One of the uses of Tigress is as an educational tool. The --Transform=RandomFuns option will generate a random function that can subsequently be transformed using any combination of Tigress obfuscations, and then given to students as a cracking target.

You can generate a program for the students to reverse engineer:

or you can generate a program for them to crack:

Depending on the sophistication of your students, you can vary the length of the transformation sequence, the difficulty of the transformations, the options to the transformations, the complexity of the generated challenge function, and either give them source to untangle (a good way to learn about particular transformations), or stripped compiled code (for a more real-world challenge).

We typically give each student 3 programs, of different levels of difficulty, to attack. Thanks to the diversity of Tigress-generated programs, each challenge is unique, making it harder for students to cheat.



Below is part of the script we use to generate take-home exams for our students. It contains two assets, a password check and an expired time check, and it's the students' job to disable these.

Start by creating this file, empty.c
#include "apple.h"
# Generate the cleartext challenge program. This is hidden from the students.
tigress --Verbosity=1 --Seed=$seed6 --Environment=x86_64:Darwin:Clang:5.1 \
      --Transform=RandomFuns \
         --RandomFunsName=SECRET \
         --Verbosity=5 \
         --RandomFunsFunctionCount=1 \
         --RandomFunsTrace=0 \
         --RandomFunsType=long \
         --RandomFunsInputSize=1 \
         --RandomFunsLocalStaticStateSize=1 \
         --RandomFunsGlobalStaticStateSize=0 \
         --RandomFunsLocalDynamicStateSize=0 \
         --RandomFunsGlobalDynamicStateSize=0 \
         --RandomFunsBoolSize=2 \
         --RandomFunsLoopSize=1000 \
         --RandomFunsCodeSize=100 \
         --RandomFunsOutputSize=1 \
         --RandomFunsTimeCheckCount=1 \
         --RandomFunsActivationCodeCheckCount=1 \
         --RandomFunsActivationCode=42 \
         --RandomFunsPasswordCheckCount=1 \
         --RandomFunsPassword=secret \
         --RandomFunsFailureKind=segv \
      --out=6-input.c empty.c

# Generate an empty program with the same interface as the challenge program
# for the students to fill out
tigress --Verbosity=1 --Seed=$seed6 \
      --Transform=RandomFuns --RandomFunsName=SECRET \
         --RandomFunsType=long \
         --RandomFunsInputSize=1 \
         --RandomFunsLocalStaticStateSize=1 \
         --RandomFunsGlobalStaticStateSize=0 \
         --RandomFunsLocalDynamicStateSize=0 \
         --RandomFunsGlobalDynamicStateSize=0 \
         --RandomFunsOutputSize=1 \
         --RandomFunsCodeSize=0 \
      --out=6-answer.c empty.c

# Obfuscate the challenge program. 
tigress --Verbosity=1 --Seed=$seed6 --FilePrefix=obf \
      --Transform=InitEntropy \
      --Transform=InitOpaque \
         --Functions=main --InitOpaqueCount=1 --InitOpaqueStructs=list,array\
      --Transform=InitBranchFuns \
      --Transform=EncodeLiterals \
         --Functions=SECRET --EncodeLiteralsKinds=string --EncodeLiteralsEncoderName=STRINGS\
      --Transform=Virtualize \
         --Functions=STRINGS --VirtualizeDispatch=switch --VirtualizeOperands=stack,registers \
         --VirtualizeMaxMergeLength=2 --VirtualizeSuperOpsRatio=1.0 \
      --Transform=AddOpaque \
         --Functions=SECRET --AddOpaqueKinds=call,bug,true --AddOpaqueCount=4\
      --Transform=Virtualize \
         --Functions=SECRET --VirtualizeDispatch=indirect --VirtualizeOperands=stack,registers \
         --VirtualizeMaxMergeLength=2 --VirtualizeSuperOpsRatio=1.0 \
      --Transform=Virtualize \
         --Functions=SECRET --VirtualizeDispatch=ifnest --VirtualizeOperands=stack,registers \
         --VirtualizeMaxMergeLength=2 --VirtualizeSuperOpsRatio=1.0 --VirtualizeNumberOfBogusFuns=1\
      --Transform=EncodeLiterals \
         --Functions=SECRET --EncodeLiteralsKinds=integer \
       --Transform=BranchFuns \
         --Functions=SECRET --BranchFunsFlatten=true \
      --Transform=CleanUp \
         --CleanUpKinds=annotations,constants,names \
      --out=6-challenge.c 6-input.c

Structure of Random Programs

To fulfill our needs, a random program generator must have certain characteristics:

The generated challenge programs all take the following simple form:

#include ≤stdio.h> 
#include ≤stdlib.h>

void SECRET(unsigned long input[1] , unsigned long output[1] ) 
int main(int argc, char** argv) {
  unsigned long input[1] ;
  unsigned long output[1] ;
  int i5 ;
  unsigned long value6 ;
  int i7 ;
  i5 = 0;
  while (i5 < 1) {
    value6 = strtoul(argv[i5 + 1], 0, 10);
    input[i5] = value6;
    i5 ++;
  SECRET(input, output);
  i7 = 0;
  while (i7 < 1) {
    printf("%lu\n", output[i7]);
    i7 ++;

That is, a challenge program reads one or more longs from standard in, and produces one or more longs on standard out.

Internally, generated SECRET functions share the same basic structure: an expansion phase, a mixing phase, and a compression phase:

Here is an example:
void SECRET(unsigned long input[1] , unsigned long output[1] ) { 
  unsigned long state[4] ;
  unsigned long local1 ;

  /* Expansion phase */
  state[0UL] = input[0UL] + 762537946UL;
  state[1UL] = input[0UL] | ((16601096UL << (state[0UL] % 16UL | 1UL)) | (16601096UL >> (64 - (state[0UL] % 16UL | 1UL))));
  state[2UL] = (input[0UL] ^ 643136481UL) ^ (state[0UL] + 292656718UL);
  state[3UL] = (input[0UL] << (((state[1UL] >> 4UL) & 15UL) | 1UL)) | (input[0UL] >> (64 - (((state[1UL] >> 4UL) & 15UL) | 1UL)));

  /* Mixing phase */
  local1 = 0UL;
  while (local1 < 3UL) {
    state[1UL] |= (state[2UL] & 15UL) << 3UL;
    state[local1 + 1UL] = state[local1];
    local1 += 2UL;
  if ((state[0UL] | state[1UL]) > (state[2UL] | state[3UL])) {
    state[3UL] |= (state[1UL] & 31UL) << 3UL;
  } else {
    state[2UL] = state[0UL];
    state[3UL] |= (state[2UL] & 15UL) << 3UL;
  state[0UL] = state[2UL];

  /* Compression phase */  
  output[0UL] = (state[0UL] << (state[1UL] % 8UL | 1UL)) << ((((state[2UL] << (state[3UL] % 8UL | 1UL)) >> 1UL) & 7UL) | 1UL);


--Transform RandomFuns Generate a random function useful as an attack target.
--RandomFunsFunctionFunctionCount INTSPEC Number of functions to generate. Default=1.
--RandomFunsTrace INTSPEC Insert tracing in the generated program. 0=no tracing. 1=trace function entry and exit. 2=as 1, but also trace control points. 3=as 2, but also trace individual statements. 4=as 3, but also trace the values of the STATE variable at each statement. Default=0.
--RandomFunsInputSize INTSPEC Size of input. Default=1.
--RandomFunsLocalStaticStateSize INTSPEC Size of function-local static state. Default=1.
--RandomFunsLocalDynamicStateSize INTSPEC Size of function-local dynamic state, i.e. the number of linked structures (lists, trees, etc) that can be built. Default=0.
--RandomFunsGlobalStaticStateSize INTSPEC Size of global static state. Default=0.
--RandomFunsGlobalDynamicStateSize INTSPEC Size of global dynamic state, i.e. the number of linked structures (lists, trees, etc) that can be built. Default=0.
--RandomFunsOutputSize INTSPEC Size of output. Default=1.
--RandomFunsCodeSize INTSPEC Size of the generated code. This is the number of nodes in generated Abstract Syntax Tree. Default=10.
--RandomFunsLoopSize INTSPEC Maximum count of loop iterations. Used to control the length of execution. Default=None.
--RandomFunsBoolSize INTSPEC Size of boolean expressions, specifically the number of conjunctions and disjunctions (&& and ||) that are used to build up expressions. Default=1.
--RandomFunsType char, short, int, long, float, double Type of input/output/state. Default=long.
  • char = C int type
  • short = C int type
  • int = C int type
  • long = C long type
  • float = C float type
  • double = C double type
--RandomFunsName string The name of the generated function.
--RandomFunsFailureKind message, abort, segv The manner in which a triggered asset may fail. Comma-separated list. Default=segv.
  • message = Print a message.
  • abort = Call the abort function.
  • segv = Die with a segmentation fault.
--RandomFunsInputKind argv, stdin How inputs are read by the program, through the command line or stdin. Default=argv.
  • argv = Enter input to the program on the command line.
  • stdin = Enter input to the program through stdin.
--RandomFunsDummyFailure BOOLSPEC Generates excatly the same code whether true or false, except the failure code is rendered impotent. In other words, --RandomFunsDummyFailure=true will have the failure code inserted, but inactive. Default=false.
--RandomFunsActivationCode int The code the user has to enter (as the first command line arguments) to be allowed to run the program. Default=42.
--RandomFunsPassword string The password the user has to enter (read from standar input) to be allowed to run the program. Default="42".
--RandomFunsTimeCheckCount int The number of checks for expired time (gettimeofday() > someTimeInThePast) to be inserted in the program. Default=0.
--RandomFunsActivationCodeCheckCount int The number of checks for correct activation code to be inserted in the program. Default=0.
--RandomFunsPasswordCheckCount int The number of checks for correct password to be inserted in the program. Probably only 0 and 1 make sense here, since the user will be prompted for a password once for every check. Default=0.
--RandomFunsControlStructures S-Expression If set, will define the nested control structures of the generated function. Otherwise, a random structure will be generated. The argument is an S-Expression, where each subexpression has one of the forms (bb INTSPEC) (for a basic block consisting of a certain number of assignment statements), (for S-expression) (for a for-loop with a given body), or (if S-expression S-expression) (for an if-statement with a given then and else part), or (switch S-expression S-expression) (for a switch-statement with a given list of cases and a default case). For example, --RandomFunsControlStructures='(for ((bb 4)))' will generate a body consisting of a for-loop with 4 assignment statements in the body. (for ((bb 4) (if ((bb 1)) ((bb 2))))) also puts an if-statement inside the loop. (for ((bb 4) (if ((bb 1)) ((for (bb 2)))))) puts a for-loop inside the else-part of the if-statement. (switch ((bb 4) (if ((bb 1)))) (bb 4)) creates a switch-statment with two cases (a basic block and an if-statement), and a basic block as the default case,. Default=none.
--RandomFunsBasicBlockSize INTSPEC The size of basic blocks, when control structures are not explicitly specified using RandomFunsControlStructures. Default=3.
--RandomFunsForBound constant, input, boundedInput, boundedAny The allowable upper bound in a for-statement. Comma-separated list. Default=constant.
  • constant = Literal integer.
  • input = Value from the input array, could cause index out of bounds.
  • boundedInput = Value from the input array, will not cause index out of bounds.
  • boundedAny = Value from the any source, will not cause index out of bounds.
--RandomFunsOperators PlusA, MinusA, Mult, Div, Mod, Shiftlt, Shiftrt, Lt, Gt, Le, Ge, Eq, Ne, BAnd, BXor, BOr, * The allowable operators in expressions. Comma-separated list. Default=all.
  • PlusA = +
  • MinusA = -
  • Mult = *
  • Div = /
  • Mod = %
  • Shiftlt = <<
  • Shiftrt = >>
  • Lt = <
  • Gt = >
  • Le = =<
  • Ge = >=
  • Eq = ==
  • Ne = !=
  • BAnd = &
  • BXor = ^
  • BOr = |
  • * = all operators
--RandomFunsPointTest BOOL Add if (output[0] == 4242424242U) printf("You win!\n"); after the call to the generated function. The idea is to replace (by hand) 4242424242U with one actual output of the function. This can be used as another reverse engineering challenge: "Find an input for which the program prints "You win!. Default=false.




Random function generation is described in Predicting the Resilience of Obfuscated Code Against Symbolic Execution Attacks via Machine Learning by Sebastian Banescu, Christian Collberg, and Alexander Pretschner, USENIX Security 2017.