Cryptopals Diversion 2 - Simulating Time Leaks


A little detour that will help in Challenge 31 in Cryptopals.

Cryptopals Challenge 31 is about taking advantage of programmers’ instinct on making stuff as efficient as possible.

In this case, if we’re comparing two strings char by char and find two differing ones, what’s the point of going forward to compare the other ones? Of course we can just return false and move on.

Except that this leaks information. If an attacker tries all characters and one of them takes longer, it’s a big hint that this is the right one. Pair this with the fact that giving the right string is your key to validate a request and you have a perfect recipe for being pwned.

Well, not that fast. Or, better, not when fast.

If the difference is in the realm of micro or nanoseconds, and we’re doing a remote attack on a web service with typical millisecond-range answer times, is the attacker really going to exploit us? Maybe not, but let’s not be lazy.

To warm up our attacking skills, the challenge suggests this:

Write a function, call it insecure_compare, that implements the == operation by doing byte-at-a-time comparisons with early exit (ie, return false at the first non-matching byte).

In the loop for insecure_compare, add a 50ms sleep (sleep 50ms after each byte).

This is where the artificial time leak comes out in the challenge’s title.

Perl’s default sleep function takes an integer number of seconds as input, which is a bit too much in our case. Luckily enough, CORE module Time::HiRes comes to the rescue, providing us support for floating point inputs, resulting in sub-second capabilities.

I initially coded insecure_compare –well, unsafe_compare as I actually named it– like this:

use Time::HiRes qw< sleep >;
our $DRAG_DELAY = $ENV{DRAG_DELAY} // (50 / 1000); # 50 ms default

sub unsafe_compare ($x, $y) {
   return 0 if length($x) != length($y); # early exit

   for my $i (0 .. length($x) - 1) {
      return 0 if substr($x, $i, 1) ne substr($y, $i, 1);

   return 1;

sub drag { sleep $DRAG_DELAY }

After each successful comparison (starting with the string length) we have a delay, simulating the huge amount of operations to compare two characters.

The delay is introduced using the drag function, driven by the $DRAG_DELAY which is set to 50 ms by default.

We might argue that the delay should actually come before the comparison, as it should simulate a slow comparison function. Whatever, in my code there’s a call to drag() before comparing the first pair, so the only “wrong” thing is calling it after the last pair was successful. Whatever.

This proved to be problematic while attacking the code. Fact is, the time length I could get out of it were sometimes quite impredictable. On the one hand this was a bless, because it forced me to find a better algorithm to code the attack, but this is for another post.

There are two aspects that make this approach a questionable candidate for simulating a leaking comparison function:

  • the sleep function introduces noise of itself, which should hardly appear in the original leaky comparison function where the operations should be much more deterministic. This means that we will generally end up with more time. Calling this multiple times will spread out the uncertainty, up to the point where the uncertainty can give us false positives.
  • The sleep function might be interrupted, so we might end up with less time, which might lead to false negatives.

I have to admit that I didn’t explicitly test for the latter. I don’t know if an interrupted call to sleep is restarted automatically, but still it might be worth to defend against this, especially considering that different platforms might behave differently.

So I decided to enhance the simulation and do this instead:

  • accumulate how much delay to introduce by counting the number of equal characters;
  • perform the delay all in one sweep, based on the count in the bullet above. Additionally, make sure to at least wait what is expected, doing more sleeping in case it was not enough (e.g. due to some interruption).

This is the resulting code:

use Time::HiRes qw< sleep time >;
our $DRAG_DELAY = $ENV{DRAG_DELAY} // (50 / 1000); # 50 ms default

sub unsafe_compare ($x, $y) {
   return 0 if length($x) != length($y);

   my $n = 1;
   for my $i (0 .. length($x) - 1) {
      last if substr($x, $i, 1) ne substr($y, $i, 1);

   return $n > length($x);

sub drag ($n) {
   my $amount = $n * $DRAG_DELAY;
   while ($amount > 0) {
      my $start = time();
      sleep $amount;
      $amount -= (time() - $start);

This proved to be a better simulation, which also resulted in better performance from my algorithm for cracking it. This is, anyway, matter for another post.

Stay safe and secure!

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