---
created_at: '2015-01-09T21:14:13.000Z'
title: Typing the Letters A-E-S Into Your Code (2009)
url: http://chargen.matasano.com/chargen/2009/7/22/if-youre-typing-the-letters-a-e-s-into-your-code-youre-doing.html
author: zorked
points: 168
story_text: ''
comment_text: 
num_comments: 63
story_id: 
story_title: 
story_url: 
parent_id: 
created_at_i: 1420838053
_tags:
- story
- author_zorked
- story_8864555
objectID: '8864555'

---
# If You’re Typing the Letters A-E-S Into Your Code You’re Doing It Wrong

## 1\. INT. COFFEE SHOP, MORNING

**DISCUSSING AN INTERVIEW**

A “young, cool-people’s” coffee shop on the first floor of an old office
building in downtown Chicago. “My band is playing” notices line the
wall. A hipster in a tight t-shirt hands a cappucino to MIKE TRACY while
THOMAS PTACEK waits impatiently. The coffee shop is loud; Mike and
Thomas raise their voices to be heard over the noise.

**MIKE TRACY**

Did you see that? He worked so hard on my coffee.

**THOMAS PTACEK**

What? Right. Whatever. Let’s get…

**MIKE TRACY**

He got all those little beans and put them in the thing and tamped them
down and

**THOMAS PTACEK**

Whatever. Ok. We’ve gotta get ready for this interview

**MIKE TRACY (CONT’D)**

and he clickity-clack clickity-clacked with the machine and

**THOMAS PTACEK**

Mike\! I get it\! He made the shit out of your coffee. What are we going
to ask this guy?

Mike walks to a table at the side of the shop, grabbing a lid and a
sleeve for his coffee.

**MIKE TRACY**

Miffed

I don’t know. It’s your interview. Single signon cookies?

**THOMAS PTACEK**

Why SSO?

Mike is maneuvering around people entering the shop through a door
leading out to the hallway.

**MIKE TRACY**

It’s got crypto in it. Everyone always fucks it up.

### INT. HALLWAY - CONTINUOUS

Thomas follows Mike, walking towards the elevators.

**THOMAS PTACEK**

Yeah, that could work. We’ll have two apps. User logged into one of
them, needs the other app to do something without making them log in.

**MIKE TRACY**

Print an invoice.

**THOMAS PTACEK**

Yeah, this will work. We’ll see if he comes up with the industry
standard answer; the cookie both apps honor to let you in, encrypted so
users can’t change their account to someone else’s.

**MIKE TRACY**

So, a base64 blob AES encrypted with a key both servers share? That’s
pretty easy, isn’t it? Are we sure this isn’t a layup?

DING. An elevator opens. Thomas and Mike step inside.

**THOMAS PTACEK**

You’ll be surprised.

## 2\. INT. OFFICE - LATER THAT MORNING

An unadorned off-white office lined with Ikea desks, piled with books,
papers, and in one case a pile of random electronics tools (soldering
iron, multi, etc). An EASEL PAD stands next to a large window looking
out on a brick wall. Thomas and Mike sit office chairs with THE
CANDIDATE.

**THOMAS PTACEK**

So you’d have app ‘A’ set a cookie with your account ID in it, right,
but how would you keep the user from switching their account by messing
with the cookie?

**THE CANDIDATE**

Uh, I’d encrypt the cookie?

**THOMAS PTACEK**

Show us how on the pad? \* Thomas hands THE CANDIDATE a dry erase
marker, as THE CANDIDATE walks to the easel pad.\*

**THE CANDIDATE**

Does it matter what language I write it in?

**MIKE TRACY**

Whatever you’re comfortable with.

**THE CANDIDATE**

Writing awkwardly, addressing the easel

Ok, so in C\#, I’d use `Response.Cookies`, and

**THOMAS PTACEK**

You can just do the part where you encrypt the cookies.

**THE CANDIDATE**

Oh, ok.

THE CANDIDATE writes on the pad, slowly

``` line-numbers
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
```

    public static string Encrypt(string toEncrypt, string key, bool useHashing)
    {
    
        byte[] keyArray = UTF8Encoding.UTF8.GetBytes(key);
        byte[] toEncryptArray = UTF8Encoding.UTF8.GetBytes(toEncrypt);
    
        if (useHashing)
            keyArray = new MD5CryptoServiceProvider().ComputeHash(keyArray);
    
        var tdes = new TripleDESCryptoServiceProvider()
            { Key = keyArray, Mode = CipherMode.ECB, Padding = PaddingMode.PKCS7 };
    
        ICryptoTransform cTransform = tdes.CreateEncryptor();
        byte[] resultArray = cTransform.TransformFinalBlock(
            toEncryptArray, 0, toEncryptArray.Length);
    
        return Convert.ToBase64String(resultArray, 0, resultArray.Length);
    }

**THE CANDIDATE**

Sorry.

**MIKE TRACY**

No worries, writing code during interviews sucks.

**THOMAS PTACEK**

Can you walk us through what that code is doing?

**THE CANDIDATE**

Sure. So I’m Triple-DES encrypting the cookie, which is
the `toEncrypt` function argument.

**MIKE TRACY**

Triple DES? Seriously?

**THE CANDIDATE**

Ah, yeah, you’re right, in my last job we had to use Triple DES for
campatibility, but I’d use AES now.

THE CANDIDATE starts correcting the text on the pad.

**THOMAS PTACEK**

Don’t worry about it, keep going. But yeah, don’t use Triple DES for
anything. It has a bunch of problems, but also an 8 byte block size,
which is tiny.

**THE CANDIDATE**

Ok, so, I take the key and I turn it into an AES key by MD5’ing it.

**MIKE TRACY**

You know MD5 is broken, right?

**THOMAS PTACEK**

Yeah, that’s not really the problem there though.

**THE CANDIDATE**

Oh, I could just use SHA-1.

**THOMAS PTACEK**

SHA-1 is really fast. Can you see why that’s a problem here?

**THE CANDIDATE**

Haltingly

Um. Not really? Don’t I want this to be fast?

**MIKE TRACY**

What’s in the cookie you’re encrypting again?

**THE CANDIDATE**

A string of URL arguments…

THE CANDIDATE starts writing on the
pad `userId=39493&role=user×tamp=1414919`

**MIKE TRACY**

So what’s to stop me from just running a dictionary through MD5,
generating a key, and trying to decrypt the cookie? I’ll know I won when
I get clean ASCII.

**THE CANDIDATE**

And how do I keep that from happening? You should use strong passwords
anyways. And I use a salt with the key anyways.

Mike vomits onto the floor.

**THOMAS PTACEK**

Gross.

**MIKE TRACY**

Wiping mouth

A salt doesn’t do anything here\!

**THOMAS PTACEK**

Just put a `for` loop around SHA-1 and run it 1000 times to generate the
key; that’ll at least slow down a brute force attack. SHA-1 is lightning
fast. By itself, it’s a crappy way to generate a key.

To Mike

Clean that up?

**THE CANDIDATE**

Well, I guess. Wait, why should we use a password here at all? I could
just use a random string of bytes…

THE CANDIDATE writes again on the whiteboard

``` line-numbers
1
```

    new RNGCryptoServiceProvider().GetBytes(keyArray);

**THOMAS PTACEK**

That is much better. Sometimes it’s a lot more convenient to use a
readable string. If you do, the loop around SHA-1 is similar to what
PBKDF does, which is I guess a best practice here. But if you can keep
structure out of your crypto keys, that’s much better.

**THE CANDIDATE**

Ok. Should I keep going?

**THOMAS PTACEK**

Your encryption function. Do you know what the `ECB` thing there means?

**THE CANDIDATE**

Oh, fuck\! You’re right, that should be `CBC`.

Pausing

Sorry for swearing.

**MIKE TRACY**

S’okay. You’ll fit right in.

**THOMAS PTACEK**

You know the difference between `ECB` and `CBC`?

**THE CANDIDATE**

Yeah, like, each block feeds into the next one?

THE CANDIDATE draws on the easel

![](/globalassets/newsroom/us/blog/images/2009/07/cbc1.png)

**THOMAS PTACEK**

Why’s that a win?

**THE CANDIDATE**

Because if any of the blocks repeat, you can see them repeat?

Mike has opened his laptop and is typing.

**MIKE TRACY**

To the laptop

We have a picture of that somewhere. Oh, here.

Mike raises the laptop up to show THE CANDIDATE

![](/globalassets/newsroom/us/blog/images/2009/07/ecb.jpg)

**MIKE TRACY (CONT’D)**

The top part is unencrypted. The bottom part is encrypted ECB. You’re
like Jack from Heat Vision and Jack.

**THE CANDIDATE**

I know EVERYTHING\! Right, because one bunch of 16 “black” bytes is the
same as the next, so they show up the same in the picture. Neat. Also,
in ECB mode you can cut and paste the blocks, right? He could take
the `userid`out of your cookie and put it in his own?

**THOMAS PTACEK**

Sure. That’s a good answer. Let’s move on. Say you’re implementing a web
server. What do you think, processes or threads?

## 3\. INT. OFFICE CONFERENCE ROOM - AFTERNOON

A room in the same office, roughly the same size, with an oversized
brown kitchen table in the middle, littered with paper and McDonalds
wrappers. Thomas and Mike sit at the table, talking to a CONFERENCE
PHONE.

**CONFERENCE PHONE**

So how’d he do?

**THOMAS PTACEK**

Pretty much aced it.

**MIKE TRACY**

What? He bombed the cookie part. He used ECB, MD5, and Triple DES\!

**THOMAS PTACEK**

I’m impressed that he could spell ECB, MD5, or Triple DES. And it
wouldn’t have mattered if he had used CBC, SHA-256, and AES-256. His
code still would have been broken.

**CONFERENCE PHONE**

How so?

**THOMAS PTACEK**

He didn’t authenticate the message. Encryption isn’t —

**MIKE TRACY**

Chanting

Encryption - isn’t - authentication.

**CONFERENCE PHONE**

Don’t you mean integrity?

**THOMAS PTACEK**

No, Dave, I mean authentication. They’re called message authentication
codes.

**CONFERENCE PHONE**

Ok, Tom. But he screwed that up?

**THOMAS PTACEK**

Yeah, but who cares? I’m surprised he even knew what CBC was. But we
just asked that to see how he thinks. We’re never going to let him
implement crypto code anyways.

**CONFERENCE PHONE**

I guess we don’t even let you write crypto code.

**THOMAS PTACEK**

Sure, and when I asked him about processes and threads…

**MIKE TRACY**

Can I stop you both here for a second?

**THOMAS PTACEK**

Yeah?

**MIKE TRACY**

This room is pretty fucking boring. We’re in a screenplay, right?

**THOMAS PTACEK**

Oh, yeah, you’re right. Let’s fix that.

Shouting

**Wings of silver\!**

**CONFERENCE PHONE**

**Nerves of steel\!**

**MIKE TRACY**

**Thundercats go\!**

### EXT. HURTLING THROUGH SPACE - CONTINUOUS

The office melts away around them, revealing a starfield hurtling past
as if moving at awesome speed. Meanwhile, the CONFERENCE PHONE
transforms into a UNICORN WITH LASER HORN.

**DAVE THE LASER UNICORN**

It’s “Silverhawks”, jackass.

**THOMAS PTACEK**

Where were we?

**MIKE TRACY**

Authentication?

**THOMAS PTACEK**

Oh yeah. Even if he had done AES-256-CBC. His code is still busted. I
can make his messages say whatever I want them to.

**DAVE THE LASER UNICORN**

How do you do that? Isn’t that the point of CBC mode? Anything you
change in the ciphertext randomizes the output. What can an attacker do
with that?

**THOMAS PTACEK**

First of all, sometimes randomizing the output is all you need. If one
of the key-value pairs in the cookie is your role, and the default role
is `admin`, but the server always generates a `role=user` field…

**MIKE TRACY**

Yikes. Yeah, that’s bad. Have you ever seen that bug in the wild?

**THOMAS PTACEK**

Garbling a block to confuse an app? I found a similar problem recently.
Login generates an encrypted cookie. Inside the cookie, comma-seperated
key-value pairs. If you put a comma in your user name, the server
doesn’t want you to inject your own key-value pairs, like “bob comma
admin equals yes”. So it quotes the commas. You can mess up a block to
eat the quote character.

**DAVE THE LASER UNICORN**

How do you know what block to mess up?

**THOMAS PTACEK**

It’s a cookie. You get unlimited tries. Each time, you add another ‘A’
to the login name, or mess with a different block. Eventually you line
things up just right so that you’ve garbled the quote character but not
the comma. Here, let me show you.

Thomas puts his hand to his forehead, and a beam of light emerges from
his forehead, projecting a picture, because it’s my script dammit.

![](/globalassets/newsroom/us/blog/images/2009/07/cbc2.png)

**THOMAS PTACEK**

Top hexdump. The plaintext of the cookie. Nothing’s been done to it.
Second hexdump. The encrypted cookie. Key doesn’t matter. Third hexdump.
I’ve flipped a bit in the second AES block.

**DAVE THE LASER UNICORN**

Convenient how AES blocks and hexdump lines are the same width.

**THOMAS PTACEK**

Fourth hexdump. The decrypted output, after flipping that bit in the
ciphertext. Notice that flipping one bit totally garbled the second
block — and ate my quote character.

**MIKE TRACY**

Doesn’t the app reject the cookie because of the garbled stuff in the
middle of it?

**THOMAS PTACEK**

Probably not. Why would it? C\# and Java and Ruby and Python don’t care
what go in your strings. And hey, if it does reject them, flip a
different bit. Totally different output. You get 2128 tries.

**MIKE TRACY**

Good point. What’s with the red “B” in the decrypted hexdump?

**THOMAS PTACEK**

Getting to that. Turns out, I can make the cookie say whatever I want.
It’s a property of CBC.

The property is this: take a ciphertext block and flip bit 0 (or 2, or
N). The resulting plaintext for that block? Garbage. But the next block
is normal… except has that bit flipped. Not good\!

**MIKE TRACY**

So you sacrifice one block and flip bits in the second block?

**THOMAS PTACEK**

Yeah. Although let’s stop calling it “flipping bits” and call it
“rewriting”, because that’s what you’re doing.

**DAVE THE LASER UNICORN**

If you know what bits to flip.

**THOMAS PTACEK**

You always know what the bits are.

**DAVE THE LASER UNICORN**

How?

**THOMAS PTACEK**

Because the bits are always 0x41414141.

**DAVE THE LASER UNICORN**

Huh?

**MIKE TRACY**

Because that’s what he stuffed them with. He logged in as bob
A-A-A-A-A-A-A-A-A.

**THOMAS PTACEK**

Right. An SSO cookie is usually, what, 100 bytes? If I stuff 1000 A’s
after my login name, and the cookie grows to 1100 bytes? Almost all of
those bytes are known to me. Here.

Again with the forehead beam thing.

![](/globalassets/newsroom/us/blog/images/2009/07/cbc3.png)

AES encrypt something that I partially control. Doesn’t matter what the
key is. Now XOR that block into the ciphertext. Decrypt it, and
somewhere in it you get a random block and `&admin=yes&x=AAAAA`.

**MIKE TRACY**

Not good.

**THOMAS PTACEK**

If you’re encrypting something it’s usually somehow user-controlled.
I’ll find that by plugging 100 A’s into each form field and waiting
for the cookie to grow.

**DAVE THE LASER UNICORN**

How will you know if the cookie is AES?

**THOMAS PTACEK**

Same way Chris Eng said to. Add A’s one at a time, see what increments
the cookie grows in. 16 bytes at a time? AES.

**DAVE THE LASER UNICORN**

And CBC?

**MIKE TRACY**

If you’re encrypting all A’s, the ciphertext blocks will repeat.

**DAVE THE LASER UNICORN**

And how do you know the format to write into the cookie?

**MIKE TRACY**

Who cares? Trial and error.

**THOMAS PTACEK**

Yeah. Point is, you thought encryption protected the contents of the
cookie. It doesn’t. Oh look, we’re almost there.

Thomas, Mike, and Dave hurtle towards a star system, a solar system, a
planet, powers-of-ten-style, towards the Michigan shore, converging
eventually on an office building, and then…

### INT. OFFICE CONFERENCE ROOM - AFTERNOON

**CONFERENCE PHONE**

That was really fucking anticlimactic.

### EXT. PARKING GARAGE - EARLY EVENING

Thomas stands next to his car, a black Volvo 850 held together with duct
tape, talking on a cell phone to NATE LAWSON.

**NATE LAWSON**

You know this scene is a really bad setup for a movie, right?

**THOMAS PTACEK**

Yeah yeah, whatever. Shut up before I turn you into a claymation
character. So yeah, it’s amazing how you can be a top tier vuln
researcher for over a decade and not really get how bad it is not to
have a MAC.

**NATE LAWSON**

A MAC doesn’t necessarily save you either.

**THOMAS PTACEK**

How so?

**NATE LAWSON**

There’s still a bunch of things you can do wrong. Like I was just
saying, Google Keyczar did almost everything right, but compared the MAC
using a timeable comparison function. You could tell how many bytes of
the MAC matched by watching how long the function took. People make that
mistake all the time. An even more common mistake is to generate an
error message when your padding is wrong. If you do that, you can
decrypt messages.

**THOMAS PTACEK**

I’ve heard about that. The Bleichenbacher PKCS thing, and the Vaudenay
paper.

**NATE LAWSON**

This was a major TLS finding too.

**THOMAS PTACEK**

I’ve never really been all that clear on how this works.

**NATE LAWSON**

Well you know how PKCS 7 padding works, right?

**THOMAS PTACEK**

Yeah, you have 2 bytes, you need to fill 16 bytes for an AES block, so
you fill the remaining 14 bytes with 0xe.

**NATE LAWSON**

So if you tack a random block onto a CBC message, what happens when the
receiver decrypts it?

**THOMAS PTACEK**

It comes out random.

**NATE LAWSON**

And the padding?

**THOMAS PTACEK**

Broken.

**NATE LAWSON**

Right. And if you send an error when that happens, you know the padding
failed. Now if you keep trying different random blocks, what’s
eventually going to happen?

**THOMAS PTACEK**

Uh…

**NATE LAWSON**

You’ll get a message with valid padding. Valid padding might be 0x3 0x3
0x3. Or it might be 0x4 0x4 0x4 0x4. But if you’re basically generating
random blocks, what’s the mostly likely padding you’re going to get that
will pass the check?

**THOMAS PTACEK**

0x1.

**NATE LAWSON**

Right. And you’re randomizing the output by tacking a random block in
front of real ciphertext, which gets XOR’d during decryption. So you
know the last byte of your random block…

**THOMAS PTACEK**

And the 0x1 that you know the padding is, and so that random byte XOR
the last byte of the plaintext is 0x1, and so you know the last byte of
the plaintext.

Pausing

And now that you know the last byte of the plaintext, you can make the
padding come out to 0x2 and try randomizing the other 15 bytes to find
out the next byte, and so on?

**NATE LAWSON**

Close enough.

**THOMAS PTACEK**

That is fucked up. All you did wrong was show me the exception your
library generated when you decrypted the block, and I could decrypt a
block. You got to reason byte by byte instead of block by block.

**NATE LAWSON**

You can decrypt whole messages that way. It’s called an error oracle.
You can’t show clients discernable errors. You can’t even take different
amounts of time to do things\! You can watch the system with random
inputs and measure how much time things take.

**THOMAS PTACEK**

There’s no way any programmer is ever going to get this stuff right.

**NATE LAWSON**

Professional crypto people don’t even get this stuff right. But if you
have to encrypt something, you might as well use something that has
already been tested.

**THOMAS PTACEK**

GPG for data at rest. TLS for data in motion.

**NATE LAWSON**

You can also use Guttman’s cryptlib, which has a sane API. Or Google
Keyczar. They both have really simple interfaces, and they try to make
it hard to do the wrong thing. What we need are fewer libraries with
higher level interfaces. But we also need more testing for those
libraries.

**THOMAS PTACEK**

Like I’ve been saying, if you have to type the letters “A-E-S” into your
source code, you’re doing it wrong.

**NATE LAWSON**

Uh. Ok. Whatever you say, Tom.

## 5\. FADE TO BLACK

Fade in epilogue

The next day, Thomas’ planet was destroyed. Have you guessed the name of
his planet? It was EARTH\! DON’T DATE ROBOTS.

**Published date:**\&nbsp 22 July 2009

**Written by:**\&nbsp Thomas Ptacek
