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This weekend I installed the Windows 10 Spring Update, and was pretty excited to start playing with the new, builtin OpenSSH tools.

How to generate an SSH key in Windows 10. Windows will now generate your RSA public/private key pair. The public key will be stored as “idrsa.pub” in the directory you specified. Windows 10 SSH keys. To save the private key in the openssh format, go to Conversions-Export OpenSSH key ( if you did not define a passkey it will ask you to.

Using OpenSSH natively in Windows is awesome since Windows admins no longer need to use Putty and PPK formatted keys. I started poking around and reading up more on what features were supported, and was pleasantly surprised to see ssh-agent.exe is included.

I found some references to using the new Windows ssh-agent in this MSDN article, and this part immediately grabbed my attention:

I’ve had some good fun in the past with hijacking SSH-agents, so I decided to start looking to see how Windows is “securely” storing your private keys with this new service.

I’ll outline in this post my methodology and steps to figuring it out. This was a fun investigative journey and I got better at working with PowerShell.

tl;dr

Private keys are protected with DPAPI and stored in the HKCU registry hive. I released some PoC code here to extract and reconstruct the RSA private key from the registry

The first thing I tested was using the OpenSSH utilities normally to generate a few key-pairs and adding them to the ssh-agent.

First, I generated some password protected test key-pairs using ssh-keygen.exe:

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Then I made sure the new ssh-agent service was running, and added the private key pairs to the running agent using ssh-add:

Running ssh-add.exe -L shows the keys currently managed by the SSH agent.

Finally, after adding the public keys to an Ubuntu box, I verified that I could SSH in from Windows 10 without needing the decrypt my private keys (since ssh-agent is taking care of that for me):

To figure out how the SSH Agent was storing and reading my private keys, I poked around a little and started by statically examining ssh-agent.exe. My static analysis skills proved very weak, however, so I gave up and just decided to dynamically trace the process and see what it was doing.

I used procmon.exe from Sysinternals and added a filter for any process name containing “ssh”.

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With procmon capturing events, I then SSH’d into my Ubuntu machine again. Looking through all the events, I saw ssh.exe open a TCP connection to Ubuntu, and then finally saw ssh-agent.exe kick into action and read some values from the Registry:

Two things jumped out at me:

The process ssh-agent.exe reads values from HKCUSoftwareOpenSSHAgentKeys
After reading those values, it immediately opens dpapi.dll

Just from this, I now knew that some sort of protected data was being stored in and read from the Registry, and ssh-agent was using Microsoft’s Data Protection API

Sure enough, looking in the Registry, I could see two entries for the keys I added using ssh-add. The key names were the fingerprint of the public key, and a few binary blobs were present:

After reading StackOverflow for an hour to remind myself of PowerShell’s ugly syntax (as is tradition), I was able to pull the registry values and manipulate them. The “comment” field was just ASCII encoded text and was the name of the key I added:

The (default) value was just a byte array that didn’t decode to anything meaningful. I had a hunch this was the “encrypted” private key if I could just pull it and figure out how to decrypt it. I pulled the bytes to a Powershell variable:

I wasn’t very familiar with DPAPI, although I knew a lot of post exploitation tools abused it to pull out secrets and credentials, so I knew other people had probably implemented a wrapper. A little Googling found me a simple oneliner by atifaziz that was way simpler than I imagined (okay, I guess I see why people like Powershell…. ;) )

Someone in darkness download game mega. I still had no idea whether this would work or not, but I tried to unprotect the byte array using DPAPI. I was hoping maybe a perfectly formed OpenSSH private key would just come back, so I base64 encoded the result:

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The Base64 returned didn’t look like a private key, but I decoded it anyway just for fun and was very pleasantly surprised to see the string “ssh-rsa” in there! I had to be on the right track.

This part actually took me the longest. I knew I had some sort of binary representation of a key, but I could not figure out the format or how to use it.

I messed around generating various RSA keys with openssl, puttygen and ssh-keygen, but never got anything close to resembling the binary I had. List of key items in generation vii.

Finally after much Googling, I found an awesome blogpost from NetSPI about pulling out OpenSSH private keys from memory dumps of ssh-agent on Linux: https://blog.netspi.com/stealing-unencrypted-ssh-agent-keys-from-memory/

Could it be that the binary format is the same? I pulled down the Python script linked from the blog and fed it the unprotected base64 blob I got from the Windows registry:

It worked! I have no idea how the original author soleblaze figured out the correct format of the binary data, but I am so thankful he did and shared. All credit due to him for the awesome Python tool and blogpost.

After I had proved to myself it was possible to extract a private key from the registry, I put it all together in two scripts.

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The first is a Powershell script (extract_ssh_keys.ps1) which queries the Registry for any saved keys in ssh-agent. It then uses DPAPI with the current user context to unprotect the binary and save it in Base64. Since I didn’t even know how to start parsing Binary data in Powershell, I just saved all the keys to a JSON file that I could then import in Python. The Powershell script is only a few lines:

I heavily borrowed the code from parse_mem_python.py by soleblaze and updated it to use Python3 for the next script: extractPrivateKeys.py. Feeding the JSON generated from the Powershell script will output all the RSA private keys found:

These RSA private keys are unencrypted. Even though when I created them I added a password, they are stored unencrypted with ssh-agent so I don’t need the password anymore.

To verify, I copied the key back to a Kali linux box and verified the fingerprint and used it to SSH in!

Next Steps

Obviously my PowerShell-fu is weak and the code I’m releasing is more for PoC. It’s probably possible to re-create the private keys entirely in PowerShell. I’m also not taking credit for the Python code - that should all go to soleblaze for his original implementation.

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I would also love to eventually see this weaponized and added to post-exploitation frameworks since I think we will start seeing a lot more OpenSSH usage on Windows 10 by administrators and I’m sure these keys could be very valuable for redteamers and pentesters :)

Feedback and comments welcome!

Enjoy-ropnop

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,

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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:

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

User key generation

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.

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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.

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.

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

Backyard baseball scummvm download mac. 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.

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