For years, deploying code to Windows servers meant one set of tools, while Linux deployments required another. Different protocols, different workflows, different headaches.
That's changed.
OpenSSH—the secure remote access standard that's been the backbone of Linux server management for decades—is now fully integrated into Windows. This isn't just a technical update. It's a fundamental shift that lets you manage all your servers, regardless of operating system, with the same secure, automatable toolset.
If you're running mixed environments, or even if you're purely Windows-based but tired of clunky deployment processes, this matters. A lot.
This post will show you what OpenSSH is, why Microsoft's adoption of it is a game-changer, and how it can transform your deployment pipelines from fragmented and manual to unified and automated. At DeployHQ, we've built our platform around these principles, and we're excited to show you what's possible.
What Exactly is OpenSSH? Your Secure Gateway to Remote Servers
OpenSSH (Open Secure Shell) is a suite of open-source tools that creates encrypted connections between computers. Think of it as a fortified tunnel through the internet: everything that passes through—passwords, commands, file transfers—is protected from prying eyes.
Developed as part of the security-focused OpenBSD project, OpenSSH has become the de facto standard for secure server access. Here's what makes it powerful:
The Core Tools You'll Use
Secure Shell (ssh) - The heart of the suite. This lets you log into a remote server and run commands as if you were sitting at the keyboard. Every keystroke and response is encrypted.
Secure File Transfer (sftp) - Upload your application code, configuration files, and assets to servers securely. This has largely replaced the older, insecure FTP protocol. For deployments, this is how your code gets from your repository to your production server.
Secure Copy (scp) - Quick, scriptable file transfers between servers. Perfect for automated deployment scripts that need to move files without interaction.
Other Useful Features
Beyond these core tools, OpenSSH includes SSH tunneling (port forwarding) for securely accessing database admin panels or other internal services, and SSHFS for mounting remote directories as if they were local drives. The OpenSSH project page details all capabilities.
Security That Actually Works
OpenSSH's strength comes from two key mechanisms:
Encryption - Military-grade cryptographic algorithms protect all data in transit.
Key-based authentication - Instead of passwords (which can be guessed or stolen), you generate a cryptographic key pair. Your private key stays on your machine, your public key goes on the server. The server verifies your identity mathematically, making brute-force attacks essentially impossible.
This is why security-conscious organizations and frameworks like NIST recommend SSH for all remote system administration.
Why OpenSSH Matters: Security, Automation, Standardization
OpenSSH's rise to universal adoption isn't accidental. It excels in three areas that define modern infrastructure management:
Security First
In an era of sophisticated cyber threats, encrypted communication is non-negotiable. OpenSSH is developed by the security-focused OpenBSD project, and because it's open source, thousands of security researchers worldwide scrutinize its code. Vulnerabilities are identified and patched rapidly.
The NIST (National Institute of Standards and Technology) regularly references SSH in security guidelines for system administration. When government security agencies trust a protocol, you know it's solid.
Built for Automation
OpenSSH is command-line native, making it inherently scriptable. This is critical for DevOps practices where manual server management doesn't scale.
Tools like Ansible, Chef, Puppet, and DeployHQ rely heavily on SSH to securely connect to servers and execute automated workflows. Whether you're provisioning new infrastructure, deploying code, or running configuration updates, SSH is the secure transport layer that makes automation possible.
Without OpenSSH, the modern DevOps landscape would be far more complex and fragmented.
Cross-Platform Standardization
OpenSSH is available by default on virtually every Linux and macOS system, and now it's fully supported on Windows. This means developers, system administrators, and automated tools can use a consistent approach across all platforms.
One set of deployment scripts. One security model. One learning curve.
The Internet Engineering Task Force (IETF) maintains the SSH protocol specification (RFC 4251), cementing its role as an industry standard.
OpenSSH on Windows: Breaking Down the Walls
For years, Windows remote administration centered on Remote Desktop Protocol (RDP). While RDP provides a full graphical interface (useful for certain tasks), it doesn't lend itself to the automation and scripting that OpenSSH enables. Managing mixed Windows and Linux environments meant juggling completely different toolsets.
Microsoft's decision to fully integrate OpenSSH into Windows—starting with Windows 10 and Windows Server 2019 around 2018—was a watershed moment. You can see Microsoft's official documentation on OpenSSH in Windows for implementation details.
This native support means:
You can install an OpenSSH client to connect from Windows to any SSH server.
You can install an OpenSSH server on Windows, allowing other machines and automated tools to connect to it securely using SSH.
This unlocks:
Consistent scripting - PowerShell scripts can be executed remotely via SSH, just like Bash scripts on Linux.
Unified tooling - Configuration management and deployment platforms can use SSH as a universal transport for both Windows and Linux.
Simplified workflows - Teams can use the same SSH-based techniques regardless of target OS.
This isn't about replacing RDP, which still has its place for GUI-intensive tasks. It's about offering a powerful, secure, automation-friendly alternative that aligns Windows server management with modern DevOps practices.
See It in Action: Linux vs. Windows Commands
One of the beauties of OpenSSH on Windows is that the connection method is identical—only the commands you run differ. Here's what a deployment step looks like:
Connecting to a Linux server:
# Connect and restart the application service
ssh user@linux-server 'systemctl restart myapp'
# Upload files via SFTP
sftp user@linux-server << EOF
put -r ./build/* /var/www/myapp/
EOF
Connecting to a Windows server:
# Connect and restart the application service
ssh user@windows-server 'Restart-Service -Name "myapp"'
# Upload files via SFTP (identical syntax!)
sftp user@windows-server << EOF
put -r ./build/* C:/inetpub/myapp/
EOF
Notice what's the same: The SSH connection, the SFTP syntax, the security model.
What's different: Only the specific commands (systemctl vs. Restart-Service) and file paths. This is the unified workflow that was impossible before Windows adopted OpenSSH.
The Tangible Benefits for Your Deployments
When you apply OpenSSH to your deployment pipeline, the advantages become immediately clear.
Consider a typical deployment: transfer application files, run pre-deployment scripts (database migrations, dependency installations), execute the deployment, run post-deployment scripts (restart services, clear caches).
OpenSSH, through SFTP/SCP and remote command execution, provides a secure and automatable way to handle all of these steps:
Enhanced security for file transfers - SFTP encrypts your entire deployment session. Unlike older protocols like FTP, credentials and code are protected end-to-end.
Reliable automation - SSH's command-line design makes scripting trivial. Deployments become repeatable and consistent, eliminating manual errors.
Unified deployment logic - Write deployment scripts that use SSH, and they work similarly whether targeting Linux or Windows (with appropriate command adjustments). The secure remote execution mechanism is identical.
Consistent configuration management - Tools that enforce server configurations via SSH can now extend seamlessly to Windows servers, ensuring your entire infrastructure is configured uniformly.
OpenSSH + DeployHQ: Your Deployment Pipeline, Simplified
Here's the promise: Push your code. Watch it deploy securely to all your servers—Linux, Windows, or both—without manual intervention. No separate tools. No context switching.
DeployHQ makes this real by leveraging OpenSSH as the foundation for all server connections. Whether you're deploying to a single Windows server or orchestrating updates across a dozen mixed-OS machines, the process is identical.
How It Works
1. Secure Connections by Default
Connect your servers to DeployHQ using SFTP over SSH. We strongly recommend SSH key authentication (we'll walk you through setup), which is far more secure than passwords. Add your server once, and DeployHQ handles all future connections automatically.
2. Run Commands at Every Stage
Need to stop a service before deployment? Run database migrations? Clear a cache afterward? DeployHQ lets you execute commands at precise points in your deployment:
- Before file transfer
- After transfer (but before switching to the new version)
- After deployment completes
On Windows servers with OpenSSH, these can be PowerShell commands. On Linux, Bash scripts. Same pipeline, different commands—DeployHQ handles both seamlessly.
3. Zero-Downtime Deployments
Our atomic deployment feature works by uploading new code to a separate directory, then instantly switching a symlink when everything's ready. If something goes wrong, rolling back is just another symlink swap. This works identically on Windows and Linux servers running OpenSSH, minimizing downtime and risk.
4. Build and Deploy in One Flow
If you're using our build pipelines to compile assets or run tests, the built artifacts deploy to your Windows servers via SFTP/SSH just as easily as to any Linux target. One build, many destinations.
The Real-World Impact
By configuring your Windows servers to use OpenSSH, you unlock the same robust deployment capabilities in DeployHQ that Linux users have enjoyed for years. Your Windows deployment targets become first-class citizens with:
- The same security model
- The same automation capabilities
- The same deployment workflows
- The same ease of configuration
This unification simplifies your DeployHQ setup, makes your pipelines more consistent, and reduces the operational overhead of managing diverse environments.
Building a Unified and Secure Future
OpenSSH's evolution from a Unix utility to a universal standard for secure remote operations demonstrates the power of open-source development and industry collaboration. Its integration into Windows is more than a technical milestone—it's a paradigm shift toward unified, secure, and automated infrastructure management.
At DeployHQ, we've embraced this shift wholeheartedly. By using OpenSSH for connections to all your servers, we provide a deployment experience that's simpler, safer, and more powerful.
Ready to Get Started?
Whether you're managing mixed environments, transitioning to Windows-based deployments, or simply looking to modernize your deployment pipeline, OpenSSH provides the foundation you need.
Here's how to begin:
- Install OpenSSH on your Windows servers - Follow Microsoft's official guide
- Set up SSH key authentication - More secure than passwords and required for true automation
- Connect your servers to DeployHQ - Configure SFTP/SSH connections in minutes
- Deploy your first cross-platform pipeline - Watch code flow seamlessly to all your infrastructure
The future of deployment is unified, secure, and automated. OpenSSH is your bridge to that future.
Ready to simplify your deployments? Start your free DeployHQ trial today and experience the power of unified, SSH-based deployments across all your servers.