SSH tips on Windows

• Mar 31, 2024
• •
• 3 min read
• •
• Snippets •
• DevOps

Windows 11 includes an OpenSSH client b default. You can use it directly from the PowerShell or command prompt terminal.

Connecting to a Linux server #

Open a terminal and run the following command:

ssh [email protected]

Replace username with your Linux server username and 12.34.56.78 with the server’s IP address. The first time you connect, you’ll be prompted to accept the host key. After that, enter your password to log in. To log out, run the exit command or press Ctrl+D.

If your Linux server has a different SSH port, let's say 10322, use the -p flag:

ssh [email protected] -p 10322

Downloading/uploading files between your Windows client and a Linux server #

Use WinSCP for that.

Tools #

• PuTTY
• WinSCP
• PuTTYgen

Additional Resources #

• https://learn.microsoft.com/en-us/windows-server/administration/openssh/openssh_install_firstuse?tabs=gui
• https://docs.bitnami.com/aws/faq/get-started/access-ssh-tunnel/
• https://docs.vultr.com/port-forwarding-and-proxying-using-openssh

Managing SSH Keys with OpenSSH and Bitwarden #

1. Set up your environment #

Create the SSH directory if it doesn't exist:

mkdir -p $env:USERPROFILE\.ssh

2. Generate SSH Key Pair #

1. Open PowerShell and generate an Ed25519 key (recommended):

ssh-keygen -t ed25519 -C "[email protected]"

Or RSA if required:

ssh-keygen -t rsa -b 4096 -C "[email protected]"

2. When prompted:
   • Save to default location (%USERPROFILE%\.ssh\id_ed25519 or id_rsa)
   • Set a strong passphrase

This creates two files:

• Private key: id_ed25519 (no extension)
• Public key: id_ed25519.pub

3. Store in Bitwarden #

1. Open Bitwarden and create a new Secure Note
2. Title: "SSH Key - [Purpose]" (e.g., "SSH Key - Work Laptop 2024")
3. Add attachments:
   • Browse to %USERPROFILE%\.ssh\
   • Attach both id_ed25519 and id_ed25519.pub
4. Add to notes:

Server: example.com
Username: myuser
Key Type: Ed25519
Created: [Date]
Passphrase: [your-passphrase]

Public Key:
[paste contents of id_ed25519.pub here]

Usage:
1. Download private key
2. Save to ~/.ssh/id_ed25519
3. Set permissions: chmod 600 ~/.ssh/id_ed25519

5. Add tags: "ssh", "credentials", "work"
6. Save

4. Deploy to Server #

1. Copy your public key to the server:

# Method 1: Using ssh-copy-id (if available)
ssh-copy-id -i ~/.ssh/id_ed25519.pub username@example.com

# Method 2: Manual copy
type $env:USERPROFILE\.ssh\id_ed25519.pub | ssh username@example.com "mkdir -p ~/.ssh && cat >> ~/.ssh/authorized_keys"

2. Verify the connection:

ssh -i $env:USERPROFILE\.ssh\id_ed25519 username@example.com

5. Recovery Process #

If you need to recover access from a new device:

1. Install OpenSSH client if not present:

Add-WindowsCapability -Online -Name OpenSSH.Client~~~~0.0.1.0

2. Create SSH directory:

mkdir -p $env:USERPROFILE\.ssh

3. Download private key from Bitwarden
4. Save as %USERPROFILE%\.ssh\id_ed25519
5. Set correct permissions:

icacls "%USERPROFILE%\.ssh\id_ed25519" /inheritance:r /grant:r "%USERNAME%":"F"

6. Test connection:

ssh -i $env:USERPROFILE\.ssh\id_ed25519 username@example.com

7. After recovery, generate new keys and update servers

Connecting to Servers with SSH Keys #

1. Basic connection with default key location:

ssh username@192.168.1.100

2. Specify a different port (e.g., 10322):

ssh -p 10322 username@192.168.1.100

3. Explicitly specify which key to use:

ssh -i $env:USERPROFILE\.ssh\id_ed25519 username@192.168.1.100

4. For multiple servers/keys, create a config file at %USERPROFILE%\.ssh\config:

Host myserver1
    HostName 192.168.1.100
    User username
    Port 22
    IdentityFile ~/.ssh/id_ed25519

Host myserver2
    HostName 192.168.1.200
    User otheruser
    Port 10322
    IdentityFile ~/.ssh/id_rsa

Then connect using the alias:

ssh myserver1

💡 Tip: After adding your key to a server, you won't need to enter a password. You'll only need the key's passphrase (if you set one).

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