The recent release of OpenSSH 6.5 had many convincing new features to make me update to it early, quoting from the release notes:
- support for key exchange using elliptic-curve Diffie–Hellman in Daniel Bernstein’s Curve25519
- support for Ed25519 as a public key type
- a new private key format that uses a bcrypt KDF to better protect keys at rest
- a new transport cipher
email@example.com combines Daniel Bernstein’s ChaCha20 stream cipher and Poly1305 MAC to build an authenticated encryption mode
Since OpenSSH 5.7, there is support for ECDSA keys according to RFC5656. The problem with this schema is that it uses NIST curves generally. Due to recent events, everyone is (rightfully) more paranoid now, and there are reasons to consider these curves to be problematic. Thus, I decided to disable support for ECDSA host keys and use the superior ED25519 scheme for new keys.
However, I also need to access many machines which don’t run the latest version of OpenSSH, but for these we can at least make use of the new, safer public key format.
First, I will show how to update your OpenSSH installation to make use of the new features, and then I’ll explain what else I had to do to make everything work correctly.
Arch is, at the time of writing, providing binaries in “testing”, but plucking a single package is easy:
# pacman -U http://mirror.de.leaseweb.net/archlinux/testing/os/x86_64/openssh-6.5p1-1-x86_64.pkg.tar.xz
After merging configuration files (if required), we edit
/etc/ssh/sshd_config and spell out the
HostKeys to disable the
built-in defaults, which include ECDSA.
HostKey /etc/ssh/ssh_host_rsa_key HostKey /etc/ssh/ssh_host_dsa_key HostKey /etc/ssh/ssh_host_ed25519_key
Upon restarting SSH, a new ED25519 hostkey will be generated. Using ignite:
# sv restart sshd
Essentially, that’s it. Let’s check that the ECDSA hostkey is disabled:
% ssh-keyscan -t ecdsa,ed25519 localhost # localhost SSH-2.0-OpenSSH_6.5 no hostkey alg # localhost SSH-2.0-OpenSSH_6.5 localhost ssh-ed25519 AAAA...
(AFAIU, ECDSA user keys in
authorized_keys will still work. It’s
your task to replace them with ED22519 ones, I have found no way to
We continue by creating a new ED25519 key for the user:
% ssh-keygen -t ed25519 Generating public/private ed25519 key pair. Enter file in which to save the key (/home/chris/.ssh/id_ed25519): Enter passphrase (empty for no passphrase): Enter same passphrase again: ...
For testing, we can add it to the locally accepted keys:
% cat .ssh/id_ed25519.pub >>.ssh/authorized_keys
Finally, we can test it:
% ssh chris@localhost Enter passphrase for key '/home/chris/.ssh/id_ed25519':
It seems to work! (Perhaps you’ll see an update of the fingerprint if
you had the ECDSA one saved in
I was happy about that until I realized that
ssh asked for the
passphrase, and not my
gnome-keyring-daemon… which brings us to
part two of this post.
Migrating to ssh-agent and the IdentityPersist patch
Since new ED25519 keys are always stored in the new bcrypt format,
they won’t work (as of right now) with SSH agents that don’t support
it (I know of
the key itself, anyway). Essentially, only plain
it, but I used to hate
ssh-agent since it doesn’t support adding
keys upon use:
gnome-keyring will ask for the password and keep the
key unlocked. Since I try to keep my keys
when I’m not using them, I don’t want to keep them unlocked in every
session, and neither unlock them manually, because that is
Luckily, I found this
patch which adds
the key automatically. I hope it gets accepted, because it is very
useful. I couldn’t wait and patched OpenSSH
With this tiny patch, I could finally drop my use of
which is one more step towards a GTK3-free desktop.
ssh-agent from my
eval $(ssh-agent -s) xscreensaver-ssh-helper &
Now, we can convert our old keys to the new storage format:
% ssh-keygen -p -o -f ~/.ssh/id_dsa Enter old passphrase: Key has comment 'id_dsa' Enter new passphrase (empty for no passphrase): Enter same passphrase again: Your identification has been saved with the new passphrase.
The key file should now start with
-----BEGIN OPENSSH PRIVATE KEY-----.
The public key format is unchanged.
For the IdentityPersist patch, we need to add a line to
stating the lifetime of the key (or
true for infinity):
Now, we can try everything together:
% ssh myhost Enter passphrase for key '/home/chris/.ssh/id_dsa': Identity added: /home/chris/.ssh/id_dsa (id_dsa) ...
Another SSH connect within the next 5 minutes will connect without asking for a password.
I noticed one more difference between
gnome-keyring would unlock any key that has a
ssh-agent requires an explicit list in
IdentityFile ~/.ssh/id_ed25519 IdentityFile ~/.ssh/id_dsa IdentityFile ~/.ssh/id_work
I had one final issue, which is rather niche: My newsreader
connects to my NNTP feed via a SSH hop. The configuration looked like this:
(setq gnus-select-method '(nntp "localhost" (nntp-address "myshellhost") (nntp-rlogin-program "ssh") (nntp-open-connection-function nntp-open-rlogin) (nntp-end-of-line "\n") (nntp-rlogin-parameters ("nc" "mynntpserver" "nntp"))))
A configuration like this will fail, because Emacs runs this
process with a
pty, and there
ssh will stupidly ask for the
password to unlock (if required). But I learned this
configuration is outdated anyway, and the recommended version using
nntp-open-via-rlogin-and-netcat works correctly, and asks for the
password (if required) using
x11-ask-sshpass. This is mentioned in
a comment in
nntp.el, so I’m not the first on to stumble on this.
A fixed version of above would be:
(setq gnus-select-method '(nntp "localhost" (nntp-address "mynntpserver") (nntp-via-address "myshellserver") (nntp-via-rlogin-command "ssh") (nntp-via-rlogin-command-switches ("-C")) (nntp-open-connection-function nntp-open-via-rlogin-and-netcat)))
Enjoy your safer OpenSSH setup!