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Several tools exist to generate SSH public/private key pairs. The following sections show how to generate an SSH key pair on UNIX, UNIX-like and Windows platforms.

To generate the public/private key pair, enter this in the Command Prompt: ssh-keygen At the first prompt, “Enter file in which to save the key,” press Enter to save it in the default location.

Generating an SSH Key Pair on UNIX and UNIX-Like Platforms Using the ssh-keygen Utility

• Installing the public key as an authorized key on a server. With both Tectia SSH and OpenSSH servers, access to an account is granted by adding the public key to a /.ssh/authorizedkeys file on the server. To install the public key, Log into the server, edit the authorizedkeys file with your favorite editor, and cut-and-paste the public key output by the above command to the authorizedkeys file. Save the file.
• Upload public key to Bitvise SSH Server. Before you can use public key authentication, the public key for the keypair you have generated must be configured in the SSH Server. If you are able to connect to the SSH Server using password authentication, you can connect to the server and upload the public key using the Client key manager.

UNIX and UNIX-like platforms (including Solaris and Linux) include the ssh-keygen utility to generate SSH key pairs.

1. Navigate to your home directory:
2. Run the ssh-keygen utility, providing as filename your choice of file name for the private key:

   The ssh-keygen utility prompts you for a passphrase for the private key.

3. Enter a passphrase for the private key, or press Enter to create a private key without a passphrase:

   Note:

   While a passphrase is not required, you should specify one as a security measure to protect the private key from unauthorized use. When you specify a passphrase, a user must enter the passphrase every time the private key is used.

   The ssh-keygen utility prompts you to enter the passphrase again.

4. Enter the passphrase again, or press Enter again to continue creating a private key without a passphrase:
5. The ssh-keygen utility displays a message indicating that the private key has been saved as filename and the public key has been saved as filename.pub. It also displays information about the key fingerprint and randomart image.

Generating an SSH Key Pair on Windows Using the PuTTYgen Program

The PuTTYgen program is part of PuTTY, an open source networking client for the Windows platform.

1. Download and install PuTTY or PuTTYgen.

   To download PuTTY or PuTTYgen, go to http://www.putty.org/ and click the You can download PuTTY here link.

2. Run the PuTTYgen program.
3. Set the Type of key to generate option to SSH-2 RSA.
4. In the Number of bits in a generated key box, enter 2048.
5. Click Generate to generate a public/private key pair.

   As the key is being generated, move the mouse around the blank area as directed.

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6. (Optional) Enter a passphrase for the private key in the Key passphrase box and reenter it in the Confirm passphrase box.

   Note:

   While a passphrase is not required, you should specify one as a security measure to protect the private key from unauthorized use. When you specify a passphrase, a user must enter the passphrase every time the private key is used.

7. Click Save private key to save the private key to a file. To adhere to file-naming conventions, you should give the private key file an extension of .ppk (PuTTY private key).

   Note:

   The .ppk file extension indicates that the private key is in PuTTY's proprietary format. You must use a key of this format when using PuTTY as your SSH client. It cannot be used with other SSH client tools. Refer to the PuTTY documentation to convert a private key in this format to a different format.
8. Select all of the characters in the Public key for pasting into OpenSSH authorized_keys file box.

   Make sure you select all the characters, not just the ones you can see in the narrow window. If a scroll bar is next to the characters, you aren't seeing all the characters.

9. Right-click somewhere in the selected text and select Copy from the menu.
10. Open a text editor and paste the characters, just as you copied them. Start at the first character in the text editor, and do not insert any line breaks.
11. Save the text file in the same folder where you saved the private key, using the .pub extension to indicate that the file contains a public key.
12. If you or others are going to use an SSH client that requires the OpenSSH format for private keys (such as the ssh utility on Linux), export the private key:
    1. On the Conversions menu, choose Export OpenSSH key.
    2. Save the private key in OpenSSH format in the same folder where you saved the private key in .ppk format, using an extension such as .openssh to indicate the file's content.

Most authentication in Windows environments is done with a username-password pair.This works well for systems that share a common domain.When working across domains, such as between on-premise and cloud-hosted systems, it becomes more difficult.

By comparison, Linux environments commonly use public-key/private-key pairs to drive authentication.OpenSSH includes tools to help support this, specifically:

• ssh-keygen for generating secure keys
• ssh-agent and ssh-add for securely storing private keys
• scp and sftp to securely copy public key files during initial use of a server

This document provides an overview of how to use these tools on Windows to begin using key authentication with SSH.If you are unfamiliar with SSH key management, we strongly recommend you review NIST document IR 7966 titled 'Security of Interactive and Automated Access Management Using Secure Shell (SSH).'

About key pairs

Key pairs refer to the public and private key files that are used by certain authentication protocols.

SSH public-key authentication uses asymmetric cryptographic algorithms to generate two key files – one 'private' and the other 'public'. The private key files are the equivalent of a password, and should protected under all circumstances. If someone acquires your private key, they can log in as you to any SSH server you have access to. The public key is what is placed on the SSH server, and may be shared without compromising the private key.

When using key authentication with an SSH server, the SSH server and client compare the public key for username provided against the private key. If the public key cannot be validated against the client-side private key, authentication fails.

Multi-factor authentication may be implemented with key pairs by requiring that a passphrase be supplied when the key pair is generated (see key generation below).During authentication the user is prompted for the passphrase, which is used along with the presence of the private key on the SSH client to authenticate the user.

Host key generation

Public keys have specific ACL requirements that, on Windows, equate to only allowing access to administrators and System.To make this easier,

• The OpenSSHUtils PowerShell module has been created to set the key ACLs properly, and should be installed on the server
• On first use of sshd, the key pair for the host will be automatically generated. If ssh-agent is running, the keys will be automatically added to the local store.

To make key authentication easy with an SSH server, run the following commands from an elevated PowerShell prompt:

Since there is no user associated with the sshd service, the host keys are stored under ProgramDatassh.

User key generation

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To use key-based authentication, you first need to generate some public/private key pairs for your client.From PowerShell or cmd, use ssh-keygen to generate some key files.

This should display something like the following (where 'username' is replaced by your user name)

You can hit Enter to accept the default, or specify a path where you'd like your keys to be generated.At this point, you'll be prompted to use a passphrase to encrypt your private key files.The passphrase works with the key file to provide 2-factor authentication.For this example, we are leaving the passphrase empty.

Now you have a public/private ED25519 key pair(the .pub files are public keys and the rest are private keys):

Remember that private key files are the equivalent of a password should be protected the same way you protect your password.To help with that, use ssh-agent to securely store the private keys within a Windows security context, associated with your Windows login.To do that, start the ssh-agent service as Administrator and use ssh-add to store the private key.

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After completing these steps, whenever a private key is needed for authentication from this client, ssh-agent will automatically retrieve the local private key and pass it to your SSH client.

Note

It is strongly recommended that you back up your private key to a secure location,then delete it from the local system, after adding it to ssh-agent.The private key cannot be retrieved from the agent.If you lose access to the private key, you would have to create a new key pairand update the public key on all systems you interact with.

Deploying the public key

To use the user key that was created above, the public key needs to be placed on the server into a text file called authorized_keys under usersusername.ssh.The OpenSSH tools include scp, which is a secure file-transfer utility, to help with this.

To move the contents of your public key (~.sshid_ed25519.pub) into a text file called authorized_keys in ~.ssh on your server/host.

This example uses the Repair-AuthorizedKeyPermissions function in the OpenSSHUtils module which was previously installed on the host in the instructions above.

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These steps complete the configuration required to use key-based authentication with SSH on Windows.After this, the user can connect to the sshd host from any client that has the private key.