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Nov 15, 2017 - 9 minute read - Comments - winappdbg reverse engineering CTF

WinAppDbg - Part 4 - Bruteforcing FlareOn 2017 - Challenge 3

Previous parts:

We have learned some good stuff. In this part I am going to talk about the original problem that led me to learning WinAppDbg. This is my writeup for challenge 3 "Greek to me" of FlareOn 2017. This is a bruteforce challenge and is rather easy but instead of bruteforcing it the conventional (and straightforward way), I will show how I traversed arbitrary Assembly blobs using WinAppDbg.

I will (hopefully) mostly talk about solving the challenge and not a lot of recon or other places I was stuck at.

Code is in my clone:



Run strings on the binary. On Windows I have two favorites:

  • strings from Cygwin's binutils package.
  • strings from Sysinternals.

Running strings (from Sysinternals) we get:

  • -nobanner: do not display banner.
  • -o: print the offset of the string (useful in case we want to use find the string in the file).
PS > .\SysinternalsSuite\strings.exe -o -nobanner .\3-GreektoMe\greek_to_me.exe
0077:!This program cannot be run in DOS mode.
1584:Nope, that's not it.
1608:Congratulations! But wait, where's my flag?

WS2_32.dll is the Windows socket library. So network connectivity.

Here's some interesting but unrelated info that I found when searching for the DLL: means the application has network connectivity. It's either trying to connect to a port on localhost or listening on some port.

To discover, run procmon or Wireshark:

Nothing. So it's listening on localhost.

Run the app and use netstat -anb in an Admin command prompt (needed for the b switch).

 TCP              LISTENING       5816

Application is listening on port 2222.

Short Analysis

The application is listening on port 2222. When it receives data, it uses the first byte (and only the first byte) of our input as we see here:

.text:00401029 loc_401029:      ; CODE XREF: sub_401008+1A
.text:00401029          mov     ecx, offset loc_40107C
.text:0040102E          add     ecx, 79h
.text:00401031          mov     eax, offset loc_40107C
.text:00401036          mov     dl, [ebp+buf]   ; first byte of input moved to dl

Now dl points to the first byte that we sent to the socket.

.text:00401039 loc_401039:      ; CODE XREF: sub_401008+3D
.text:00401039          mov     bl, [eax]   ; bl = grab a byte from blob
.text:0040103B          xor     bl, dl      ; bl = blob_byte xor our_first_byte
.text:0040103D          add     bl, 22h     ; bl += 0x22
.text:00401040          mov     [eax], bl   ; *eax = bl
.text:00401042          inc     eax         ; eax++ (next char)
.text:00401043          cmp     eax, ecx    ; ecx is the address of the second section
.text:00401045          jl      short loc_401039 ; check if we have reached the next section

It grabs some data (0x79 or 121 bytes to be exact) from 0x40107C, XOR-es them with our first byte and then add 0x22.

The data is some blob at offset loc_40107C.

33 E1 C4 99 11 06 81 16 F0 32 9F C4 91 17 06 81
14 F0 06 81 15 F1 C4 91 1A 06 81 1B E2 06 81 18
F2 06 81 19 F1 06 81 1E F0 C4 99 1F C4 91 1C 06
81 1D E6 06 81 62 EF 06 81 63 F2 06 81 60 E3 C4
99 61 06 81 66 BC 06 81 67 E6 06 81 64 E8 06 81
65 9D 06 81 6A F2 C4 99 6B 06 81 68 A9 06 81 69
EF 06 81 6E EE 06 81 6F AE 06 81 6C E3 06 81 6D
EF 06 81 72 E9 06 81 73 7C
XOR and ADD instructions XOR and ADD instructions

Then this modified blob (after XOR and add) is passed to sub_4011E6 and processed:

.text:00401047          mov     eax, offset loc_40107C  ; eax = *modified_blob
.text:0040104C          mov     [ebp+var_C], eax        ; varC = eax
.text:0040104F          push    79h                     ; length of modified_blob
.text:00401051          push    [ebp+var_C]
.text:00401054          call    sub_4011E6              ; sub_4011E6(*modified_blob, 0x79)
.text:00401059          pop     ecx
.text:0040105A          pop     ecx
.text:0040105B          movzx   eax, ax
.text:0040105E          cmp     eax, 0FB5Eh ; compare return value with 0xFB5E

.text:00401063          jz      short loc_40107C
.text:00401065          push    0               ; flags
.text:00401067          push    14h             ; len
.text:00401069          push    offset buf      ; "Nope, that's not it."
.text:0040106E          push    [ebp+s]         ; s
.text:00401071          call    ds:send
.text:00401077          jmp     loc_401107

Return value of the sub_4011E6 is compared with 0xFB5E. If they do not match, jz will not be taken and execution will continue. Application will send back Nope, that's not it..

Result comparison Result comparison

Now here it gets interesting. If the results match, it will jump to the section which houses the blob we just modified and attempts to execute it as code. If the application does not crash and reaches the end, it will send back Congratulations!

In other words, our first byte is supposed to transform that blob into valid assembly opcodes.

Now we could solve this is in different ways. I think everyone solved it by opening a socket, sending 256 possible bytes and looking at the response. I think it's the way the challenge was meant to be solved.

Bruteforcing with WinAppDbg

I solved it a different way. Originally I went down the rabbit hole and tried to RE sub_4011E6. That was a shit-show. Then I realized I can use WinAppDbg to bruteforce the "crypto" in-memory. We need to learn a bit more about WinAppDbg to reproduce it.

Breakpoints in WinAppDbg

WinAppDbg allows us to set breakpoints at arbitrary addresses:

Setting a breakpoint
debug.break_at(pid, address, action_callback)

def action_callback(event):
    # do something

When the breakpoint is hit, the action_callback function is called. We have not seen this before but all of our hooking has been performed internally with these instructions.

More info:

Getting and Setting Memory

WinAppDbg allows us to save/restore memory and context.

Getting and Setting Context

Context contains register and flag values. It's per thread (instead of per process like memory).

Note: After setting the context, we need to manually change the program counter to start execution at a specific location. For example if we grab the context, change Eip to an address and set it, the program counter will not change. After setting the context, manually change the program counter to your desired address with thread.set_pc(address).

For both memory and context operations, make sure to suspend the process/thread first and resume it after the operation is done.

Battle Plan

Now that we have the building blocks, we need to device a battle plan. It's very straightforward.

  1. Run the application.
  2. Set breakpoints at 0x401036 and 0x40105B.
  3. Open a socket and send any random byte.
  4. At breakpoint 0x401036:
    • If it's first_time:
      • Save memory, context and blob at 0x40107C.
    • context["Edx"] = key - swap the key.
    • key++.
    • Bypass the key assignment instruction and manually jump to 0x401039 with:
      • thread.set_pc(0x401039)
  5. At breakpoint 0x40105B:
    • If function return value is 0xFB5E, print key.
    • Else:
      • Restore memory, context and blob at 0x40107C (blob has been modified so it needs to be restored to the original bytes).
      • Go back to 0x401036 with thread.set_pc(0x401036)
Bruteforcing plan Bruteforcing plan

It would have been easier to change the first byte of buf instead of edx and avoiding the jump labeled 2 in the picture.

Bruteforcing in Action

Code is in the repo and named 19-GreekToMe.py. You need to place greek_to_me.exe in the same directory. It's not in the repo so you need to download it from the website.

That was pretty fast because our address space was only one byte (0x00 to 0xFF).

$ python 19-GreekToMe.py
[21:23:48.0743] Starting simple_debugger
[21:23:48.0753] Started simple_debugger. Sleeping for 2 seconds.
[21:23:50.0756] Starting send_me.
[21:23:50.0875] Socket connected
[21:23:50.0875] Sent 0
Key: 0xa2
Eax: 0000FB5E
[21:23:54.0901] Reached 0x100


Run the application in a debugger, set a breakpoint at the "Congratulations!" instruction and send 0xA2. The blob results in the correct instructions and we get the flag.

flag: et_tu_brute_force@flare-on.com

Some More Analysis - Optional Read

This part is optional but I had already written them during the challenge.

Start of the app:

public start
start proc near
call    sub_401008
xor     eax, eax
start endp

sub_401008 is called, then app returns 0 and exits.

Inside sub_401008 we see another subroutine sub_401121. Before that a *buf is pushed (as an argument) and is empty.


We can see the socket being constructed with WSAStartup:

lea     eax, [ebp+WSAData]
push    eax             ; lpWSAData
push    202h            ; wVersionRequested
call    ds:WSAStartup
test    eax, eax
jz      short loc_401147

Then if WSAStartup was successful we can see the port and other parameters being passed to socket. IDA highlights a lot of them for us.

push    esi
push    edi
push    6               ; protocol
push    1               ; type
push    2
pop     edi
push    edi             ; af
call    ds:socket
mov     esi, eax
cmp     esi, 0FFFFFFFFh
jz      short loc_4011D8

We can see socket here. And of course the arguments are pushed to the stack from right to left.

  • af = 2 = AF_INET = IPv4
  • type = 1 = SOCK_STREAM = TCP socket
  • protocol = 6 = IPPROTO_TCP = TCP

The string is being converted to an inet address with inet_addr.

push    offset cp       ; ""
mov     [ebp+name.sa_family], di
call    ds:inet_addr

Then port with htons.

push    8AEh            ; hostshort
mov     dword ptr [ebp+name.sa_data+2], eax
call    ds:htons

"The htons function converts a u_short from host to TCP/IP network byte order (which is big-endian)."

Port number 0x8AE is 2222 decimal.

Then bind:

mov     word ptr [ebp+name.sa_data], ax
lea     eax, [ebp+name]
push    10h             ; namelen
push    eax             ; name
push    esi             ; s
call    ds:bind

"The bind function associates a local address with a socket."

After there is listen, accept and recv but we already know what they do.

Finally we are listening on

Let's take a closer look at recv.

"The recv function receives data from a connected socket or a bound connectionless socket."

push    0               ; flags
push    4               ; len
push    [ebp+buf]       ; buf
push    edi             ; s
call    ds:recv
test    eax, eax
jle     short loc_4011CA

Buf from the parameter is going to be the pointer to the data received. recv returns the number of bytes received (which going to be in eax).

If nothing was received, the jle is successful and socket is closed.

Otherwise the function returns the number of received bytes.

The rest is explained above.


I think I am going to stop writing back-to-back blogs for a few days. I have had 0 off-time. But I am glad I learned WinAppDbg, it will help me a lot in my day job.

As usual if you have any suggestions or catch any errors, feel free to contact me.