SSH Access to Windows Server: A Guide

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LokerSSH.com – SSH (Secure Shell) is one of the most reliable and secure ways to remotely access and manage a server. Although SSH is commonly used with Linux-based systems, Windows Server can also be configured to support SSH connections. With SSH enabled on your Windows Server, administrators and developers can securely execute commands, perform system configurations, and transfer files remotely, much like they would on a Linux machine.

In this comprehensive guide, we’ll walk you through how to set up and use SSH access to Windows Server to enhance remote management and improve your workflow.

Why Use SSH Access to Windows Server?

1. Secure Remote Access

Unlike older remote management protocols like RDP or Telnet, SSH encrypts data during transmission, providing enhanced security when managing servers. With SSH access to Windows Server, you can connect remotely without exposing sensitive information to potential eavesdropping.

2. Streamlined Command-Line Management

SSH allows system administrators to access the Windows Command Prompt or PowerShell directly, enabling them to run commands, scripts, or even troubleshoot without the need for a graphical user interface (GUI). This is particularly useful for managing servers remotely or automating repetitive tasks.

3. Improved Efficiency

By enabling SSH on your Windows Server, you can perform management tasks more quickly and efficiently, whether you’re updating software, managing system configurations, or performing diagnostics. The ability to use PowerShell or Command Prompt remotely via SSH adds flexibility to your workflow.

Prerequisites for Enabling SSH Access on Windows Server

Before you proceed, make sure your system meets the following requirements:

  1. Windows Server Version: SSH is supported on Windows Server 2019 and later. For earlier versions, you may need to consider alternative methods or upgrade.
  2. Administrator Privileges: You need administrator access to install and configure SSH on your Windows Server.
  3. Windows Features: Make sure that OpenSSH Server is available and ready to be installed on your system.

Step-by-Step Guide: Enabling SSH Access to Windows Server

Step 1: Install OpenSSH Server on Windows Server

Windows Server 2019 and later include OpenSSH as an optional feature. Here’s how to install the OpenSSH Server on Windows Server:

1.1 Open PowerShell as Administrator

  • Click the Start Menu, type PowerShell, and right-click to choose Run as Administrator.

1.2 Install OpenSSH Server Feature

To install the OpenSSH Server feature, run the following PowerShell command:

Add-WindowsFeature -Name OpenSSH-Server

Alternatively, you can install OpenSSH Server through Windows Settings by navigating to Settings > Apps > Optional Features > Add a Feature and selecting OpenSSH Server from the list.

1.3 Verify Installation

To confirm that OpenSSH Server is installed, run:

Get-WindowsFeature -Name OpenSSH-Server

If installed successfully, it should show as Installed.

Step 2: Start the OpenSSH Server

Once the OpenSSH Server is installed, you need to start it to allow SSH access.

2.1 Start the SSH Service

Run the following command in PowerShell to start the OpenSSH server:

Start-Service sshd

2.2 Enable SSH Server to Start Automatically

To ensure that the SSH service starts automatically whenever the Windows Server reboots, run this command:

Set-Service -Name sshd -StartupType 'Automatic'

Step 3: Allow SSH Through the Windows Firewall

By default, Windows Firewall may block incoming SSH connections. You need to create a rule that allows SSH traffic to reach your server.

3.1 Create a Firewall Rule for SSH

To allow SSH through the firewall, run the following PowerShell command:

New-NetFirewallRule -Name sshd -DisplayName 'OpenSSH Server (sshd)' -Enabled True -Protocol TCP -Action Allow -LocalPort 22

This command opens port 22, which is the default port used for SSH connections.

Step 4: Test SSH Access to Your Windows Server

4.1 Check SSH Service Status

To ensure that the SSH service is running, you can check its status using:

Get-Service sshd

If the sshd service is running, it should display Running as its status.

4.2 Test the SSH Connection

You can now test the SSH connection from another machine. Use an SSH client (e.g., PuTTY or OpenSSH in Linux/macOS) and connect to the Windows Server by typing:

ssh username@your-server-ip

Replace username with your Windows server login name and your-server-ip with the server’s IP address.

If everything is configured correctly, you will be prompted for your password and then granted remote access to the Windows Server.

Step 5: Optional Configuration – Enable SSH Key Authentication

For better security, you can set up SSH key-based authentication. This method eliminates the need for a password, replacing it with a more secure, cryptographic key pair.

5.1 Generate SSH Key Pair

Generate an SSH key pair on the local machine you will be using to connect to the Windows Server. On Linux/macOS, you can generate the key pair by running:

ssh-keygen

On Windows, you can use PuTTYgen to create the key pair.

5.2 Copy the Public Key to the Windows Server

Copy the public key to the C:\Users\<username>\.ssh\authorized_keys file on your Windows Server. If the .ssh folder doesn’t exist, you can create it manually.

5.3 Modify SSH Configuration for Key Authentication

Edit the sshd_config file located at:

C:\ProgramData\ssh\sshd_config

Ensure the following lines are included:

PubkeyAuthentication yes
AuthorizedKeysFile      .ssh/authorized_keys

5.4 Restart the SSH Service

After modifying the configuration, restart the SSH service:

Restart-Service sshd

5.5 Test SSH Key Authentication

To test key-based authentication, use the following command (substituting in the correct path to your private key):

ssh -i /path/to/private_key username@your-server-ip

Troubleshooting SSH Access to Windows Server

  • SSH Service Not Running: If the SSH service is not running, check the service status with Get-Service sshd. Start the service manually using Start-Service sshd.
  • Firewall Issues: Ensure that port 22 is open in Windows Firewall. Use the New-NetFirewallRule command to create the appropriate rule.
  • Permission Problems: Make sure that the .ssh directory and the authorized_keys file have proper permissions. The .ssh directory should have 700 permissions, and the authorized_keys file should have 600 permissions.

Conclusion

Enabling SSH access to Windows Server provides a secure, efficient, and flexible way to manage your server remotely. By following this guide, you’ll be able to install and configure OpenSSH on your Windows Server, enable secure SSH access, and even set up SSH key-based authentication for a more seamless and secure remote management experience.

Whether you’re managing a single server or multiple machines, SSH on Windows Server is an essential tool for system administrators looking to streamline their workflow and enhance security.

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