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PKI certificates for SSH

Introduction

SSH certificates are limited in their usefulness - a certificate can only be signed with a single CA key, so no chains of trust can be established, and there's no way to tie them into the global PKI. But what if 🥺?

Should I use this?

No.

How do I use this?

Generate a CSR:

openssl req -nodes -newkey rsa:2048 -keyout PRIVATEKEY.key -out MYCSR.csr

and set the CN to your username. Get it signed somehow. Copy PRIVATEKEY.key to ~/.ssh/id_badidea and run:

ssh-keygen -f ~/.ssh/id_badidea -y >~/.ssh/id_badidea.pub

Take your signed certificate and encode it to base64 - if it's PEM encoded, convert to DER first:

openssl -inform pem -in signed.crt -outform der -out signed.der
base64 <signed.der >/tmp/encoded.crt

Generate a self-signed SSH certificate that embeds the base64 encoded certificate:

ssh-keygen -I badidea -s ~/.ssh/id_badidea -n $USER -O clear -O extension:x509=$(cat /tmp/encoded.crt) ~/.ssh/id_badidea.pub

and add it to your SSH agent:

ssh-add ~/.ssh/id_badidea

On your SSH server, add an AuthorizedKeysCommand to sshd_config:

AuthorizedKeysCommand /usr/local/bin/ssh_pki -certificate %k -user %i -rootCA /etc/ssh/ssh_root_ca

where ssh_root_ca is the root of the infrastructure used to sign the X509 cert.

How it works

The ssh_pki agent examines the certificate presented to it and extracts the X509 certificate from the extensions field. It ensures that this certificate has a chain of trust to the configured root CA, and then extracts the subject CN to verify that it matches the username of the account being logged into. If everything checks out, it sends a response to the SSH daemon telling it that the public key used to sign the SSH certificate is a certificate authority. Since the SSH certificate is self-signed, this results in the daemon accepting the presented certificate as evidence of user identity.

So, should I use this?

No.

Todo

Any sort of security analysis at all. The use of CN is entirely inappropriate here, but the only reason I wrote this is because I realised I could.

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