The integration of Linux and Windows Server environments has come a long way and Windows Subsystem for Linux (WSL) is at the forefront of this evolution. Though not brand new, WSL is still a powerful feature in Windows Server 2019, offering IT professionals the best of both worlds. In this guide, we’ll explore what WSL is, why it’s useful, how to install it, and real-world scenarios where it shines.
What is Windows Subsystem for Linux (WSL)?
Windows Subsystem for Linux (WSL) is one of the most impactful developments in bridging the gap between Linux and Windows Server environments. It is a compatibility layer developed by Microsoft that allows you to run native Linux binaries and command-line tools directly inside a Windows environment without the need for resource-heavy virtual machines (VMs) or complicated dual-boot setups.
First introduced with Windows 10 and later incorporated into Windows Server 2016 and Windows Server 2019, WSL has become an essential utility for IT professionals, developers, network engineers, DevOps teams, and anyone who needs to manage or test applications in a hybrid infrastructure setup. In environments where Windows Server dominates backend systems but Linux powers applications, tools, or test environments, WSL provides the missing link to operate both worlds efficiently from a single machine.
A True Hybrid: Linux on Windows Without the Overhead
Traditionally, if you wanted to run Linux commands on a Windows Server, you had only a few options:
- Set up a full Linux virtual machine using Hyper-V or VMware.
- Configure dual-boot partitions, switching between operating systems.
- Use limited tools like Cygwin or rely on telnetting into a remote Linux box.
Each of these options came with trade-offs whether in performance, complexity, or security. Enter WSL. With just a few PowerShell commands, you can enable WSL and access a fully functional Linux shell, such as Bash, within your Windows Server installation. This means:
- No virtualization overhead
- No rebooting into another OS
- No isolated systems—WSL can access the same file system and network as Windows
This lightweight Linux environment runs as a subsystem, rather than a VM, meaning it’s faster and consumes significantly fewer system resources while still providing the full power of the Linux command line.
Why Use WSL on Windows Server?
Integrating Linux tools into a Windows Server workflow may have once seemed counterintuitive, especially in organizations traditionally rooted in the Microsoft ecosystem. However, in today’s evolving IT environments where agility, flexibility, and cross-platform compatibility are critical, the ability to seamlessly run Linux on Windows Server via Windows Subsystem for Linux (WSL) is no longer a novelty, it’s a necessity.
From developers and DevOps teams to system administrators and cybersecurity professionals, WSL provides a unified space where Linux meets Windows in the most efficient way possible. Let’s explore the top reasons why adopting WSL on Windows Server 2019 can significantly boost productivity, reduce infrastructure complexity, and enhance hybrid operations.
1. Quick and Simple Setup
One of the primary reasons to use WSL on Windows Server is its incredibly straightforward installation process. Unlike traditional solutions that require setting up a full-blown Linux virtual machine, WSL can be enabled with a single PowerShell command. There’s no need to configure virtual CPUs, assign RAM, or manage virtual disks.
Once enabled, you can quickly install a Linux distribution like Ubuntu, Debian, or openSUSE with just a few commands or downloads. This lightweight footprint means WSL can run on almost any Windows Server 2019 machine without needing a dedicated hypervisor or virtual machine manager.
This simplicity is especially valuable in scenarios where time is of the essence. Need to test a Bash script, install a Linux-based tool, or SSH into a device? You can have WSL up and running in under five minutes, compared to the time-intensive process of setting up a VM or dual-boot system.
➡️ Real-world benefit: Imagine troubleshooting a Linux-based web server remotely from your Windows Server. WSL gives you instant access to diagnostic tools without switching environments or incurring additional setup time.
2. Massive Software Repository
Another standout advantage of WSL is access to Linux’s massive open-source software ecosystem. Distributions like Ubuntu come with built-in package managers (e.g., apt, yum, dnf) that allow you to install thousands of software packages directly from the command line. This makes it easy to:
- Install development frameworks like Node.js, Python, Go
- Use cybersecurity tools like nmap, tcpdump, or Wireshark
- Deploy and configure web servers such as Nginx or Apache
- Access cloud tools like AWS CLI, Azure CLI, and Terraform
This level of access and versatility is especially useful for developers who prefer Linux-based libraries or build environments but work within a Windows-managed infrastructure. With WSL, they no longer need to set up a second machine or maintain a separate Linux server for development and testing.
➡️ For system admins, having native access to tools like rsync, cron, and curl via WSL simplifies administrative scripts and task automation across environments without installing third-party Windows equivalents.
3. Familiar Tools and Automation
Linux has long been the preferred platform for scripting and automation. Tools like:
- ssh for secure remote access
- vi or nano for quick file editing
- cron for scheduled tasks
- top and htop for real-time system monitoring
are essential parts of a Linux sysadmin’s toolkit. The ability to access and use these tools natively on Windows Server 2019 is one of WSL’s most powerful features.
WSL empowers Windows-based administrators to:
- Write and run Bash scripts for cross-platform automation
- Manage cron jobs to execute tasks at defined intervals
- Create monitoring scripts that integrate Linux and Server systems
- Use command-line tools to interact with devices across hybrid networks
Additionally, PowerShell and Bash can now coexist. You can run a PowerShell script to perform Windows tasks, and seamlessly call a Bash script within the same workflow for Linux-based operations without leaving your terminal.
➡️ Hybrid scripting scenarios, where part of your infrastructure is on Linux and the rest on Windows, become far more manageable and coherent when both toolsets are available on the same machine.
4. Secure and Updatable
Security is a top priority in modern IT infrastructure, and WSL doesn’t fall short in this domain. Linux distributions running inside WSL support regular updates via their native package managers (apt upgrade, yum update, etc.), ensuring that tools and system components are patched and secure.
What makes this more compelling is the shared update responsibility. You don’t need a separate update schedule for WSL when your Windows Server is patched, you can quickly log into your WSL environment and update Linux components too. This streamlines compliance and reduces the likelihood of unpatched vulnerabilities hiding in separate machines or virtualized environments.
In addition to software updates, WSL runs in a user-mode container and does not allow for direct kernel access or elevated root-level modifications to your Windows OS, making it inherently more secure than a traditional Linux VM.
➡️ For security-conscious environments, WSL is a trustworthy way to run Linux tools without introducing major attack vectors or system instability.
5. Boosts Interoperability Between Linux and Windows
One of WSL’s greatest strengths is how it fosters interoperability between Linux and Windows Server. The file systems are integrated, meaning you can access your C: drive from Linux (/mnt/c/) and even run scripts that interact across the platforms.
You can:
- Edit Windows files using Linux tools like sed and awk
- Move files between environments effortlessly
- Share logs, configs, and outputs between Bash and PowerShell
WSL supports cross-platform workflows like few other tools, allowing DevOps engineers, developers, and sysadmins to merge the best of both ecosystems.
➡️ For example, you can build a website in a Linux-based Node.js environment, test it, and then deploy it using a PowerShell deployment script to your IIS server—all on the same Windows Server box.
How to Install WSL on Windows Server 2019 Using PowerShell
Installing WSL on Windows Server 2019 can be done in just a few steps:
Step 1: Enable WSL
Open PowerShell as Administrator and run the following command:
powershell
CopyEdit
Enable-WindowsOptionalFeature -Online -FeatureName Microsoft-Windows-Subsystem-Linux
Your server will need to restart after this step. Be sure to save your work beforehand.
Step 2: Download Your Preferred Linux Distribution
For example, to install Ubuntu 16.04:
powershell
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Invoke-WebRequest -Uri https://aka.ms/wsl-ubuntu-1604 -OutFile Ubuntu.appx -UseBasicParsing
Place the downloaded .appx file in a directory like C:\Windows\System32.
Step 3: Extract and Set Up
Convert the .appx file into a ZIP archive and extract the contents using any tool like 7-Zip or the Expand-Archive PowerShell cmdlet.
Step 4: Register the Distro
To complete the setup, execute the Linux binary:
powershell
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C:\Windows\System32\Ubuntu\ubuntu1604.exe
This initializes the Linux shell environment.
Step 5: Launch WSL
Open Command Prompt or PowerShell with admin rights and simply type:
bash
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wsl
You’re now logged into your Linux environment inside Windows Server 2019.
Real-World Use Cases for WSL on Windows Server
With Windows Subsystem for Linux (WSL), Microsoft has given system administrators, developers, and IT professionals a powerful tool to seamlessly integrate Linux functionality within Windows Server environments. Beyond convenience, WSL unlocks entirely new possibilities for managing infrastructure, deploying software, automating tasks, and improving efficiency in hybrid ecosystems.
Let’s break down some compelling real-world scenarios where WSL on Windows Server 2019 proves invaluable.
Scenario 1: Accessing Linux Apps on Demand
Need to log into a Cisco router using SSH, or troubleshoot a Linux configuration file using vi or nano? With WSL installed on your Windows Server, these classic Linux tools are just a command away.
In mixed-environment organizations, where Windows manages core infrastructure and Linux handles applications or network appliances, system administrators often bounce between platforms. Normally, this would require remote SSH access into Linux boxes or launching a full Linux VM. WSL eliminates that need.
Using tools like:
- ssh: to securely log into network devices or Linux servers
- scp: for secure file transfers
- rsync: to mirror directories efficiently
- nmap: for port scanning and network auditing
…you can perform mission-critical tasks from a single Windows Server machine.
💡 Example Use Case: You’re managing a server rack where the firewalls and switches use Linux-based interfaces. Instead of logging into each appliance from a separate terminal, you open your WSL shell in Windows Server and run ssh [email protected] to immediately manage your device. Then you use scp to back up configuration files or push firmware updates.
Having Linux-native tools within your Windows Server workflow means fewer interruptions, reduced software dependencies, and a more agile IT response.
Scenario 2: Development and Testing
Developers working in Python, Node.js, Ruby, Go, or Bash scripting benefit immensely from having access to a true Linux environment on Windows. With WSL, you can:
- Clone Git repositories
- Build and test code in a Linux runtime
- Access command-line compilers and interpreters
- Manage project dependencies using native package managers (e.g., pip, npm, go get)
All of this happens without needing to deploy a full Linux VM, which saves resources and simplifies the developer experience.
💡 Integration with Visual Studio Code: The VS Code Remote WSL extension lets you use your familiar GUI interface while editing files and running terminals directly inside your WSL environment. This is incredibly helpful for debugging and refactoring, allowing developers to enjoy the best of both Windows and Linux from a single workstation or server.
Upgrading to WSL 2 for Deeper Compatibility
While WSL 1 is fast and sufficient for many scripting and CLI-based tasks, developers who require system call compatibility, Docker support, or deep file system integration should consider WSL 2.
Benefits of WSL 2 include:
- A real Linux kernel, improving compatibility
- Support for Docker and Kubernetes tools
- Faster file system performance with native ext4 support
- Enhanced memory management
💡 Dev/Test Environment Example: Suppose you’re testing a Python web app that depends on Ubuntu-specific packages. You can build, test, and run your application entirely in WSL—then later deploy to a Linux production server with confidence, knowing the environments match.
Scenario 3: Cross-Platform Administration
In many organizations, it’s not uncommon to have Windows-based domain controllers, Active Directory servers, and SQL databases running alongside Linux-based web servers, proxy systems, or DNS tools. This mixture often complicates day-to-day operations for sysadmins.
Enter WSL: it converts your Windows Server 2019 box into a multi-platform control hub.
Here’s what cross-platform administration looks like with WSL:
- Use PowerShell to manage Active Directory and Windows services.
- Use Bash inside WSL to manage Linux servers via SSH.
- Execute scheduled scripts across environments.
- Analyze both Linux and Windows logs from a single interface.
- Mount and manage network shares from either OS flavor.
💡 Real-world Example: An admin needs to sync web server logs from a Linux host to a Windows Server for centralized monitoring. Using rsync from within WSL, the logs are pulled directly into the Windows Server without needing additional third-party software or external devices.
This integration allows you to:
- Reduce the number of devices needed to manage infrastructure.
- Eliminate context switching and redundant remote sessions.
- Accelerate diagnostics and configuration in real time.
For IT teams tasked with maintaining diverse infrastructures, WSL is a game-changing tool that breaks down silos between systems.
Scenario 4 (Bonus): Security and Resource Efficiency
WSL not only streamlines administration and development—it does so securely and efficiently.
Unlike full-blown virtual machines, which require a hypervisor (like Hyper-V or VMware), WSL operates in a low-overhead environment. This brings several advantages:
✅ Lower Resource Usage
- No need to allocate separate RAM or CPUs
- WSL instances share host resources dynamically
- Perfect for servers with limited headroom
✅ Faster Boot Times
- WSL starts in under a second
- Scripts and apps run instantly
- No need to “power on” a virtual machine
✅ Secure Execution Model
- WSL runs in user space, with limited access to kernel-level resources
- Linux distros in WSL cannot affect the Windows kernel
- Updates are handled via native tools like apt or yum, meaning WSL can be patched and maintained independently
💡 Security Benefit: Since WSL can’t modify the underlying Windows OS directly, it provides a safe space to test potentially risky commands, inspect third-party scripts, or even simulate attacks in a controlled setting—all without compromising system stability.
For teams with tight security protocols, WSL offers a balance of Linux power and Windows protection.
Wrapping Up: WSL as a Productivity Multiplier in Hybrid Environments
These real-world use cases make it clear that WSL on Windows Server 2019 is much more than a niche feature it’s a strategic enabler of hybrid computing, DevOps workflows, and modern administration.
Whether you’re managing routers, writing backend APIs, deploying to Kubernetes clusters, or scripting server diagnostics, WSL gives you the Linux tools you need – right where you are.
By combining the strength of the Windows ecosystem with the versatility of Linux tools, WSL unlocks new opportunities for businesses, teams, and individuals navigating an increasingly cross-platform digital landscape.
PowerShell + Bash = Better Together
In the world of IT operations, there has historically been a dividing line between administrators who specialize in Windows and those who prefer Linux. Each platform has its own scripting language, ecosystem, and best practices PowerShell for Windows and Bash for Linux. However, with the introduction of Windows Subsystem for Linux (WSL) and broader support for open-source development tools within Microsoft’s environment, these lines are increasingly blurring.
There’s a common misconception that embracing Bash somehow diminishes the role or importance of PowerShell in a Windows Server environment. In reality, nothing could be further from the truth. The two tools are complementary, not competitive. Together, they form a hybrid powerhouse for managing today’s complex, mixed-platform infrastructures.
Let’s explore how PowerShell and Bash can work in harmony to deliver flexible, efficient, and robust solutions across development, automation, and system administration.
PowerShell: The Champion of Windows Internals
PowerShell was designed specifically to interact with the inner workings of the Windows operating system. It’s object-oriented, supports .NET libraries, and allows administrators to manage:
- Active Directory (AD): user/group creation, OU management, domain policies
- Group Policy: view and modify GPOs programmatically
- Windows Services: start/stop services, check event logs
- File Systems: copy, move, delete files with advanced logic
- Server Roles: automate IIS, DNS, DHCP configurations
For Windows sysadmins, PowerShell is indispensable. It makes tasks that were previously only GUI-accessible (or scriptable via legacy batch files) now scriptable, repeatable, and scalable.
Bash: The Automation and Text-Processing Wizard
While PowerShell shines within the Windows realm, Bash brings the raw efficiency of the Linux command-line ecosystem. It thrives in text manipulation, scripting pipelines, and network administration.
Some strengths of Bash include:
- Fast, scriptable access to thousands of tools (awk, sed, grep, etc.)
- Easy file parsing and pattern recognition
- Simplified cron-based scheduling
- Efficient SSH-based remote administration
- Lightweight scripts for automating Linux services
The Best of Both Worlds: Why Use Them Together?
Thanks to WSL, you can now run Bash scripts directly on Windows Server 2019 alongside PowerShell. This means:
- Windows-native tasks can be scripted with PowerShell.
- Linux-based operations can be executed in Bash.
- Both can share access to files, network resources, and environment variables.
You’re no longer forced to pick one or the other. Instead, you can combine the strengths of both tools into a cohesive workflow.
🔄 Real-World Integration: Mixed-Script Automation
Let’s say you’re deploying a new app across an environment that includes:
- Windows-based web servers (IIS)
- Linux-based database servers (MySQL on Ubuntu)
- DNS updates for internal name resolution
Your deployment script could look like this:
- Use PowerShell to create and configure new IIS sites.
- Switch to Bash to automate MySQL provisioning.
- Return to PowerShell to update DNS entries using dnscmd.
Or even better combine both in a single workflow: Security and Permissions Management
In environments where role-based access control and least-privilege policies are critical, PowerShell and Bash serve different but necessary roles.
- Use PowerShell to audit and enforce Active Directory policies.
- Use Bash to check /etc/passwd and file permissions on Linux nodes.
Running both environments within WSL on Windows Server means that system administrators can enforce policies and audit controls from a centralized location, without relying on third-party management consoles.
DevOps and CI/CD Pipelines
Many modern DevOps workflows leverage tools like:
- Jenkins
- Azure DevOps
- GitHub Actions
- Docker and Kubernetes
These tools often require both Windows- and Linux-compatible scripts. WSL allows build agents running on Windows Server to execute Bash-based steps natively eliminating the need for Linux runners or additional VMs.
Example: Suppose your pipeline includes these stages:
- Build .NET Core app (PowerShell)
- Run unit tests (PowerShell)
- Compile frontend with npm (Bash)
- Deploy via SSH to a Linux host (Bash)
WSL makes this possible, all within one build node.
Team Collaboration and Skill Bridging
Another overlooked advantage of blending PowerShell and Bash is that it fosters cross-skill collaboration. Admins who’ve spent their careers in one ecosystem can learn the other gradually, without jumping to another OS.
- Windows admins can try Bash without leaving their comfort zone.
- Linux admins can begin exploring PowerShell cmdlets for Windows automation.
This leads to stronger, more versatile IT teams, especially in organizations undergoing cloud transformation or working within hybrid server environments.
Final Thoughts: Synergy Over Segregation
In the past, Windows and Linux teams often operated in silos, relying on completely different tools, workflows, and machines. But with the rise of cloud-native, DevOps, and platform-agnostic technologies, those walls are falling.
PowerShell and Bash are not rivals they’re allies.
Together, they create a robust scripting and automation environment for:
- Full-stack system administration
- Cross-platform DevOps pipelines
- Secure and efficient IT operations
- Learning and experimentation
- Hybrid cloud infrastructure management
Thanks to WSL in Windows Server 2019, you can run both environments side by side, no VMs, no dual booting, no limitations. Whether you’re managing AD users, configuring Linux daemons, processing logs, or pushing production builds, combining PowerShell and Bash means you’re working smarter, not harder.
