# Sym — Light Weight Symmetric Encryption for Humans
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**March 10th, 2017**: Please read the blog post [Dead Simple Encryption with Sym](http://kig.re/2017/03/10/dead-simple-encryption-with-sym.html) launching this tool and a library. Please leave comments or questions in the discussion thread at the bottom of that post. Thanks!
## Description
sym is a command line utility and a Ruby API that makes it trivial to encrypt and decrypt sensitive data. Unlike many other existing encryption tools, sym focuses on usability and streamlined interface (CLI), with the goal of making encryption easy and transparent. The result? There is no longer any excuse for keeping your application secrets unencrypted or outside of your repo.
sym uses symmetric Encryption which simply means that you will be using the same 256-bit key to encrypt and decrypt data. In addition to the private key, the encryption uses an IV vector. The library completely hides `iv` generation from the user, and automatically generates a random `iv` per encryption. Finally, each key can be uniquely password-protected (encrypted) and stored in OS-X Keychain, environment variable or a file.
### Motivation
The main goal when writing this tool was to streamline and simplify handling of sensitive data in a trasparent and easy to use way without sacrificing security.
Most common use-cases include:
* __Encrypting/decrypting of application secrets__, so that the encrypted secrets can be safely checked into the git repository and distributed, and yet without much of the added headache that this often requires
* __Secure message transfer between any number of receipients__
* __General purpose encryption/decryption with a single encryption key__, optionally itself re-encrypted with a password.
__Sym__ is a layer built on top of the [`OpenSSL`](https://www.openssl.org/) library, and, hopefully, makes encryption more accessible to every-day developers, QA, and dev-ops folks, engaged in deploying applications.
### What's Included
This gem includes two primary components:
1. [Rich command line interface CLI](#cli) with many features to streamline encryption/decryption.
2. Ruby API:
* [Basic Encryption/Decryption API](#rubyapi) is activated by including `Sym` module in a class, it adds easy to use `encr`/`decr` methods.
* [Application API](#rubyapi-app) is activated by instantiating `Sym::Application`, and using the instance to drive sym's complete set of functionality, as if it was invoked from the CLI.
* [Sym::MagicFile API](#magic-file) is a convenience class allowing you to read encrypted files in your ruby code with a couple of lines of code.
* [Sym::Configuration](#rubyapi-config) class for overriding default cipher, and many other parameters such as compression, cache location, zlib compression, and more.
### Massive Time Savers
What are the time savers that we mentioned earlier?
* By using Mac OS-X Keychain, `sym` offers a simple yet secure way of storing the key on a local machine, much more secure then storing it on a file system.
* By using a password cache (`-c`) via an in-memory provider such as `memcached` or `drb`, `sym` invocations take advantage of password cache, and only ask for a password once per a configurable time period.
* By using `SYM_ARGS` environment variable, where common flags can be saved.
* By reading a key from the default key source file `~/.sym.key` which requires no flags at all.
* By utilizing the `--negate` option to quickly encrypt a regular file, or decrypt an encrypted file with extension `.enc`.
* By using the `-t` (edit) mode, that opens an encrypted file in your `$EDITOR`, and replaces the encrypted version upon save & exit.
As you can see, we really tried to build a tool that provides good security for application secrets, including password-based encryption, but does not annoyingly ask for password every time. With `--edit` option, and `--negate` options you can treat encrypted files like regular files.
> Encrypting application secrets had never been easier! –– Socrates [LOL, -ed.]
## Using Sym
#### Installation
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 'sym'
And then run `bundle`.
Or install it into the global namespace with `gem install` command:
$ gem install sym
$ sym -h
$ sym -E # see examples
__BASH Completion__
Optionally, after gem installation, you can also install bash-completion of gem's command line options, but running the following command (and feel free to use any of the "dot" files you prefer):
sym -B ~/.bashrc
Should you choose to install it (this part is optional), you will be able to use "tab-tab" after typing `sym`, and you'll be able to choose from all of the supported flags.
#### Typical Use-Case Scenario
1. You generate a new encryption key, that will be used to both encrypt and decrypt the data. The key is 256 bits, or 32 bytes, or 45 bytes when base64-encoded, and can be generated with `sym -g`. The key must be saved somewhere for later retrieval. The key should not be easily accessible to an attacker. Note, that while generating the key, you can:
* optionally password protect the key with `sym -gp`
* save the key into a file with `sym -gpo key-file`
* save it into the OS-X Keychain, with `sym -gpx keychain-name`
* cache the password, with `sym -gpcx keychain-name`
* Normally, `sym` will print the resulting key to STDOUT
* You can prevent the key from being printed to STDOUT with `-q/--quiet`.
2. Next, let's assume you have a file or a string that you want to encrypt. We call this *data*.
3. In order to encrypt the __data__, we must supply an encryption key. Flag `-k` automatically retrieves the key, by trying to read it in several distinct ways, such as:
* a file with a pathname specified by the argument (eg, `-k ~/.key`)
* or environment variable (eg `-k ENC_KEY`)
* or OS-X Keychain entry
* verbatum string argument (not recommended)
* alternatively, you can paste the key interactively with `-i` or save the default key in `~/.sym.key` file.
4. Finally, we are ready to encrypt. The data to be encrypted can be read from a file with `-f filename`, or it can be read from STDIN, or a passed on the command line with `-s string`. For example, `sym -e -k ~/.key -f /etc/passwd` will encrypt the file and print the encrypted contents to STDOUT.
4. Instead of printing to STDOUT, the output can be saved to a file with `-o ` or a simple redirect or a pipe.
5. Encrypted file can later be decrypted with `sym -d ...` assuming the same key it was encrypted with.
6. Encrypted file with extension `.enc` can be automatically decrypted with `-n/--negate` option; if the file does not end with `.enc`, it is encrypted and `.enc` extension added to the resulting file.
7. With `-t` flag you can open in VIM (or `$EDITOR`) any encrypted file and edit it. Once you save it, the file gets re-encrypted and replaces the previous version. A backup can be created with `-b` option. See the section on [inline editing](#inline)
A sample session that uses Mac OS-X Keychain to store the password-protected key.
```bash
# Gen a new key, password-encrypt it, cache the password, save
# result in the key chain entry 'my-new-key' (but don't print it '-q')
❯ sym -gpqcx my-new-key
New Password : •••••••••
Confirm Password : •••••••••
❯ sym -eck my-new-key -s 'My secret data' -o secret.enc
Password: •••••••••
❯ cat secret.enc
BAhTOh1TeW06OkRhdGE6OldyYXBFefDFFD.....
❯ sym -dck my-new-key -f secret.enc
My secret data
# Now, let's save our keychain key in the default key file:
❯ sym -ck my-new-key -o ~/.sym.key
# Now we can decrypt/encrypt with this key at will
❯ sym -n secret.enc
# created a decrypted file `secret`
# Lets now save common flags in the SYM_ARGS bash variable:
❯ export SYM_ARGS="-ck my-new-key"
❯ sym -df secret.enc
My secret data
```
Note that password caching is off by default, but is enabled with `-c` flag. In the example above, the decryption step fetched the password from the cache, and so the user was not required to re-enter the password.
#### Inline Editing of Encrypted Files
The `sym` CLI tool supports one particularly interesting mode, that streamlines handling of encrypted files. The mode is called __edit mode__, and is activated with the `-t` flag.
Instead of decrypting data anytime you need to change it into a new file and then manually re-encrypting the result, you can use the shortcut flag `-t` (for "edi**t**"), which decrypts your data into a temporary file, automatically opening it with an `$EDITOR`.
sym -t -f config/application/secrets.yml.enc -k ~/.key
> This is one of those time-saving features that can make a difference in making encryption feel easy and transparent.
> NOTE: this mode does not seem to work with GUI editors such as Atom or TextMate. Since `sym` waits for the editor process to complete, GUI editors "complete" immediately upon starting a windowed application.
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`)".
Example: here we edit an encrypted file in `vim`, while using interactive mode to paste the key (`-i | --interactive`), and then creating a backup file (`-b | --backup`) upon save:
sym -tibf data.enc
# => Private Key: ••••••••••••••••••••••••••••••••••••••••••••
#
# => Diff:
# 3c3
# # (c) 2015 Konstantin Gredeskoul. All rights reserved.
# ---
# # (c) 2016 Konstantin Gredeskoul. All rights reserved.
Note the `diff` shown after save.
## Ruby API
### Including `Sym` module
Low-level encryption routines can be imported by including `Sym` module into your class or a module. Such class will be decorated with new class methods `#private_key` and `#create_private_key`, as well as instance methods `#encr`, and `#decr`.
#### Class Method `#create_private_key()`
This method will generate a new key each time it's called.
#### Class Method `#private_key(value = nil)`
This method 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 `Sym` will (by default) use a unique key (unless the key is passed in as an argument).
The following example illustrates this point:
```ruby
require 'sym'
class TestClass
include Sym
end
@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 Sym
private_key TestClass.private_key
end
@key.eql?(SomeClass.private_key) # => true (it was assigned)
```
#### Encrypting and Decrypting
So how would we use this library from another Ruby project to encrypt and decrypt values?
After including the `Sym` module, two instance methods are added:
* `#encr(value, private_key)` and
* `#decr(value, private_key)`.
Therefore you could write something like this below, protecting a sensitive string using a class-level secret.
```ruby
require 'sym'
class TestClass
include Sym
private_key ENV['SECRET']
def sensitive_value=(value)
@sensitive_value = encr(value, self.class.private_key)
end
def sensitive_value
decr(@sensitive_value, self.class.private_key)
end
end
```
#### Encrypting the Key Itself
You can encrypt the private key using a custom password. This is highly recommended, because without the password the key is the only piece that stands between an attacker and decrypting your sensitive data.
For this purpose, two more instance methods exist:
* `#encr_password(data, password, iv = nil)`
* `#decr_password(encrypted_data, password, iv = nil)`
They can be used independently of `encr` and `decr` to encrypt/decrypt any data with a password.
### Using `Sym::MagicFile` API for Reading/Writing Encrypted/Decrypted data
This is probably the easiest way to leverage Sym-encrypted files in your application — by loading them into memory with `Sym::MagicFile`. This class provides a very simple API while supporting all of the convenience features of the rich application API (see below).
You instantiate `Sym::MagicFile` with just two parameters: a `pathname` to a file (encrypted
or not), and the `key` identifier. The identifier can either be a filename, or
OS-X Keychain entry, or environment variable name, etc — basically it is resolve
like any other `-k ` CLI flag.
The following methods are available:
* `#encrypt` — returns an encrypted string representing the encrypted contents ofa file specified by the pathname.
* `#decrypt` — returns a decrypted string representing the decrypted contents of a file specified by the pathname.
* `#encrypt_to(filename)` — encrypts the contents of a file specified by the pathname, and writes the result to a `filename`.
* `#decrypt_to(filename)` — decrypts the contents of a file specified by the pathname, and writes the result to a `filename`.
#### Example: Using `Sym::MagicFile` with the `RailsConfig` (or `Settings`) gem
In this example, we assume that the environment variable `$PRIVATE_KEY` contain
the key to be used in decryption.
```ruby
require 'sym/magic_file'
require 'yaml'
secrets = Sym::MagicFile.new('/usr/local/etc/secrets.yml.enc', 'PRIVATE_KEY')
hash = YAML.load(secrets.decrypt)
```
Let's say that you are using [RailsConfig](https://github.com/railsconfig/config) gem for managing your Rails application setings. Since the gem allows appending settings from a hash, you can simply do the following in your `settings_initializer.rb`, and after all of the unencrypted settings are loaded:
```ruby
require 'config'
require 'sym/magic_file'
require 'yaml'
Settings.add_source!(
YAML.load(
Sym::MagicFile.new(
'/usr/local/etc/secrets.yml.enc',
'PRIVATE_KEY'
).decrypt)
)
Settings.reload!
```
### Using `Sym::Application` API
Since the command line interface offers much more than just encryption/decryption of data with a key, majority of these features are available through `Sym::Application` instance.
The class is instantiated with a hash that would be otherwise generated by parsing CLI arguments, typical `options`. For example, to generate the key, pass `generate: true` — essentially any flag in it's long form can be converted into a hash member.
Here is an example:
```ruby
require 'sym/application'
key = Sym::Application.new(generate: true).execute
# => '75ngenJpB6zL47/8Wo7Ne6JN1pnOsqNEcIqblItpfg4='
```
### Ruby API Conclusion
Using `Sym`'s rich ruby API you can perform both low-level encryption/decryption, as well as high-level management of encrypted files. By using `Sym::MagicFile` and/or `Sym::Application` classes you can access the entire set of functionality expressed vi the CLI, described in details below.
## Using `sym` with the Command Line
### Encryption Keys
The private key is the cornerstone of the symmetric encryption. Using `sym`, the key can be:
* generated and printed to STDOUT, or saved to Mac OS-X KeyChain or a file
* fetched from the Keychain in subsequent operations
* password-protected during generation (or import) with the `-p` flag.
* password can be cached using either `memcached` or `dRB` server, if the `-c` flag is provided.
* must be kept very well protected and secure from attackers.
The __unencrypted private__ key will be in the form of a base64-encoded string, 45 characters long.
__Encrypted (with password) private key__ will be considerably longer, perhaps 200-300 characters long.
#### Generating the Key — Examples
```bash
# Let's generate a new key, and copy it to the clipboard (using `pbcopy` command on Mac OS-X):
$ sym -g | pbcopy
# Or save a new key into a bash variable
$ KEY=$(sym -g)
# Or save it to a file:
$ sym -go ~/.key
# Or create a password-protected key (`-p`), and save it to a file (`-o`),
# cache the password (`-c`), and don't print the new key to STDOUT (`-q` for quiet)
$ sym -gpcqo ~/.secret
New Password: ••••••••••
Confirm Password: ••••••••••
$
```
#### Resolving the `-k` Argument
You can use the generated private key by passing an argument to the `-k` flag.
**Sym** attempts to automatically resolve the key source by trying each of the following options, and then moving on to the next until the key is found, or error is shown:
1. the `-k value` flag, where the *value* is one of:
* a file path, eg (`-k ~/.key`)
* an environment variable name (`-k MY_KEY`)
* an actual base64-encoded key (not recommended for security reasons)
* a keychain name (`-k keychain-entry-name`)
2. pasting or typing the key with the `-i` (interactive) flag
3. if exists, a default key file, located in your home folder: `~/.sym.key` is used only when no other key-specifying flags were passed in.
#### Encryption and Decryption
#### Inline Editing
The `sym` CLI tool supports one particularly interesting mode, that streamlines handling of encrypted files. The mode is called __edit mode__, and is activated with the `-t` flag.
In this mode `sym` can decrypt the file, and open the result in an `$EDITOR`. Once you make any changes, and save it (exiting the editor), `sym` will automatically diff the new and old content, and if different – will save encrypt it and overwrite the original file.
> NOTE: this mode does not seem to work with GUI editors such as Atom or TextMate. Since `sym` waits for the editor process to complete, GUI editors "complete" immediately upon starting a windowed application.
In this mode several flags are of importance:
-b (--backup) – will create a backup of the original file
-v (--verbose) - will show additional info about file sizes
Here is a full command that opens a file specified by `-f | --file`, using the key specified in `-k | --keyfile`, in the editor defined by the `$EDITOR` environment variable (or if not set – defaults to `/bin/vi`)".
To edit an encrypted file in `$EDITOR`, while asking to paste the key (`-i | --interactive`), while creating a backup file (`-b | --backup`):
sym -tibf data.enc
# => Private Key: ••••••••••••••••••••••••••••••••••••••••••••
#
# => Diff:
# 3c3
# # (c) 2015 Konstantin Gredeskoul. All rights reserved.
# ---
# # (c) 2016 Konstantin Gredeskoul. All rights reserved.
#### Using KeyChain Access on Mac OS-X
KeyChain storage is a huge time saver. It allows you to securely store the key the keychain, meaning the key can not be easily extracted by an attacker without a login to your account. Just having access to the disk is not enough.
Apple had 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 the iCloud you will have access to it on other machines
As mentioned previously, to add the key to the KeyChain on the Mac, use `-x ` flag with `-g` flag when generating a key. The `key name` is what you call this particular key, based on how you plan to use it. 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:
sym -gx staging # the key is passwordless
sym -gpcx staging # this key is password protected, with the password cached
Next, whenever you need to *use* this key, you can specify the key with `-k staging`.
Finally, you can delete a key from KeyChain access by running:
keychain delete
Below we describe the purpose of the executable `keychain` shipped with sym.
#### KeyChain Key Management
`keychain` is an additional executable installed with the gem, which can be used to read (find), update (add), and delete keychain entries used by `sym`.
It's help message is self-explanatory:
Usage: keychain [ add | find | delete ]
#### Moving a Key to the Keychain
You can easily move an existing key from a file or a string to a keychain by combining -k or -k to read the key, with -x to write it.
sym -k $keysource -x mykey
#### Adding Password to Existing Key
You can add a password to a key by combining one of the key description flags (-k, -i) and then also -p. Use `-q` to hide new key from the STDOUT, and `c` to cache the password.
sym -k $mykey -pqcx moo
The above example will take an unencrypted key passed in `$mykey`, ask for a password and save password protected key into the keychain with name "moo."
#### Password Caching
Nobody likes to re-type passwords over and over again, and for this reason *Sym* supports password caching via either a locally running `memcached` instance (the default, if available), or a locally started `dRB` (distributed Ruby) server based on the `Coin` gem.
Specifics of configuring both Cache Providers is left to the `Configuration` class, an example of which is shown below in the Ruby API section.
In order to control password caching, the following flags are available:
* `-c` turns on caching
* `-u seconds` sets the expiration for cached passwords
* `-r memcached | drb` controls which of the providers is used. Without this flag, *sym* auto-detects caching provider by first checking for `memcached`, and then starting the `dRB` server.
#### Saving Common Flags in an Environment Variable
You can optionally store frequently used flags for `sym` in the `SYM_ARGS` environment variable. For example, to always cache passwords, and to always use the same encryption key from the keychain named "production", set the following in your `~/.bashrc`:
```
export SYM_ARGS="-cx production"
```
This will be automatically appended to the command line if the `-A/--sym-args` flag is provided, and so to encrypt/decrypt anything with password caching enabled and using that particular key, you would simply type:
```bash
# -cx production are added from SYM_ARGS
sym -Aef file -o file.enc
# And to decrypt:
sym -Adf file.enc -o file.original
# Or edit the encrypted file:
sym -Atf file.enc
```
#### CLI Help Screen and Examples
This may be a good time to take a look at the full help message for the `sym` tool, shown naturally with a `-h` or `--help` option. Examples can be shown with `-E/--examples` flag.
Please take a look at the [SYM-CLI](SYM-CLI.md) for a complete help screen and the examples.
## Fine Tuning
### Configuration
The library contains a `Sym::Configuration` singleton class, which can be used to tweak some of the internals of the gem. Its meant for advanced users who know what they are doing. The code snippet shown below is an actual default configuration. You can override the defaults by including a similar snipped in your application initialization, right after the `require 'sym'`. The `Configuration` class is a Singleton, so changes to it will propagate to any subsequent calls to the gem.
```ruby
require 'zlib'
require 'sym'
Sym::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
config.encrypted_file_extension = 'enc'
config.default_key_file = "#{ENV['HOME']}/.sym.key"
config.password_cache_timeout = 300
# When nil is selected, providers are auto-detected.
config.password_cache_default_provider = nil
config.password_cache_arguments = {
# Ruby dRB-based in-memory cache.
drb: {
opts: {
uri: 'druby://127.0.0.1:24924'
}
},
# Memcached Provider – local is the default, but can be changed.
memcached: {
args: %w(127.0.0.1:11211),
opts: { namespace: 'sym',
compress: true,
expires_in: config.password_cache_timeout
}
}
}
end
```
As you can see, it's possible to change the default cipher type, although not all ciphers will be code-compatible with the current algorithm, and may require additional code changes.
#### Encryption Features & Cipher
The `sym` 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, that
* can be generated and is a *base64-encoded* string about 45 characters long. The *decoded* key is always 32 characters (or 256 bytes) long.
* can be optionally password-encrypted using the 128-bit key, and then be automatically detected (and password requested) when the key is used
* can optionally have its password cached for 15 minutes locally on the machine using `memcached` or using a `dRB` server
* 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.
## Development
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 [rubygems.org](https://rubygems.org).
#### Contributing
Bug reports and pull requests are welcome on GitHub at [https://github.com/kigster/sym](https://github.com/kigster/sym)
### License
`Sym` library is © 2016-2017 Konstantin Gredeskoul.
The gem is available as open source under the terms of the [MIT License](http://opensource.org/licenses/MIT).
The library is designed to be a layer on top of [`OpenSSL`](https://www.openssl.org/), distributed under the [Apache Style license](https://www.openssl.org/source/license.txt).
### Acknowledgements
While [Konstantin Gredeskoul](http:/kig.re) is the primary developer of this library, contributions are very much encouraged. Any pull requests will be reviewed promptly. Please submit feature requests, bugs, or a good word :)
#### Contributors:
* [Wissam Jarjoui](https://github.com/bosswissam)
* Megan Mathews
* Barry Anderson