A python's escape from PlaidCTF jail

Python jails are pretty common among CTF challenges. Often a good knowledge of the interpreter’s internals gets you a long way. For the non initiated it might sometimes seem like black magic. PlaidCTF offered a challenging task that required the combination of some different techniques and logic.

This time there was a service listening on the remote server, with a python script called for each new connection. We were told we had to get a shell because we couldn’t guess where the flag was stored. Another important detail is that the challenge was running on python2.6.6.

The script was given to us and you can find its code here.


Basically it sets up a jail, and then executes user input after some restricting checks. I shall present the different protections before explaining how we can bypass most of them, and finally escape from this jail.

from sys import modules
del modules

sys.modules is a dictionary that contains all the modules which where imported since the interpreter started. Clearing the modules breaks a lot of things. It breaks a lot of stuff because often a standard function will check if some module is present. But deleting the modules altogether breaks even more code, because now the check itself raises an exception!

The next step in setting up the jail’s environment is this:

__builtins__ = None

This is pretty self explanatory. It clears the dictionary python uses to find its builtins and we can’t use them anymore except if we already have a reference to the builtin we need somewhere else.

There is one protection left, but it doesn’t try to limit what we can do, it only tries to make it harder by filtering out certain characters and imposing a length limit. Notice that the script calls _raw_input, which is just backup it made of raw_input before clearing the builtins.

inp = _raw_input()
inp = inp.split()[0][:1900]
#Dick move: you also have to only use the characters that my solution did.
inp = inp.translate("".join(map(chr, xrange(256))),

Basically this means our input should be 1900 bytes or less, and should only contain characters in the set([':', '%', "'", '’, ‘(‘, ‘,’, ‘)’, ‘}’, ‘{‘, ‘[’, ‘.’, ‘]’, ‘<’, ‘_’, ‘~’])`, the split ensures there can’t be any white- spaces. It’s important to note that we are also allowed to use most of the non printable characters if we want to.

After all this we finally get to the interesting part: code execution! We are lucky because it is in two stages, so we have twice the fun :-)

exec 'a=' + _eval(inp, {}) in {}

Don’t be fooled. The eval is not in the exec. It could be written like this:

cmd = 'a=' + _eval(inp, {})
exec cmd in {}

Quick reminder, in python eval is used to evaluate an expression and returns its value whereas exec is a statement that compiles and executes a set of statements. In short this means you can execute statements when you are using exec but not when using eval.

The empty dict given to eval as its second parameter and the in {} after the exec both mean the same thing, that the code should be evaluated in a new empty scope. So we can’t (in theory) pass stuff from the eval to the exec, or interact with the outer-world in any way.

Most of python are just references, and this we can see here again. These protections only remove references. The original modules like os, and the builtins are not altered in any way. Our task is quiet clear, we need to find a reference to something useful and use it to find the flag on the file system. But first we need to find a way of executing code with this little characters allowed.

Running code

How do we get code running with only characters from set([':', '%', "'", '’, ‘(‘, ‘,’, ‘)’, ‘}’, ‘{‘, ‘[’, ‘.’, ‘]’, ‘<’, ‘_’, ‘~’])`? Answer: It’s python, python is fun, let’s have some fun.

We have everything we need to build tuples (), lists [] and dictionaries {:}. If it was python 2.7 we could also make sets using {} but sadly that isn’t the case. We can also build strings using ' ' and we could use % to do some formatting. The comma will obviously help when building tuples or lists, and the dot might be useful to access attributes.

We haven’t talked about <, ~, _ and `, yet. < and ~ are simple operators, we can do less-than comparison and binary-negation. _ would be a way to have something valid for a variable identifier, but we do not have = so that might not be of much use.

Now, if you are like me and didn’t know ` actually did something in python2 you might be surprised! As it turns out `x` is equivalent to repr(x)! This means we can produce strings out of objects.

Some of these symbols can be used for multiple purposes, % can be used for string formatting but also for integer modulo and < can be used both for comparing to integers and in the form of << binary-shifting them to the left

We can see that most of the characters we are allowed to use are pretty useful and I dare say it is easier doing python with only those than it would be without them!

Remember we have two execution stages, first the eval, then the exec. The exec executes what the eval returns. So we should consider the eval as a decoder. The 1900 character limit is supposed to force you to think a lot about this, but we bypassed it (as I will explain later), that is why we didn’t put to much thought into the encoding scheme.

The first thing to notice is that []<[] is False, which is pretty logical. What is less explainable but serves us well is the fact that {}<[] evaluates to True.

True and False, when used in arithmetic operations, behave like 1 and 0. This will be the building block of our decoder but we still need to find a way to actually produce arbitrary strings.

Getting characters

Let’s start with a generic solution, we will improve on it later. Getting the numeric ASCII values of our characters seems doable with True, False, ~ and <<. But we need something like str() or "%c". This is where the invisible characters come in handy! "\xcb" for example, it’s not even ascii as it is larger than 127, but it is valid in a python string, and we can send it to the server.

If we take its representation using `'_\xcb_'` (In practice we will send a byte with the value 0xcb not '\xcb'), we have a string containing a c. We also need a '%', and we need those two, and those two only.

We want this: `'%\xcb'`[1::3] , using True and False to build the numbers we get:


There you go! Now provided we can have any number build using the same trick as for the indexes we just have to use the above and %(number) to get any character we want.

Some optimization is possible for specific characters by finding them in the representations of True, False and the invisible characters. As I am about to bypass the length limit I didn’t bother doing this to much.


This is where I failed during the CTF and what cost me the shame of getting the flag five minutes after the end. Had I coded something to automate the process of getting arbitrary numbers I wouldn’t have missed spaces when I finally got a shell. But more on that later. The point is I shall do it right now.

If you have ever studied any logic you might have encountered the claim that everything could be done with NAND gates. NOT-AND. This is remarkably close to how we shall proceed, except for the fact we shall use multiply-by-two instead of AND. We won’t use True.

Everything can be done using only False (0), ~ (not), << (x2), let me show you with an example. We shall go from 42 to 0 using ~ and /2, then we can revert that process using ~ and *2.

 42 # /2
 21 # ~
-22 # /2
-11 # ~
 10 # /2
  5 # ~
 -6 # /2
 -3 # ~
  2 # /2

True = ~(~(~(~(42/2)/2)/2)/2)/2/2

Basically we divided by two when we could, else we inverted all the bits. The nice property of this is that when inverting we are guaranteed to be able to divide by two afterward. So that finally we shall hit 1, 0 or -1.

But wait. Didn’t I say we would not use True, 1? Yes I did, but I lied. We will use it because True is obviously shorter than ~(~False*2), especially considering the fact we will use True anyway to do x2, which in our case is of course <<({}<[]).

Anyway, the moment we hit 1, 0 or -1 we can just use True, False or ~False.

So now we can reverse this and we have:

42 = ~(~(~(~(1*2)*2)*2)*2)*2

Using what we are allowed to:

42 = ~(~(~(~(({}<[])<<({}<[]))<<({}<[]))<<({}<[]))<<({}<[]))<<({}<[])

How to not loose a CTF:

def brainfuckize(nb):
    if nb in [-2, -1, 0, 1]:
        return ["~({}<[])", "~([]<[])",
		         "([]<[])",  "({}<[])"][nb+2]

    if nb % 2:
        return "~%s" % brainfuckize(~nb)
        return "(%s<<({}<[]))" % brainfuckize(nb/2)

I wonder if using % as a modulo might optimize the length of some of these expressions. If you have any thoughts about this feel free to talk to me about it!

And in the darkness bind them!

Joining is not trivial, but there is a little trick that makes it quite easy. If we were building a list of characters the representation of that list would contain all those characters (obviously), and the best part is they should be equally spaced. A simple slice should be enough to give us the complete string.

>>> `['a', 'b', 'c', 'd']`[2::5]

>>> `['a', 'b', 'c', 'd']`[(({}<[])<<({}<[]))::~(~(({}<[])<<({}<[]))<<({}<[]))]

Since we have the ability to generate arbitrary numbers and single characters this works well.

However care must be taken because this does not always work. In particular when the representation of a character is composed of more than one character, such cases include but are not limited to \n, \t, \\, etc… Luckily those characters are seldom needed, and we won’t use them.

We can now generate almost all the code we want from the eval() and it will be passed to the exec statement!

Before moving on to the next step, let’s enjoy some valid python code!


About python scopes

At this stage, and before trying to exploit anything, I think it might be useful to give a quick aperçu of how python handles scopes. This won’t explain everything there is to know about it and I strongly suggest you should read more about it is your are interested. If, however, you feel perfectly comfortable with the way python handles and stores this stuff you may safely skip this section.

There are two kinds of variables that I will talk about, namely global and local variables. Of course, being python, there is no real difference between the way a variable referring to a number, a class or a function, is handled.


What we usually call global variables are not in fact global in the same sense as global variables in C would be. They are only global relative to the module in which they are defined. When accessing them from outside there module you would do for example: math.pi to access the global variable named 'pi' in the module 'math'.

All the global variables in a module are stored in the module’s __dict__ which is an attribute of the module. Modifing this __dict__ has the same effect as using setattr on the module.

One can get the current module’s globals doing sys.modules[__name__].__dict__, or more simply by calling globals().


Local variables are those defined inside the scope of a function. In a way similar to global variables, locals are stored in a dictionary that can be accessed through the f_locals attribute of the code frame in which the function is/was running. In the CPython implementation modifying the f_locals wont affect the actual locals.

from the outside

If we take a look at the code of math.cos we might expect it to use math.pi, but it will probably be simply referenced as pi. When we call math.cos from somewhere outside of math, pi wont be in the globals of the calling module. Its interesting to learn how cos finds the reference on pi. During the declaration of the function, a reference to the current globals (those of the module in which it is declared) is kept in the function’s func_globals attribute.


We are now able to run code quiet easily and the character problems are mostly solved. (We still can’t use some characters but we shall do without them) However, some limits still remain. No builtins, no access to modules, and a character limit. Let’s solve that last problem first, that way it won’t bother us afterwards.

Solving the length limit

To achieve this we shall add a third execution stage, the second stage (the original exec statement), which can be triggered as many times as we want, will be tasked with building the final payload. For this it will need to store the query parts somewhere, and concatenate the new parts as they arrive.

We need a place to store stuff where we can comeback in the next exec. Finding a place where we can comeback is easy.

If you have ever done any kind of python jail-escaping the following should be familiar to you.


This get’s the tuple’s type’s (().__class__) parent (__base__) which is object, then lists all its subclasses that python knows of. Somewhere in those we should be able to find one which we are allowed to call setattr on. Indeed we are lucky and find:

>>> ().__class__.__base__.__subclasses__()[-2]
<class 'codecs.IncrementalDecoder'>

>>> ().__class__.__base__.__subclasses__()[-2].test = "wapiflapi"
>>> print ().__class__.__base__.__subclasses__()[-2].test

All the code should work on python 2.6.6, but it is trivial to adapt to other versions.

Neat, we can store stuff in this and come back to it later. That’s all we need for our second stage, we are ready to receive the parts from eval, concatenate them into our storage and finally exec the whole payload when we are done.

Battle plan:

  • Stage 1, original eval()
    • Decode input and generate the python code
    • This bypasses the character limit
  • Stage 2, original exec
    • Concatenate stage 1’s output
    • exec when ready
    • This bypasses the length limit
  • Stage 3, exec by stage 2
    • Actual payload, will hopefully get us a shell
    • This gets out of jail

This basically solves the problem at hand (the length limit), the code is pretty trivial and will be shown later when putting everything together. Let’s first find-out how to really escape from jail.

Getting out

We want a shell, we want system, execv, fork, dup, in short we want the os module. Where can we find it? We need to look for a module or function that has a reference on os or on something that has a reference on something like that. Here experience plays a big role, and we know from experience that the warnings module is loaded by default and has a lot of nice references. If we can get its globals we should be fine.

What we normally try, and it worked for the NDH Prequals is :

>>> [x for x in ().__class__.__base__.__subclasses__() if x.__name__ == "catch_warnings"][0]()._module
<module 'warnings' from '/usr/lib/python2.7/warnings.pyc'>

This gives us the module straightaway, no questions asked. It’s so easy because catch_warnings keeps a reference to its module. But it didn’t work this time because catch_warnings uses sys.modules to get that reference, and thus it fails. (They are .clear()ed, remember?)

Traceback (most recent call last):
  File "/Python-2.6.6/Lib/warnings.py", line 333, in __init__
    self._module = sys.modules['warnings'] if module is None else module
KeyError: 'warnings'

But we still have a way of getting that reference, we saw that functions kept a reference to the globals of the modules in which they where defined. We only have to find a real function in catch_warnings and we should be good to go.

After some searching we find out catch_warnings.__repr__ is backed by a real function. __repr__ itself is an ‘instancemethod’ not a function, but it’s trivial to get the function using __repr__.im_func

Then it’s only a matter of getting warnings' globals using func_global which is a reference to it.

>>> g_warnings = [x for x in ().__class__.__base__.__subclasses__() if x.__name__ == "catch_warnings"][0].__repr__.im_func.func_globals
>>> print g_warnings["linecache"].os
<module 'os' from '/Python-2.6.6/Lib/os.pyc'>

warnings imports linecache which in turn imports os. We don’t import anything and that is why doing things like this doesn’t disturb the broken mess caused by sys.modules.clear().


Now we know everything. We know how to escape the jail, we know how to have enough space to do so and we know how to use the characters we want to craft our code. The only think we miss is putting all this together. And it’s pretty easy.

I’d like to thank PPP for their CTF, I really enjoyed it. Also thank you to all the people who helped me learning python and some of its secrets.