified by Microsoft as abandonware may not be legally free for all uses. Ignore warnings of licensing expiration at your own peril.
- Security Concerns: Virtualized legacy OSes remain alarmingly vulnerable—especially if the VM is granted internet or local network access. Malware that infects an old instance can sometimes, through guest-to-host vulnerabilities or misconfigured shares, impact the host as well.
- Backup and Recovery: As with physical hardware, VM data should be regularly snapshotted and backed up to prevent data loss from accidental corruption, misconfiguration, or host crashes.
- Resource Contention: On resource-constrained PCs or laptops, running even one VM can severely hamper host performance—stacking multiple deep can make a system nearly unresponsive. Always monitor physical memory, disk, and CPU usage.
The Bigger Picture: Virtualization’s Other Frontiers
While MetraByte’s nested Windows marathon is a feat in itself, the evolution of virtualization is not confined to desktop playfulness. The rise of cloud computing—Microsoft’s own Azure, Amazon’s AWS, Google Cloud—relies on hypervisors far more advanced but philosophically related to desktop VMware and Hyper-V. Enterprises spin up thousands of Windows and Linux VMs per second, running workloads for everything from AI model training to none-too-glamorous payroll apps.The use case is different, but the lessons are parallel: isolation offers safety, flexibility, and resource sharing, but always at a cost—sometimes trivial, often steep, both in latency and dollars. Meanwhile, the rise of containerization (think Docker and Kubernetes) offers an alternative, sandboxing at the application rather than system level. Yet, for full OS nostalgia or legacy compatibility, virtualization reigns supreme.
Conclusion: When Limits Become the Playground
Running Windows inside Windows inside Windows may never become a mainstream trend—nor was it ever meant to. It’s a feat born out of curiosity, technical prowess, and a fair bit of stubbornness. The strengths of virtualization—flexibility, safety, backward compatibility—shine brightly, even as the pitfalls of exponential resource demands and arcane configuration issues serve as sobering reminders of the limits in play.For Microsoft, there is subtle reassurance: that even as Windows marches onwards, leaving behind older hardware and software, there remains an enthusiastic, technically savvy community ready to keep those memories, and that software, alive in digital amber. For the rest of us, these tales from the bleeding edge spark a valuable perspective—reminding users and IT pros alike that every OS, no matter how obsolete, can still be conjured up given patience, the right tools, and a sense of wonder.
The next time you grumble about your computer being “slow,” remember: somewhere, someone is booting Windows 98 inside a digital labyrinth of their own making, just to see if they can—because Windows, for all its flaws, remains the most intriguingly hackable ecosystem in computing history.
Source: XDA Developers Windows was never meant to run this way, but someone made it happen