Shhh — Your Encryption Best Friend

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shhh is little program that makes it trivial to encrypt and decrypt sensitive data. But, unlike many other existing tools, shhh's goal is to dramatically simplify the command line interface (CLI), and make symmetric encryption as routine as listing directories in Terminal.

With this tool I wanted to make it easy to memorize the most common options, so that there is little no longer a barrier to the full power of encryption offered by OpenSSL library.

And no tool works in isolation: this is just a stepping stone that could be part of your deployment or infrastructure code: don't rely on external services: minimize the risk of a "man-in-the-middle" attack, by dealing with the encryption and decryption locally. Ideal application of this gem, is the ability to store sensitive application secrets protected on a file system, or in a repo, and use shhh to automaticaly decrypt the data when any changes are to be made, or when the data needs to be read by an application service.

And finally, in addition to the rich CLI interface of the shhh executable, there is a rich and extensibe symmetric encryption API that can be easily used from any ruby project.

How It Works

  1. You start with a piece of sensitive data, say it's called X.
  2. X is currently a file on your file system, unencrypted.
  3. You use shhh (with -g — for "generate") to make a new encryption key. The key is 256 bits, or 32 bytes, or 45 bytes when base64-encoded.
  4. You must save this key somewhere safe. We'll talk about this further.
  5. You use shhh (with -e) to encrypt X with the key, and save into Y.
  6. You now delete X from your file system. You now only have Y and the key.
  7. To read the data back, you use shhh with the -d (for "decrypt") to decrypt Y back. You can print the contents or save it again.
  8. But, instead of just decrypting it, you can use the -t mode (for "ediT"), which would decrypt Y into X, save X into a temporary location, and allow you to edit the unencrypted file using $EDITOR. Once you save and exit the editor, a new version is automatically encrypted and replaces the old version, showing you the diff and, optionally, creating a backup.


The shhh executable as well as the Ruby API provide:

  • Symmetric data encryption with:
    • the cipher AES-256-CBC used by the US Government
    • 256-bit private key
      • which can be auto-generated, and is a base64-encoded string which is 45 characters long. The decoded secret is always 32 characters long (or 256 bytes long).
      • which can be optionally password-encrypted using 128-bit key.
      • which is automatically detected when the key is read
  • Rich command line interface with some innovative features, such as inline editing of an encrypted file, using your favorite $EDITOR.
  • Data handling:
    • Automatic compression of the data upon encryption
    • Automatic base64 encryption to make all encrypted strings fit onto a single line.
    • This makes the format suitable for YAML or JSON configuration files, where only the values are encrypted.
  • Rich Ruby API
  • (OS-X Only): Ability to create, add and delete generic password entries from the Mac OS-X KeyChain, and to leverage the KeyChain to store sensitive private keys.

Symmetric Encryption

Symmetric encryption simply means that we are using the same private key to encrypt and decrypt. In addition to the private key, the encryption uses an IV vector. The library completely hides iv from the user, generates one random iv per encryption, and stores it together with the field itself (base64-encoded).


If you plan on using the library in your ruby project with Bundler managing its dependencies, just include the following line in your Gemfile:

gem 'shhh'

And then run bundle.

Or install it into the global namespace with gem install command:

$ gem install shhh
$ shhh -h
$ shhh -E # see examples

BASH Completion (Optional Step)

After gem installation, an message will tell you to install a shown BASH script to your ~/.bashrc or equivalent.

Should you choose to install it (this part is optional), you will be able to use "tab-tab" after typing shhh and you'll be able to choose from all supported flags.


Private Keys

This library relies on the existance of the 32-byte private key (aka, a secret) to perform encryption and decryption.

The key can be easily:

  • generated by this gem and displayed, copied to the clipboard, or saved to the KeyChain
  • one way or another must be kept very well protected and secure from attackers
  • can be fetched from the the Keychain in subsequent encryption/decryption steps
  • password-protected, which you can enable during the generation with the -p flag.
    • NOTE: right now there is no way to add a password to an existing key, only generate a new one.

Unencrypted private key will be in the form of a base64-encoded string, 45 characters long.

Encrypted private key will be considerably longer, perhaps 200-300 characters long.

When the private key is encrypted, shhh will request the password every time it is used. We are looking at adding a caching layer with a configuerable timeout, so that the password is only re-entered once per given period.

Command Line (CLI)

You can generate using the command line, or in a programmatic way. First we'll discuss the command line usage, and in a later section we'll discuss Ruby API provided by the gem.

Generating and Using Private Keys

Once the gem is installed you will be able to run an executable shhh. Now let's generate and copy the new private key to the clipboard. Clipboard copy is activated with the -c flag:

shhh -gc

Or save a new key into a bash variable

SECRET=$(shhh -g)

Or save it to a file:

shhh -go ~/.key

Or create a password-protected key, and save it to a file:

shhh -gcp -o ~/.secret
# New Password:     ••••••••••
# Confirm Password: ••••••••••

You can subsequently use the private key by either:

  1. passing the -k [key value] flag
  2. passing the -K [key file] flag3.
  3. pasting or typing the key with the -i (interactive) flag
  4. passing the -x [keychain access entry name] flag to read from Mac OS-X KeyChain Access's generic password field.

Using KeyChain Access on Mac OS-X

On Mac OS-X there is a third option – using the Keychain Access Manager behind the scenes. Apple released a security command line tool, which this library uses to securely store a key/value pair of the key name and the actual private key in your OS-X KeyChain. The advantages of this method are numerous:

  • The private key won't be lying around your file system unencrypted, so if your Mac is ever stolen, you don't need to worry about the keys running wild.
  • If you sync your keychain with iCloud you will have access to it on other machines

To activate the KeyChain mode on the Mac, use -x <keyname> field instead of -k or -K, and add it to -g when generating a key. The keyname is what you name this particular key base on where it's going to be used. For example, you may call it staging, etc.

The following command generates the private key and immediately stores it in the KeyChain access under the name provided:

shhh -g -x staging

Now, whenever you need to encrypt something, in addition to the -k and -K you can also choose -x staging. This will retrieve the key from the KeyChain access, and use it for encryption/decryption.

Finally, you can delete a key from KeyChain access by running:

shhh --keychain-del staging

KeyChain Key Management

Another tiny executable supplied with this library is called keychain

Usage: keychain item [ add <contents> | find | delete ]

You can use this to add an existing key that can be used with the shhh later. Of course you can also use the tool to find or delete it.

Encryption and Decryption

This may be a good time to take a look at the full help message for the shhh tool, shown naturally with a -h or --help option.

Shhh (1.6.1) – encrypt/decrypt data with a private key

   # Generate a new key:
   shhh -g [ -c ] [ -p ] [ -x keychain ] [ -o keyfile | -q | ]  

   # Encrypt/Decrypt 
   shhh [ -d | -e ] [ -f <file> | -s <string> ] 
        [ -k key | -K keyfile | -x keychain | -i ] 
        [ -o <output file> ] 

   # Edit an encrypted file in $EDITOR 
   shhh -t -f <file> [ -b ][ -k key | -K keyfile | -x keychain | -i ] 

  -e, --encrypt                 encrypt mode
  -d, --decrypt                 decrypt mode
  -t, --edit                    edit an encrypted file in an $EDITOR

Create a private key:
  -g, --generate                generate a new private key
  -p, --password                encrypt the key with a password
  -c, --copy                    copy the new key to the clipboard
  -x, --keychain     [key-name] add to (or read from) the OS-X Keychain

Provide a private key:
  -i, --interactive             Paste or type the key interactively
  -k, --private-key  [key]      private key as a string
  -K, --keyfile      [key-file] private key from a file

  -s, --string       [string]   specify a string to encrypt/decrypt
  -f, --file         [file]     filename to read from
  -o, --output       [file]     filename to write to

  --keychain-del     [key-name] delete keychain entry with that name
  -b, --backup                  create a backup file in the edit mode
  -v, --verbose                 show additional information
  -T, --trace                   print a backtrace of any errors
  -q, --quiet                   silence all output
  -V, --version                 print library version
  -N, --no-color                disable color output

Help & Examples:
  -E, --examples                show several examples
  -L, --language                natural language examples
  -h, --help                    show help

CLI Usage Examples

Generating the Key:

Generate a new private key into an environment variable:

export KEY=$(shhh -g)
echo $KEY
# => 75ngenJpB6zL47/8Wo7Ne6JN1pnOsqNEcIqblItpfg4=

Generate a new password-protected key, copy to the clipboard & save to a file:

shhh -gpc -o ~/.key
New Password     : ••••••••••
Confirm Password : ••••••••••

Encrypt a plain text string with a key, and save the output to a file:

shhh -e -s "secret string" -k $KEY -o file.enc
cat file.enc
# => Y09MNDUyczU1S0UvelgrLzV0RTYxZz09CkBDMEw4Q0R0TmpnTm9md1QwNUNy%T013PT0K

Decrypt a previously encrypted string:

shhh -d -s $(cat file.enc) -k $KEY
# => secret string

Encrypt a file and save it to shhh.enc:

shhh -e -f app-shhh.yml -o app-shhh.enc -k $KEY

Decrypt an encrypted file and print it to STDOUT:

shhh -df app-shhh.enc -k $KEY
Inline Editing

The shhh CLI tool supports one interesting mode where you can open an encrypted file in an $EDITOR, and edit it's unencrypted version (stored temporarily in a temp file), and upon saving and exiting the gem will automatically diff the new and old content, and if different – will save encrypt it and overwrite the original file.

In this mode several flags are of importance:

-b (--backup)   – will create a backup of the original file
-v (--verbose) - will show additional info about file sizes

Here is a full command that opens a file specified by -f | --file, using the key specified in -K | --keyfile, in the editor defined by the $EDITOR environment variable (or if not set – defaults to /bin/vi)".

NOTE: while much effort has been made to ensure that the gem is bug free, the reality is that no software is bug free. Please make sure to backup your encrypted file before doing it for the first few times to get familiar with the command.

To edit an encrypted file in $EDITOR, while asking to paste the key (-i | --interactive), while creating a backup file (-b | --backup):

shhh -tibf data.enc
# => Private Key: ••••••••••••••••••••••••••••••••••••••••••••
# => Diff:
# 3c3
# # (c) 2015 Konstantin Gredeskoul.  All rights reserved.
# ---
# # (c) 2016 Konstantin Gredeskoul.  All rights reserved.

Natural Language Processing

When shhh is invoked, and the first argument does not begin with a dash, then the the NLP (natural language processing) Translator is invoked. The Translator is based on a very simple algorithm:

  • ignore any of the words tagged STRIPPED. These are the ambiguous words, or words with duplicate meaning.
  • map the remaining arguments to regular double-dashed options using the DICTIONARY
  • words that are a direct match for a --option are automatically double-dashed
  • remaining words are left as is (these would be file names, key names, etc).
  • finally, the resulting "new" command line is parsed with regular options.
  • When arguments include "verbose", NLP system will print "before" and "after" of the arguments, so that any issues can be debugged and corrected.


and, a, the, it, item, to, key, with, about, for, of, new, make, store, in, print


                          clipboard   ───────➤   --copy
                             unlock   ───────➤   --decrypt
                               open   ───────➤   --edit
                               lock   ───────➤   --encrypt
                                      ───────➤   --backup
                                      ───────➤   --keychain
                               read   ───────➤   --file
                             create   ───────➤   --generate
                     ask enter type   ───────➤   --interactive
                               from   ───────➤   --keyfile
                         save write   ───────➤   --output
                      using private   ───────➤   --private_key
                              value   ───────➤   --string
       silently quietly silent shhh   ───────➤   --quiet
           secure secured protected   ───────➤   --password


# generate a new private key and copy to the clipboard but do not print to terminal
shhh create new key to clipboard quietly

# generate and save to a file a password-protected key, silently
shhh create a secure key and save it to "my.key"

# encrypt a plain text string with a key, and save the output to a file
shhh encrypt string "secret string" using $(cat my.key) save to file.enc

# decrypt a previously encrypted string:
shhh decrypt string $ENC using $(cat my.key)

# encrypt "file.txt" with key from my.key and save it to file.enc
shhh encrypt file file.txt with key from my.key and save it to file.enc

# decrypt an encrypted file and print it to STDOUT:
shhh decrypt file file.enc with key from "my.key"

# edit an encrypted file in $EDITOR, ask for key, and create a backup upon save
shhh edit file file.enc ask for a key and make a backup

# generate a new password-encrypted key, save it to your Keychain:
shhh create a new protected key store in keychain "my-keychain-key"

# print the key stored in the keychain item "my-keychain-key"
shhh print keychain "my-keychain-key"

# use the new key to encrypt a file:
shhh encrypt with keychain "my-keychain-key" file "password.txt" and write to "passwords.enc"

Ruby API

To use this library you must include the main Shhh module into your library.

Any class including Shhh will be decorated with new class methods #private_key and #create_private_key, as well as instance methods #encr, and #decr.

#create_private_key will generate a new key each time it's called, while #private_key will either assign an existing key (if a value is passed), or generate and save a new key in the class instance variable. Therefore each class including Shhh will use it's own key (unless the key is assigned).

The following example illustrates this point:

require 'shhh'

class TestClass
  include Shhh
@key = TestClass.create_private_key
@key.eql?(TestClass.private_key)  # => false
# A new key was created and saved in #private_key accessor.

class SomeClass
  include Shhh
  private_key TestClass.private_key

@key.eql?(SomeClass.private_key)  # => true (it was assigned)

Encryption and Decryption

So how would we use this library from another ruby project to encrypt and decrypt values?

After including the Shhh module in a ruby class, the class will now have the #encr and #decr instance methods, as well as #secret and `#create_private_key class methods.

Therefore you could write something like this below, protecting a sensitive string using a class-level secret.

require 'shhh'
class TestClass
  include Shhh
  private_key ENV['SECRET']

  def sensitive_value=(value)
    @sensitive_value = encr(value, self.class.private_key)
  def sensitive_value
    decr(@sensitive_value, self.class.private_key)

Full Application API

Since the command line interface offers more than just encryption/decryption, it is available via Shhh::Application class.

The class is instantiated with a hash that would be otherwise generated by Slop.parse(argv) – ie, typical options.

Here is an example:

require 'shhh/application'

key  = true).execute 
# => returns a new private key


The library offers a typical Shhh::Configuration class which can be used to tweak some of the internals of the gem. This is really meant for a very advanced user who knows what she is doing. The following snippet is actually part of the Configuration class itself, but can be overridden by your code that uses and initializes this library. Configuration is a singleton, so changes to it will propagate to any subsequent calls to the gem.

require 'zlib'
Shhh::Configuration.configure do |config|
  config.password_cipher = 'AES-128-CBC'  #
  config.data_cipher = 'AES-256-CBC'
  config.private_key_cipher = config.data_cipher
  config.compression_enabled = true
  config.compression_level = Zlib::BEST_COMPRESSION

As you can see, it's possible to change the default cipher typem, although not all ciphers will be code-compatible with the current algorithm, and may require additional code changes.

Managing Keys

There is a separate discussion about ways to securely store private keys in


After checking out the repo, run bin/setup to install dependencies. Then, run rake spec to run the tests. You can also run bin/console for an interactive prompt that will allow you to experiment.

To install this gem onto your local machine, run bundle exec rake install. To release a new version, update the version number in version.rb, and then run bundle exec rake release, which will create a git tag for the version, push git commits and tags, and push the .gem file to


Bug reports and pull requests are welcome on GitHub at

Feature Ideas

Natural Language Based API

This is the proposed mini-idea/specification for an alternative CLI that is at a feature parity with the standard flag-based CLI.

shhh generate key to the clipboard and keychain
shhh encrypt file 'hello' using $key [to output.enc]
shhh edit 'passwords.enc' using $key
shhh decrypt /etc/secrets encrypted with $key save to ./secrets
shhh encrypt with keychain $item file $input


The gem is available as open source under the terms of the MIT License.


This library is the work of Konstantin Gredeskoul, © 2016, distributed under the MIT license.