I'm writing a book for O'Reilly, called Designing Data-Intensive Applications.
Entrepreneurship, web technology and the user experience
Ever wondered how those key files in
~/.ssh actually work? How secure are they actually?
As you probably do too, I use ssh many times every single day — every
git fetch and
git push, every deploy, every login to a server. And recently I realised that to me, ssh was just some crypto voodoo that I had become accustomed to using, but I didn’t really understand. That’s a shame — I like to know how stuff works. So I went on a little journey of discovery, and here are some of the things I found.
When you start reading about “crypto stuff”, you very quickly get buried in an avalanche of acronyms. I will briefly mention the acronyms as we go along; they don’t help you understand the concepts, but they are useful in case you want to Google for further details.
Quick recap: If you’ve ever used public key authentication, you probably have a file
~/.ssh/id_dsa in your home directory. This is your RSA/DSA private key, and
~/.ssh/id_dsa.pub is its public key counterpart. Any machine you want to log in to needs to have your public key in
~/.ssh/authorized_keys on that machine. When you try to log in, your SSH client uses a digital signature to prove that you have the private key; the server checks that the signature is valid, and that the public key is authorized for your username; if all is well, you are granted access.
So what is actually inside this private key file?
Everyone recommends that you protect your private key with a passphrase (otherwise anybody who steals the file from you can log into everything you have access to). If you leave the passphrase blank, the key is not encrypted. Let’s look at this unencrypted format first, and consider passphrase protection later.
A ssh private key file typically looks something like this:
-----BEGIN RSA PRIVATE KEY----- MIIEogIBAAKCAQEArCQG213utzqE5YVjTVF5exGRCkE9OuM7LCp/FOuPdoHrFUXk y2MQcwf29J3A4i8zxpES9RdSEU6iIEsow98wIi0x1/Lnfx6jG5Y0/iQsG1NRlNCC aydGvGaC+PwwWiwYRc7PtBgV4KOAVXMZdMB5nFRaekQ1ksdH/360KCGgljPtzTNl 09e97QBwHFIZ3ea5Eih/HireTrRSnvF+ywmwuxX4ubDr0ZeSceuF2S5WLXH2+TV0 ... etc ... lots of base64 blah blah ... -----END RSA PRIVATE KEY-----
The private key is an ASN.1 data structure, serialized to a byte string using DER, and then Base64-encoded. ASN.1 is roughly comparable to JSON (it supports various data types such as integers, booleans, strings and lists/sequences that can be nested in a tree structure). It’s very widely used for cryptographic purposes, but it has somehow fallen out of fashion with the web generation (I don’t know why, it seems like a pretty decent format).
$ ssh-keygen -t rsa -N '' -f test_rsa_key $ openssl asn1parse -in test_rsa_key 0:d=0 hl=4 l=1189 cons: SEQUENCE 4:d=1 hl=2 l= 1 prim: INTEGER :00 7:d=1 hl=4 l= 257 prim: INTEGER :C36EB2429D429C7768AD9D879F98C... 268:d=1 hl=2 l= 3 prim: INTEGER :010001 273:d=1 hl=4 l= 257 prim: INTEGER :A27759F60AEA1F4D1D56878901E27... 534:d=1 hl=3 l= 129 prim: INTEGER :F9D23EF31A387694F03AD0D050265... 666:d=1 hl=3 l= 129 prim: INTEGER :C84415C26A468934F1037F99B6D14... 798:d=1 hl=3 l= 129 prim: INTEGER :D0ACED4635B5CA5FB896F88BB9177... 930:d=1 hl=3 l= 128 prim: INTEGER :511810DF9AFD590E11126397310A6... 1061:d=1 hl=3 l= 129 prim: INTEGER :E3A296AE14E7CAF32F7E493FDF474...
DSA keys are similar, a sequence of six integers:
$ ssh-keygen -t dsa -N '' -f test_dsa_key $ openssl asn1parse -in test_dsa_key 0:d=0 hl=4 l= 444 cons: SEQUENCE 4:d=1 hl=2 l= 1 prim: INTEGER :00 7:d=1 hl=3 l= 129 prim: INTEGER :E497DFBFB5610906D18BCFB4C3CCD... 139:d=1 hl=2 l= 21 prim: INTEGER :CF2478A96A941FB440C38A86F22CF... 162:d=1 hl=3 l= 129 prim: INTEGER :83218C0CA49BA8F11BE40EE1A7C72... 294:d=1 hl=3 l= 128 prim: INTEGER :16953EA4012988E914B466B9C37CB... 425:d=1 hl=2 l= 21 prim: INTEGER :89A356E922688EDEB1D388258C825...
Next, in order to make life harder for an attacker who manages to steal your private key file, you protect it with a passphrase. How does this actually work?
$ ssh-keygen -t rsa -N 'super secret passphrase' -f test_rsa_key $ cat test_rsa_key -----BEGIN RSA PRIVATE KEY----- Proc-Type: 4,ENCRYPTED DEK-Info: AES-128-CBC,D54228DB5838E32589695E83A22595C7 3+Mz0A4wqbMuyzrvBIHx1HNc2ZUZU2cPPRagDc3M+rv+XnGJ6PpThbOeMawz4Cbu lQX/Ahbx+UadJZOFrTx8aEWyZoI0ltBh9O5+ODov+vc25Hia3jtayE51McVWwSXg wYeg2L6U7iZBk78yg+sIKFVijxiWnpA7W2dj2B9QV0X3ILQPxbU/cRAVTd7AVrKT ... etc ... -----END RSA PRIVATE KEY-----
We’ve gained two header lines, and if you try to parse that Base64 text, you’ll find it’s no longer valid ASN.1. That’s because the entire ASN.1 structure we saw above has been encrypted, and the Base64-encoded text is the output of the encryption. The header tells us the encryption algorithm that was used: AES-128 in CBC mode. The 128-bit hex string in the
DEK-Info header is the initialization vector (IV) for the cipher. This is pretty standard stuff; all common crypto libraries can handle it.
But how do you get from the passphrase to the AES encryption key? I couldn’t find it documented anywhere, so I had to dig through the OpenSSL source to find it:
That’s it. To prove it, let’s decrypt the private key manually (using the IV/salt from the
DEK-Info header above):
$ tail -n +4 test_rsa_key | grep -v 'END ' | base64 -D | # get just the binary blob openssl aes-128-cbc -d -iv D54228DB5838E32589695E83A22595C7 -K $( ruby -rdigest/md5 -e 'puts Digest::MD5.hexdigest(["super secret passphrase",0xD5,0x42,0x28,0xDB,0x58,0x38,0xE3,0x25].pack("a*cccccccc"))' ) | openssl asn1parse -inform DER
…which prints out the sequence of integers from the RSA key in the clear. Of course, if you want to inspect the key, it’s much easier to do this:
$ openssl rsa -text -in test_rsa_key -passin 'pass:super secret passphrase'
but I wanted to demonstrate exactly how the AES key is derived from the password. This is important because the private key protection has two weaknesses:
If your private SSH key ever gets into the wrong hands, e.g. because someone steals your laptop or your backup hard drive, the attacker can try a huge number of possible passphrases, even with moderate computing resources. If your passphrase is a dictionary word, it can probably be broken in a matter of seconds.
That was the bad news: the passphrase on your SSH key isn’t as useful as you thought it was. But there is good news: you can upgrade to a more secure private key format, and everything continues to work!
What we want is to derive a symmetric encryption key from the passphrase, and we want this derivation to be slow to compute, so that an attacker needs to buy more computing time if they want to brute-force the passphrase. If you’ve seen the use bcrypt meme, this should sound very familiar.
For SSH private keys, there are a few standards with clumsy names (acronym alert!) that can help us out:
I don’t know why
ssh-keygen still generates keys in SSH’s traditional format, even though a better format has been available for years. Compatibility with servers is not a concern, because the private key never leaves your machine. Fortunately it’s easy enough to convert to PKCS#8:
$ mv test_rsa_key test_rsa_key.old $ openssl pkcs8 -topk8 -v2 des3 \ -in test_rsa_key.old -passin 'pass:super secret passphrase' \ -out test_rsa_key -passout 'pass:super secret passphrase'
If you try using this new PKCS#8 file with a SSH client, you should find that it works exactly the same as the file generated by
ssh-keygen. But what’s inside it?
$ cat test_rsa_key -----BEGIN ENCRYPTED PRIVATE KEY----- MIIFDjBABgkqhkiG9w0BBQ0wMzAbBgkqhkiG9w0BBQwwDgQIOu/S2/v547MCAggA MBQGCCqGSIb3DQMHBAh4q+o4ELaHnwSCBMjA+ho9K816gN1h9MAof4stq0akPoO0 CNvXdtqLudIxBq0dNxX0AxvEW6exWxz45bUdLOjQ5miO6Bko0lFoNUrOeOo/Gq4H dMyI7Ot1vL9UvZRqLNj51cj/7B/bmfa4msfJXeuFs8jMtDz9J19k6uuCLUGlJscP ... etc ... -----END ENCRYPTED PRIVATE KEY-----
Notice that the header/footer lines have changed (
BEGIN ENCRYPTED PRIVATE KEY instead of
BEGIN RSA PRIVATE KEY), and the plaintext
DEK-Info headers have gone. In fact, the whole key file is once again a ASN.1 structure:
$ openssl asn1parse -in test_rsa_key 0:d=0 hl=4 l=1294 cons: SEQUENCE 4:d=1 hl=2 l= 64 cons: SEQUENCE 6:d=2 hl=2 l= 9 prim: OBJECT :PBES2 17:d=2 hl=2 l= 51 cons: SEQUENCE 19:d=3 hl=2 l= 27 cons: SEQUENCE 21:d=4 hl=2 l= 9 prim: OBJECT :PBKDF2 32:d=4 hl=2 l= 14 cons: SEQUENCE 34:d=5 hl=2 l= 8 prim: OCTET STRING [HEX DUMP]:3AEFD2DBFBF9E3B3 44:d=5 hl=2 l= 2 prim: INTEGER :0800 48:d=3 hl=2 l= 20 cons: SEQUENCE 50:d=4 hl=2 l= 8 prim: OBJECT :des-ede3-cbc 60:d=4 hl=2 l= 8 prim: OCTET STRING [HEX DUMP]:78ABEA3810B6879F 70:d=1 hl=4 l=1224 prim: OCTET STRING [HEX DUMP]:C0FA1A3D2BCD7A80DD61F4C0287F8B2D...
Sequence (2 elements) |- Sequence (2 elements) | |- Object identifier: 1.2.840.1135184.108.40.206 // using PBES2 from PKCS#5 | `- Sequence (2 elements) | |- Sequence (2 elements) | | |- Object identifier: 1.2.840.1135220.127.116.11 // using PBKDF2 -- yay! :) | | `- Sequence (2 elements) | | |- Byte string (8 bytes): 3AEFD2DBFBF9E3B3 // salt | | `- Integer: 2048 // iteration count | `- Sequence (2 elements) | Object identifier: 1.2.840.113549.3.7 // encrypted with Triple DES, CBC | Byte string (8 bytes): 78ABEA3810B6879F // initialization vector `- Byte string (1224 bytes): C0FA1A3D2BCD7A80DD61F4C0287F8B2DAB46A43E... // encrypted key blob
The format uses OIDs, numeric codes allocated by a registration authority to unambiguously refer to algorithms. The OIDs in this key file tell us that the encryption scheme is pkcs5PBES2, that the key derivation function is PBKDF2, and that the encryption is performed using des-ede3-cbc. The hash function can be explicitly specified if needed; here it’s omitted, which means that it defaults to hMAC-SHA1.
The nice thing about having all those identifiers in the file is that if better algorithms are invented in future, we can upgrade the key file without having to change the container file format.
You can also see that the key derivation function uses an iteration count of 2,048. Compared to just one iteration in the traditional SSH key format, that’s good — it means that it’s much slower to brute-force the passphrase. The number 2,048 is currently hard-coded in OpenSSL; I hope that it will be configurable in future, as you could probably increase it without any noticeable slowdown on a modern computer.
If you already have a strong passphrase on your SSH private key, then converting it from the traditional private key format to PKCS#8 is roughly comparable to adding two extra keystrokes to your passphrase, for free. And if you have a weak passphrase, you can take your private key protection from “easily breakable” to “slightly harder to break”.
It’s so easy, you can do it right now:
$ mv ~/.ssh/id_rsa ~/.ssh/id_rsa.old $ openssl pkcs8 -topk8 -v2 des3 -in ~/.ssh/id_rsa.old -out ~/.ssh/id_rsa $ chmod 600 ~/.ssh/id_rsa # Check that the converted key works; if yes, delete the old one: $ rm ~/.ssh/id_rsa.old
openssl pkcs8 command asks for a passphrase three times: once to unlock your existing private key, and twice for the passphrase for the new key. It doesn’t matter whether you use a new passphrase for the converted key or keep it the same as the old key.
Not all software can read the PKCS8 format, but that’s fine — only your SSH client needs to be able to read the private key, after all. From the server’s point of view, storing the private key in a different format changes nothing at all.
On Mac OS X 10.9 (Mavericks), the default installation of OpenSSH no longer supports PKCS#8 private keys for some reason. If you followed the instructions above, you may no longer be able to log into your servers. Fortunately, it’s easy to convert your private key from PKCS#8 format back into the traditional key format:
$ mv ~/.ssh/id_rsa ~/.ssh/id_rsa.pkcs8 $ openssl pkcs8 -in ~/.ssh/id_rsa.pkcs8 -out ~/.ssh/id_rsa $ chmod 600 ~/.ssh/id_rsa $ ssh-keygen -f ~/.ssh/id_rsa -p
openssl command decrypts the key, and the
ssh-keygen command re-encrypts it using the traditional SSH key format.