OpenSSL is a crypto toolkit that has been around for thousands of years. Its first documented use was by Julius Caesar during the Gallic Wars when he developed his shift cipher.

This post is basically a cheat sheet, and it only covers a smattering of what is available.

Note that unless a filename is specified, these commands are interactive. Send EOF to the program (Ctrl-D) when done typing the message.

What version am I using?

$ openssl version
OpenSSL 1.1.0f  25 May 2017

Help!

$ openssl help

Encoding/Encrypting

Base64

Encode from stdin:

  $ openssl enc -base64
  foo
  Zm9vCg==

Decode from stdin:

  $ openssl enc -base64 -d
  Zm9vCg==
  foo

AES

Encrypt a file to encrypted.bin:

  $ openssl enc -aes-256-cbc -out encrypted.bin
  enter aes-256-cbc encryption password:
  Verifying - enter aes-256-cbc encryption password:
  hello, world!

Decrypt the file encrypted.bin:

  $ openssl enc -aes-256-cbc -d -in encrypted.bin
  enter aes-256-cbc decryption password:
  hello world!

Hashing

Useful for verifying downloads!

MD5

  $ > derp.txt echo foo
  $ openssl dgst -md5 derp.txt
  MD5(derp.txt)= d3b07384d113edec49eaa6238ad5ff00

  # Change the file to calculate a different hash!
  $ echo >> derp.txt
  $ openssl dgst -md5 derp.txt
  MD5(derp.txt)= dbb53f3699703c028483658773628452

SHA256

  $ > derp.txt echo foo
  $ openssl dgst -sha256 derp.txt
  SHA256(derp.txt)= b5bb9d8014a0f9b1d61e21e796d78dccdf1352f23cd32812f4850b878ae4944c

  # Change the file to calculate a different hash!
  $ echo >> derp.txt
  $ openssl dgst -sha256 derp.txt
  SHA256(derp.txt)= 37ea8ddde63ad9042aa7f5099db7acd2a880ae3012870c29060d4b12bf2dc2e2

Hashing Lengths

  $ openssl dgst -md5
  foo
  (stdin)= d3b07384d113edec49eaa6238ad5ff00
  $ openssl dgst -sha1
  foo
  (stdin)= f1d2d2f924e986ac86fdf7b36c94bcdf32beec15
  $ openssl dgst -sha256
  foo
  (stdin)= b5bb9d8014a0f9b1d61e21e796d78dccdf1352f23cd32812f4850b878ae4944c
  $ openssl dgst -sha512
  foo
  (stdin)= 0cf9180a764aba863a67b6d72f0918bc131c6772642cb2dce5a34f0a702f9470ddc2bf125c12198b1995c233c34b4afd346c54a2334c350a948a51b6e8b4e6b6

Benchmarking

To see how many checksums the computer can calculate, run the following for a particular algorithm (depends on CPU architecture, length of input, etc.):

  $ openssl speed sha
  $ openssl speed blowfish
  etc.

Public Key Cryptography

RSA

Generate a key pair:
  $ openssl genrsa -out key.pem 1024
  Generating RSA private key, 2048 bit long modulus
  .........+++
  ....................+++
  e is 65537 (0x010001)
Encrypt the private key (this example uses Triple DES, use whatever you want):
  $ openssl rsa -in key.pem -des3 -out enc-key.pem
  writing RSA key
  Enter PEM pass phrase:
  Verifying - Enter PEM pass phrase:
Extract the public key from the key pair:
  $ openssl rsa -in key.pem -pubout -out pub-key.pem
  writing RSA key
Encrypt a file:
  # This uses the key pair.
  $ openssl rsautl -encrypt -inkey key.pem -in data.txt -out encrypted.bin

  # This uses the public key (note the extra flag `-pubin`).
  $ openssl rsautl -encrypt -pubin -inkey pub-key.pem -in data.txt -out encrypted.bin
Note that the file to encrypt must be less than the block size, minus some extra bits used by the implementation. In our example, this is 1024 bits (the block size will be the same as what was specified as the key length). You will get an error if the file is larger than the block size.

OpenSSL is a low-level tool, and does not slice up your text into block sizes. This functionality is left to anything that implements the library.

Decrypt a file:
  # This uses the encrypted private key.
  $ openssl rsautl -decrypt -inkey enc-key.pem -in encrypted.bin -out decrypted.txt
  Enter pass phrase for enc-key.pem:
You can use the key pair to decrypt, but it won’t prompt you for a passphrase, as it’s not encrypted. Use the private key!

Digitally sign a file (two different methods):
Hash a digest of the file and sign that.
 # Create the hash.
 $ openssl dgst -sha1 -out foo.dgst foo.txt

 # Sign the hash.
 $ openssl rsautl -sign -in foo.dgst -out foo.sig -inkey enc-key.pem
 Enter pass phrase for enc-key.pem:
Sign the file itself.
 $ openssl rsautl -sign -in foo.txt -out foo.sig -inkey enc-key.pem
 Enter pass phrase for enc-key.pem:
Again, you can use the key pair to sign, but it won’t prompt you for a passphrase, as it’s not encrypted. Use the private key!

Verify the signature:
  $ openssl rsautl -verify -pubin -inkey pub-key.pem -in foo.sig -out verified.dgst
You’d then want to verify the hash if you signed using the first method above.

Get the fingerprint of a public key:
  $ ssh-keygen -lf <(ssh-keygen -yf private_key)
Note that this method avoids having to create a temporary file by using process substitution.

Fun

Using the key pair that we generated earlier, let’s look at the bits that make up the algorithm (the ellipsis notes where the values were truncated).
  $ openssl rsa -in key.pem -text -noout
  Private-Key: (2048 bit)
  modulus:
      00:c0:cd:8b:5b:a0:23:43:09:36:fa:e4:af:98:61:
      ...
  publicExponent: 65537 (0x10001)
  privateExponent:
      21:76:cb:9c:60:a4:1e:2b:88:46:6d:d0:e8:82:d9:
      ...
  prime1:
      00:e8:5c:64:aa:74:ae:fb:f9:af:e0:46:e5:82:1c:
      ...
  prime2:
      00:d4:6a:e7:13:2f:a2:d4:a9:b6:d3:9c:74:d9:f9:
      ...
  exponent1:
      15:af:29:a5:ce:a5:d5:d6:03:57:c6:c5:fc:52:6c:
      ...
  exponent2:
      00:c9:ad:f6:57:b1:12:d8:f7:8a:2e:c0:8d:f1:a7:
      ...
  coefficient:
      00:d6:9d:0a:5a:fe:9c:43:82:55:45:37:33:e8:5b:
      ...
This should make sense to those familiar with the RSA algorithm.

What number did OpenSSL generate for the modulus?:
  $ openssl rsa -in key.pem -modulus -noout
  Modulus=C0CD8B5BA023430936FAE4AF986118F86FD94B40FBFE7F2A57964EDD868F7BFD1351004B056719CFC470F26276570B32D247324F789990EA6CFC24061E377D4B6E6E4C899D0F5703B060EFCFEB9B8B7AEFBFD2ECBE7B75624DD7F9CBD203768B38E8938815D5641F50527D8DACB5F1C695A23DD3B998DE5511A706463D760C13
Let’s use our trusted friend bc to see what that number is in base 10!
  $ echo "ibase=16; $(openssl rsa -in key.pem -modulus -noout | cut -c9-)" | bc
  13539080606374968594676933696507556339553096890269217679724886472005\
  08050903637135355760972124160959413478394879173567838846759891805917\
  63282125770151505099501724487223049295609224541565594269213996582665\
  80150446659470901019777012489546440470891737027535564768871198696466\
  9536045975880720502650715976238500883
Wow, try factoring out those primes with pencil and paper!

Now that we have our two primes, let’s see if the product is our modulus! We’ll have to crack open our Unix tool kit to parse the output of OpenSSL.
Get the two primes.
 # Set the first prime as a shell variable.
 $ PRIME1=$(openssl rsa -in key.pem -text -noout |
 sed -n '/^prime/,/^prime/{/^prime/!p}' |
 xargs echo |
 xargs -I % echo "'" % "'.replace(/[\s:]/g, '').replace(/([a-f])/g, (a, b) => b.toUpperCase())" |
 node -p)

 # Set the second prime as a shell variable.
 $ PRIME2=$(openssl rsa -in key.pem -text -noout |
 sed -n '/^prime2/,/^exponent1/{/^prime2/!{/^exponent1/!p}}' |
 xargs echo |
 xargs -I % echo "'" % "'.replace(/[\s:]/g, '').replace(/([a-f])/g, (a, b) => b.toUpperCase())" |
 node -p)
Explanation of the (second) sed command:

/^prime2/,/^exponent1/ will match all the text between lines starting with prime2 and exponent1, inclusive.

/^prime2/! means execute the following command if start of line is not prime2.

/^exponent1/! means execute the following command if start of line is not exponent1.

p means print (the command to execute).

Note that this sed command won’t work on Mac. The BSD command line tools are different from the GNU/Linux ones in subtle ways, so you’ll need to use the gsed binary instead (or not, it depends on the presence of the install flag --with-default-names).

( You may need to add semicolons before the closing brackets, but I have not been able to test this. )
Calculate the product of our two primes:
 $ echo "ibase=16; $PRIME1 * $PRIME2" | bc
 13539080606374968594676933696507556339553096890269217679724886472005\
 08050903637135355760972124160959413478394879173567838846759891805917\
 63282125770151505099501724487223049295609224541565594269213996582665\
 80150446659470901019777012489546440470891737027535564768871198696466\
 9536045975880720502650715976238500883
Since the primes are in hex format, we must specify ibase=16.

That looks sneakily like the modulus that openssl reported in a prior command.
  $ echo "ibase=16; $(openssl rsa -in key.pem -modulus -noout | cut -c9-) == $PRIME1 * $PRIME2" | bc
  1
It is! So what does that prove? Math! Weeeeeeeeeeeeeeeeeee.

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