$ file crackme crackme: ELF 64-bit LSB executable, x86-64, version 1 (SYSV), statically linked, BuildID[sha1]=92ef00b31d91a827a5aed6b0fe03fe38fe20fb4d, stripped $ ./crackme root@localhost's password: bla Permission denied (password). $ objdump -d crackme | wc -l 15809 When running objdump on it we can see obfuscation being used. The control flow graph is huge: {{ :writeups:dodo.png?direct&200 |}} Instead of diving into the assembly and wasting time trying to figure out what is happening behind the obfuscation it proved useful to do a side-channel analysis using the number of instructions. $ pin -t inscount0 -o out -- ./crackme ; cat out root@localhost's password: a Permission denied (password). Count 715821 $ pin -t inscount0 -o out -- ./crackme ; cat out root@localhost's password: b Permission denied (password). Count 716328 $ pin -t inscount0 -o out -- ./crackme ; cat out root@localhost's password: c Permission denied (password). Count 716835 $ bc -lq 716328 -715821 507 716835 - 716328 507 Interesting, let's check all the ascii characters using a script: $ python bf.py Input [!] -> [717933] delta [507] Input ["] -> [718440] delta [507] Input [#] -> [718947] delta [507] Input [$] -> [719454] delta [507] Input [%] -> [719961] delta [507] Input [&] -> [720468] delta [507] Input ['] -> [720975] delta [507] Input [(] -> [721482] delta [507] Input [)] -> [721989] delta [507] Input [*] -> [722496] delta [507] Input [+] -> [723003] delta [507] Input [,] -> [723510] delta [507] Input [-] -> [724017] delta [507] Input [.] -> [724524] delta [507] Input [/] -> [725031] delta [507] Input [0] -> [725538] delta [507] Input [1] -> [726045] delta [507] Input [2] -> [726552] delta [507] Input [3] -> [727059] delta [507] Input [4] -> [727566] delta [507] Input [5] -> [728073] delta [507] Input [6] -> [728580] delta [507] Input [7] -> [729087] delta [507] Input [8] -> [729594] delta [507] Input [9] -> [730101] delta [507] Input [:] -> [730608] delta [507] Input [;] -> [731115] delta [507] Input [<] -> [731622] delta [507] Input [=] -> [732129] delta [507] Input [>] -> [732636] delta [507] Input [?] -> [733143] delta [507] Input [@] -> [733650] delta [507] Input [A] -> [734157] delta [507] Input [B] -> [734664] delta [507] Input [C] -> [735171] delta [507] Input [D] -> [735678] delta [507] Input [E] -> [736185] delta [507] Input [F] -> [736692] delta [507] Input [G] -> [737199] delta [507] Input [H] -> [701989] delta [-35210] Input [I] -> [703653] delta [1664] Input [J] -> [704160] delta [507] Input [K] -> [704667] delta [507] Input [L] -> [705174] delta [507] Input [M] -> [705681] delta [507] Input [N] -> [706188] delta [507] Input [O] -> [706695] delta [507] Input [P] -> [707202] delta [507] Input [Q] -> [707709] delta [507] Input [R] -> [708216] delta [507] Input [S] -> [708723] delta [507] Input [T] -> [709230] delta [507] Input [U] -> [709737] delta [507] Input [V] -> [710244] delta [507] Input [W] -> [710751] delta [507] Input [X] -> [711258] delta [507] Input [Y] -> [711765] delta [507] Input [Z] -> [712272] delta [507] Input [[] -> [712779] delta [507] Input [\] -> [713286] delta [507] Input []] -> [713793] delta [507] Input [^] -> [714300] delta [507] Input [_] -> [714807] delta [507] Input [`] -> [715314] delta [507] Input [a] -> [715821] delta [507] Input [b] -> [716328] delta [507] Input [c] -> [716835] delta [507] Input [d] -> [717342] delta [507] Input [e] -> [717849] delta [507] Input [f] -> [718356] delta [507] Input [g] -> [718863] delta [507] Input [h] -> [719370] delta [507] Input [i] -> [719877] delta [507] Input [j] -> [720384] delta [507] Input [k] -> [720891] delta [507] Input [l] -> [721398] delta [507] Input [m] -> [721905] delta [507] Input [n] -> [722412] delta [507] Input [o] -> [722919] delta [507] Input [p] -> [723426] delta [507] Input [q] -> [723933] delta [507] Input [r] -> [724440] delta [507] Input [s] -> [724947] delta [507] Input [t] -> [725454] delta [507] Input [u] -> [725961] delta [507] Input [v] -> [726468] delta [507] Input [w] -> [726975] delta [507] Input [x] -> [727482] delta [507] Input [y] -> [727989] delta [507] Input [z] -> [728496] delta [507] Input [{] -> [729003] delta [507] Input [|] -> [729510] delta [507] Input [}] -> [730017] delta [507] Input [~] -> [730524] delta [507] If my assumption is correct the first letter should be "H". Let's repeat the process for the next letters, but first since inscount1 is faster than inscount0 we use it instead. A modification to the script leads to this output: $ python bf.py Trying input -> H Trying input -> H4 Trying input -> H4P Trying input -> H4PP Trying input -> H4PPY Trying input -> H4PPY_ Trying input -> H4PPY_C Trying input -> H4PPY_C0 Trying input -> H4PPY_C0D Trying input -> H4PPY_C0DE Trying input -> H4PPY_C0DEG Trying input -> H4PPY_C0DEGa Trying input -> H4PPY_C0DEGaT Trying input -> H4PPY_C0DEGaTE Trying input -> H4PPY_C0DEGaTE_ Trying input -> H4PPY_C0DEGaTE_2 Trying input -> H4PPY_C0DEGaTE_20 Trying input -> H4PPY_C0DEGaTE_201 Trying input -> H4PPY_C0DEGaTE_2014 Trying input -> H4PPY_C0DEGaTE_2014_ Trying input -> H4PPY_C0DEGaTE_2014_C Trying input -> H4PPY_C0DEGaTE_2014_CU Trying input -> H4PPY_C0DEGaTE_2014_CU_ Trying input -> H4PPY_C0DEGaTE_2014_CU_1 Trying input -> H4PPY_C0DEGaTE_2014_CU_1" Traceback (most recent call last): File "bf.py", line 52, in Ah, almost worked but it hangs because of some reason. Let's investigate: $ python bf.py Input [H4PPY_C0DEGaTE_2014_CU_1!] -> [53426] delta [-713] Input [H4PPY_C0DEGaTE_2014_CU_1"] -> [45776] delta [-7650] Input [H4PPY_C0DEGaTE_2014_CU_1#] -> [46477] delta [701] Input [H4PPY_C0DEGaTE_2014_CU_1$] -> [45776] delta [-701] Input [H4PPY_C0DEGaTE_2014_CU_1%] -> [52724] delta [6948] Input [H4PPY_C0DEGaTE_2014_CU_1&] -> [62623] delta [9899] Input [H4PPY_C0DEGaTE_2014_CU_1'] -> [45977] delta [-16646] Input [H4PPY_C0DEGaTE_2014_CU_1(] -> [45730] delta [-247] Input [H4PPY_C0DEGaTE_2014_CU_1)] -> [45729] delta [-1] Input [H4PPY_C0DEGaTE_2014_CU_1*] -> [45977] delta [248] Input [H4PPY_C0DEGaTE_2014_CU_1+] -> [45730] delta [-247] Input [H4PPY_C0DEGaTE_2014_CU_1,] -> [46506] delta [776] Input [H4PPY_C0DEGaTE_2014_CU_1-] -> [45977] delta [-529] Input [H4PPY_C0DEGaTE_2014_CU_1.] -> [47056] delta [1079] Input [H4PPY_C0DEGaTE_2014_CU_1/] -> [47110] delta [54] Input [H4PPY_C0DEGaTE_2014_CU_10] -> [45840] delta [-1270] Input [H4PPY_C0DEGaTE_2014_CU_11] -> [46473] delta [633] Input [H4PPY_C0DEGaTE_2014_CU_12] -> [38563] delta [-7910] Input [H4PPY_C0DEGaTE_2014_CU_13] -> [39030] delta [467] Input [H4PPY_C0DEGaTE_2014_CU_14] -> [38985] delta [-45] Input [H4PPY_C0DEGaTE_2014_CU_15] -> [45977] delta [6992] Input [H4PPY_C0DEGaTE_2014_CU_16] -> [38567] delta [-7410] Input [H4PPY_C0DEGaTE_2014_CU_17] -> [37877] delta [-690] Input [H4PPY_C0DEGaTE_2014_CU_18] -> [37877] delta [0] Input [H4PPY_C0DEGaTE_2014_CU_19] -> [38563] delta [686] Input [H4PPY_C0DEGaTE_2014_CU_1:] -> [37877] delta [-686] Input [H4PPY_C0DEGaTE_2014_CU_1;] -> [29361] delta [-8516] Input [H4PPY_C0DEGaTE_2014_CU_1<] -> [29277] delta [-84] Input [H4PPY_C0DEGaTE_2014_CU_1=] -> [28905] delta [-372] Input [H4PPY_C0DEGaTE_2014_CU_1>] -> [28919] delta [14] Input [H4PPY_C0DEGaTE_2014_CU_1?] -> [29228] delta [309] Input [H4PPY_C0DEGaTE_2014_CU_1@] -> [27920] delta [-1308] Input [H4PPY_C0DEGaTE_2014_CU_1A] -> [29325] delta [1405] Input [H4PPY_C0DEGaTE_2014_CU_1B] -> [20943] delta [-8382] Input [H4PPY_C0DEGaTE_2014_CU_1C] -> [20675] delta [-268] Input [H4PPY_C0DEGaTE_2014_CU_1D] -> [20681] delta [6] Input [H4PPY_C0DEGaTE_2014_CU_1E] -> [19623] delta [-1058] Input [H4PPY_C0DEGaTE_2014_CU_1F] -> [19765] delta [142] Input [H4PPY_C0DEGaTE_2014_CU_1G] -> [20682] delta [917] Input [H4PPY_C0DEGaTE_2014_CU_1H] -> [27800] delta [7118] Input [H4PPY_C0DEGaTE_2014_CU_1I] -> [20666] delta [-7134] Input [H4PPY_C0DEGaTE_2014_CU_1J] -> [19743] delta [-923] Input [H4PPY_C0DEGaTE_2014_CU_1K] -> [19766] delta [23] Input [H4PPY_C0DEGaTE_2014_CU_1L] -> [14431] delta [-5335] Input [H4PPY_C0DEGaTE_2014_CU_1M] -> [14494] delta [63] Input [H4PPY_C0DEGaTE_2014_CU_1N] -> [19765] delta [5271] Input [H4PPY_C0DEGaTE_2014_CU_1O] -> [14436] delta [-5329] Input [H4PPY_C0DEGaTE_2014_CU_1P] -> [13415] delta [-1021] Input [H4PPY_C0DEGaTE_2014_CU_1Q] -> [13438] delta [23] Input [H4PPY_C0DEGaTE_2014_CU_1R] -> [13415] delta [-23] Input [H4PPY_C0DEGaTE_2014_CU_1S] -> [13252] delta [-163] Input [H4PPY_C0DEGaTE_2014_CU_1T] -> [13415] delta [163] Input [H4PPY_C0DEGaTE_2014_CU_1U] -> [14254] delta [839] Input [H4PPY_C0DEGaTE_2014_CU_1V] -> [9118] delta [-5136] Input [H4PPY_C0DEGaTE_2014_CU_1W] -> [14248] delta [5130] Input [H4PPY_C0DEGaTE_2014_CU_1X] -> [13253] delta [-995] Input [H4PPY_C0DEGaTE_2014_CU_1Y] -> [9062] delta [-4191] Input [H4PPY_C0DEGaTE_2014_CU_1Z] -> [13252] delta [4190] Input [H4PPY_C0DEGaTE_2014_CU_1[] -> [8975] delta [-4277] Input [H4PPY_C0DEGaTE_2014_CU_1\] -> [8961] delta [-14] Input [H4PPY_C0DEGaTE_2014_CU_1]] -> [14254] delta [5293] Input [H4PPY_C0DEGaTE_2014_CU_1^] -> [14235] delta [-19] Input [H4PPY_C0DEGaTE_2014_CU_1_] -> [8964] delta [-5271] Input [H4PPY_C0DEGaTE_2014_CU_1`] -> [8154] delta [-810] Input [H4PPY_C0DEGaTE_2014_CU_1a] -> [8039] delta [-115] Input [H4PPY_C0DEGaTE_2014_CU_1b] -> [5905] delta [-2134] Input [H4PPY_C0DEGaTE_2014_CU_1c] -> [5932] delta [27] Input [H4PPY_C0DEGaTE_2014_CU_1d] -> [5858] delta [-74] Input [H4PPY_C0DEGaTE_2014_CU_1e] -> [5960] delta [102] Input [H4PPY_C0DEGaTE_2014_CU_1f] -> [5905] delta [-55] Input [H4PPY_C0DEGaTE_2014_CU_1g] -> [5869] delta [-36] Input [H4PPY_C0DEGaTE_2014_CU_1h] -> [5332] delta [-537] Input [H4PPY_C0DEGaTE_2014_CU_1i] -> [5264] delta [-68] Input [H4PPY_C0DEGaTE_2014_CU_1j] -> [5267] delta [3] Input [H4PPY_C0DEGaTE_2014_CU_1k] -> [5237] delta [-30] Input [H4PPY_C0DEGaTE_2014_CU_1l] -> [3197] delta [-2040] Input [H4PPY_C0DEGaTE_2014_CU_1m] -> [5227] delta [2030] Input [H4PPY_C0DEGaTE_2014_CU_1n] -> [3211] delta [-2016] Input [H4PPY_C0DEGaTE_2014_CU_1o] -> [1487] delta [-1724] Input [H4PPY_C0DEGaTE_2014_CU_1p] -> [1780] delta [293] Input [H4PPY_C0DEGaTE_2014_CU_1q] -> [3202] delta [1422] Input [H4PPY_C0DEGaTE_2014_CU_1r] -> [2447] delta [-755] Input [H4PPY_C0DEGaTE_2014_CU_1s] -> [2447] delta [0] Input [H4PPY_C0DEGaTE_2014_CU_1t] -> [2447] delta [0] Input [H4PPY_C0DEGaTE_2014_CU_1u] -> [1492] delta [-955] Input [H4PPY_C0DEGaTE_2014_CU_1v] -> [65] delta [-1427] Input [H4PPY_C0DEGaTE_2014_CU_1w] -> [765] delta [700] Input [H4PPY_C0DEGaTE_2014_CU_1x] -> [723] delta [-42] Input [H4PPY_C0DEGaTE_2014_CU_1y] -> [691] delta [-32] Input [H4PPY_C0DEGaTE_2014_CU_1z] -> [633] delta [-58] Input [H4PPY_C0DEGaTE_2014_CU_1{] -> [581] delta [-52] Input [H4PPY_C0DEGaTE_2014_CU_1|] -> [103] delta [-478] Input [H4PPY_C0DEGaTE_2014_CU_1}] -> [103] delta [0] Input [H4PPY_C0DEGaTE_2014_CU_1~] -> [34] delta [-69] When reverting to the slower inscount0 we get clean outputs and can continue the search: $ python bf.py Trying input -> H4PPY_C0DEGaTE_2014_CU_1N Trying input -> H4PPY_C0DEGaTE_2014_CU_1N_ Trying input -> H4PPY_C0DEGaTE_2014_CU_1N_K Trying input -> H4PPY_C0DEGaTE_2014_CU_1N_K0 Trying input -> H4PPY_C0DEGaTE_2014_CU_1N_K0R Trying input -> H4PPY_C0DEGaTE_2014_CU_1N_K0RE Output different for password [H4PPY_C0DEGaTE_2014_CU_1N_K0RE4] $ ./crackme root@localhost's password: H4PPY_C0DEGaTE_2014_CU_1N_K0RE4 SUCCESS Done! Work smart! Here's the script: #!/usr/bin/python import os, pexpect, time from subprocess import Popen,PIPE pinpath="/ctf/TOOLS/pin/pin" def try_list(lst): procs = {} ret_dict = {} for (idx, s) in enumerate(lst): out_file = s.encode('hex') p = Popen([pinpath, "-t", "inscount0", "-o", "tmp/" + out_file, "--", "./crackme"], stdout = PIPE, stdin = PIPE) procs[s] = p p.stdin.write(s + "\n") prev = 0 show_delta = False delta = {} for (idx,s) in enumerate(lst): while procs[s].poll() is None: time.sleep(0.5) if "denied" not in procs[s].stdout.read(): print "Output different for password [%s]" % s exit(-1) out_file = s.encode('hex') output = open("tmp/" + out_file).read().split(" ")[1].strip() instr_count = int(output) if show_delta: #print "Input [%s] -> [%s] delta [%s]" % (s, instr_count, instr_count - prev) delta[s] = instr_count - prev else: show_delta = True prev = instr_count for (idx,s) in enumerate(lst): if idx < 2: continue if delta[s] != delta[lst[idx-1]]: return s prefix = "" while True: lst = [prefix + chr(i) for i in range(32,127)] prefix = try_list(lst) print "Trying input -> %s" % prefix