Authentication with Hash Chains in C

Datetime:2016-08-23 01:20:06         Topic:         Share        Original >>
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Stephen Brennan • 19 June 2016

One of my silliest long-running projects is a chatbot called cbot . All it does is connect to an IRC (Internet Relay Chat) server, and respond to people’s messages. For instance, if you greet it, it will greet you back. If you insult it, it will send you a poorly-constructed comeback. Obviously there’s nothing groundbreaking about it - there are other chatbots that are much better. I made cbot because I wanted to learn some new concepts (specifically the IRC protocol and dynamic loading), and it was really helpful for that purpose. Plus, it’s another project in C, and I like projects in C!

I’ve been tinkering with cbot lately, and I realized that I wanted to add some commands that only I can run. For instance, making it switch channels or leave IRC. Or even change its nickname. The problem was that I didn’t have a good way to authenticate myself. I can’t just whitelist my IRC nickname, because anyone can change their nickname - if I disconnected, someone could steal my nickname and control my bot. So I started brainstorming some more, uh, “elaborate” solutions to this problem.

Today I came up with a solution I think is pretty great: hash chains!

What’s a hash chain?

In computer science, we have a concept of a “cryptographic hash function”. They sound complicated (and they are), but their concepts are simple. The idea is that they should take some data as input and produce a big number—a “hash”—as output. The important thing is that it should be very difficult for somebody to figure out what the input data was for a given hash.

In a hash chain, you simply start with a number, and you hash it. Then, you hash the result. Then you hash that result. You end up getting a sequence of hash values like this:

seed = some number
hash_0 = H(seed)
hash_1 = H(hash_0)
hash_2 = H(hash_1)
hash_n = H(hash_n-1)

If someone were to give you hash_n-1 and hash_n , it would be easy for you to verify that they are part of the same hash chain. You’d just have to make sure that H(hash_n-1) was equal to hash_n . But if somebody gave you hash_n and nothing else, it would be impossible for you to figure out any of the previous hash values in this chain.

Hash chains for authentication

So how can we use this to authenticate my commands to cbot? It’s quite simple. First, we generate a big, long hash chain. Maybe 1000 hashes in the chain. We keep the seed of that chain a secret. Or, we randomly generate it and forget about it. It doesn’t matter too much.

What does matter is that we keep a copy of the whole hash chain somewhere safe.

Then, we give cbot a single hash value: hash_1000 in this case. Cbot hangs onto this in memory, and whenever I want to give it a command, I give it hash_999 as “proof” of my identity. To verify it, cbot does two things:

  1. Verify that H(hash_999) equals hash_1000 .
  2. Replace hash_1000 with hash_999 in memory.

Next time I give a command, I verify my identity with hash_998 , and so on. At some point, I’ll have to instruct CBot to start with a new hash chain, but that isn’t difficult at all.

The nice thing about this is that I can give commands and authentication to CBot in a public channel. There can be a whole bunch of people listening in, but they won’t be able to figure out the next “password”, and they won’t be able to reuse previous passwords to send commands to CBot.


So how can we implement this in C? Well, there’s one rule you should always follow in the world of cryptography: never do it yourself. Cryptography is very difficult to implement, so you should let somebody smarter than you implement it. So instead of trying to implement a hash function ourselves, we’ll use a handy library called OpenSSL, which happens to have a huge variety of cryptographic hash functions already implemented.

The downside of using OpenSSL is that it has pretty bad documentation. All of the documentation is in man pages, and they seem to be missing lots of information. So I’ll walk through how I got OpenSSL to do my bidding.

I haven’t yet implemented this authentication process into CBot, so instead I’ll describe my implementation of a command line program, hashchain , that does the basic operations required.

Creating a Hash Chain

OpenSSL’s main interface for using its cryptography library is through the EVP functions. These let you do common operations (like creating message digests, more commonly known as hashes) in a way that abstracts away the particular algorithm. So when you use OpenSSL’s EVP_MD functions, you can easily swap out the MD5 hash algorithm for SHA256. I even made it a command line argument!

Now let’s get down to some code. We’ll represent a hash chain with the following struct:

struct hash_chain {
  int digest_size;
  int chain_length;
  uint8_t *data;

And here is a function that will actually create a hash chain. It takes as an argument some seed data ( base along with baselen ), a hash algorithm specified by the argument type , and the length of the chain.

struct hash_chain hash_chain_create(void *base, int baselen, const EVP_MD *type,
                                    int chain_len)
  EVP_MD_CTX *ctx;
  struct hash_chain output;
  uint32_t idx = 0;

  // Allocate space for our hash chain.
  output.digest_size = EVP_MD_size(type);
  output.chain_length = chain_len; = calloc(output.chain_length, output.digest_size);

  // Hash the base data.
  ctx = EVP_MD_CTX_create();
  EVP_DigestInit_ex(ctx, type, NULL);
  EVP_DigestUpdate(ctx, base, baselen);
  EVP_DigestFinal_ex(ctx,, NULL);

  // For each remaining item in the chain, hash the previous digest.
  for (idx = 1; idx < (uint16_t)output.chain_length; idx++) {
    EVP_DigestInit_ex(ctx, type, NULL);
    EVP_DigestUpdate(ctx, + (idx - 1) * output.digest_size,
    EVP_DigestFinal_ex(ctx, + idx * output.digest_size, NULL);

  // Cleanup and return the chain.
  return output;

The meat of this function is the calls to the EVP_ functions. Here’s how they work: To start using the EVP_MD functions, you need a context object, which is of type EVP_MD_CTX . You can get a pointer to one by calling EVP_MD_CTX_create() , and destroy it using EVP_MD_CTX_destroy() . Next you have to tell your context object which algorithm you’ll be using by calling EVP_DigestInit_ex() . We took our algorithm as the argument type , so this is easy. The last argument can even specify an implementation for that algorithm, but we want to use the default implementation OpenSSL comes with. Then, you hash your data by calling EVP_DigestUpdate() with a pointer to the data to hash (and its length). You can get the actual hash value out of the context by calling EVP_DigestFinal_ex() with a pointer to where you want the data written.

You can see that this process is done twice in this function. The first time hashes the input data into the output buffer. The second time is within the for loop, where we simply keep hashing the previous data into the next hash slot.

Verifying A Hash

The code for verifying a hash should be simple, given that we have just seen how to compute a hash using OpenSSL. Here is a function that verifies that h hashes to tip , using the hash algorithm hash :

bool hash_chain_verify(const void *h, const void *tip, const EVP_MD *hash)
  EVP_MD_CTX *ctx;
  int result;
  int digest_len = EVP_MD_size(hash);
  void *data = malloc(digest_len);

  ctx = EVP_MD_CTX_create();
  EVP_DigestInit_ex(ctx, hash, NULL);
  EVP_DigestUpdate(ctx, h, digest_len);
  EVP_DigestFinal_ex(ctx, data, NULL);

  result = memcmp(data, tip, digest_len);

  return result == 0;

You can see that once more, we’re doing the same create, init, update, final, and destroy pattern. The major difference being that afterwards, we’re using memcmp() to ensure that the resulting hash of h is the same as tip .

Implementation Details: base64

In order to use these functions in a command line tool, we need to be able to output and read in our hashes. Unfortunately, hashes are just binary data, and they don’t look too pretty if you were to try to print them on the console. To solve this, we use base64 encoding. It’s a way of representing binary data using only the characters A-Z, a-z, 0-9, / , and - .

The good news is that OpenSSL has base64 encoding implemented. The bad news is that this means we need to figure out more of OpenSSL’s API.

A little searching reveals that OpenSSL has an abstraction for input and output called BIO . The idea is somewhat similar to Unix pipes. You have BIO objects that can produce data, some that consume data, and some that can filter data. For example, files can produce or consume data, while base64 is simply a filter: something that takes input data and changes the way it’s represented. So here is how we combine OpenSSL’s base64 BIO with stdout to be able to print every hash value in a hash chain:

void hash_chain_print(struct hash_chain chain, FILE *f)
  BIO *out, *b64, *bio;
  b64 = BIO_new(BIO_f_base64());
  out = BIO_new_fp(f, BIO_NOCLOSE);
  bio = BIO_push(b64, out);

  for (int i = 0; i < chain.chain_length; i++) {
    BIO_write(bio, + i * chain.digest_size, chain.digest_size);


First, we create a base64 BIO object, along with another one which will write to file f . We use BIO_push() to hook up the output of b64 to the input of out . Next, we go through each hash in the chain and call BIO_write() , which pushes the data through the base64 encoder and out into the file. BIO_flush() tells the base64 encoder that it should write out the data it’s gotten so far on a line, so that each hash value gets its own line.

Similarly, we need to be able to take base64 encoded data as input and convert it to bytes. For that, we have to do a reversed task: instead of writing data into a base64 encoder, we read it through the base64 encoder. In this case we also make use of the fact that OpenSSL lets us use an arbitrary buffer as a BIO as well. The following is a function that decodes a base64 encoded string, given that you know the original data’s length:

void *base64_decode(char *str, int explen)
  uint8_t *buf = malloc(explen);
  BIO *b = BIO_new_mem_buf(str, -1);
  BIO *b64 = BIO_new(BIO_f_base64());
  BIO_push(b64, b);
  BIO_set_flags(b64, BIO_FLAGS_BASE64_NO_NL);
  BIO_read(b64, buf, explen);
  return buf;

First, we allocate a buffer to hold our decoded data. Then, we wrap the input string in a BIO object, and we again create a base64 bio object. We combine the two BIO s together. One important thing here is that it seems like the base64 decoder normally waits for a newline before it decodes all of the data you read. We don’t want this behavior, since our input data doesn’t have a newline. So, we tell it not to wait for a newline with the BIO_FLAGS_BASE64_NO_NL flag (this was not documented by OpenSSL at all - thanks to this article for the info!).

Once all that is done, we simply need to read data through the BIO chain into our buffer, and return it back to the caller.

Putting it together

From these four functions, I was able to put together a small command line program that can create and verify hash chains. I won’t bother copying down the driver code for this program, but you can find it at GitHub . The end product can be used something like this:

$ ./hashchain create sha256 20 "secret seed here" > chain
$ tail -n 2 chain
$ ./hashchain verify gjZmdTdMNnijpZd0hhkxJSK9/IywQIQ2H5N2BiWC6w0= 5o/+3BTbOTebzIJGTI0bZPorFatbV1zu070qBSx3Z0k=
$ ./hashchain verify not-really-a-valid-hash-at-all-1234567890ab= 5o/+3BTbOTebzIJGTI0bZPorFatbV1zu070qBSx3Z0k=


From this quick implementation with OpenSSL, we can see that it’s not too difficult to create hash chains and verify hashes when we receive them. It’s not too much of a leap to see how I could apply this to my IRC bot - and I’m sure I will soon. Of course, this probably isn’t the best way to do command authentication on IRC - but it’s interesting and the implementation was fun!

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