Basic Pentesting: 2 Walkthrough

Here’s another easy VulnHub VM.

My goal this month is to increase the speed that I pop these boxes, in preparation for the OSCP.

I had already completed the first entry in the Basic Pentesting series by this author in about 20 minutes, and wanted to see if I could crack this one in under an hour as well. The author states that it is a “a moderate step up in difficulty” from the first.

Let’s dig in!


root@kali:/var/www/html# nmap -T4 -A -p-
Starting Nmap 7.70 ( ) at 2018-09-30 23:53 EDT
Nmap scan report for basic2.lan (
Host is up (0.00039s latency).
Not shown: 65529 closed ports
22/tcp   open  ssh         OpenSSH 7.2p2 Ubuntu 4ubuntu2.4 (Ubuntu Linux; protocol 2.0)
| ssh-hostkey: 
|   2048 db:45:cb:be:4a:8b:71:f8:e9:31:42:ae:ff:f8:45:e4 (RSA)
|   256 09:b9:b9:1c:e0:bf:0e:1c:6f:7f:fe:8e:5f:20:1b:ce (ECDSA)
|_  256 a5:68:2b:22:5f:98:4a:62:21:3d:a2:e2:c5:a9:f7:c2 (ED25519)
80/tcp   open  http        Apache httpd 2.4.18 ((Ubuntu))
|_http-server-header: Apache/2.4.18 (Ubuntu)
|_http-title: Site doesnt have a title (text/html).
139/tcp  open  netbios-ssn Samba smbd 3.X - 4.X (workgroup: WORKGROUP)
445/tcp  open  netbios-ssn Samba smbd 4.3.11-Ubuntu (workgroup: WORKGROUP)
8009/tcp open  ajp13       Apache Jserv (Protocol v1.3)
| ajp-methods: 
|_  Supported methods: GET HEAD POST OPTIONS
8080/tcp open  http        Apache Tomcat 9.0.7
|_http-favicon: Apache Tomcat
|_http-title: Apache Tomcat/9.0.7
MAC Address: 08:00:27:A1:01:12 (Oracle VirtualBox virtual NIC)
Device type: general purpose
Running: Linux 3.X|4.X
OS CPE: cpe:/o:linux:linux_kernel:3 cpe:/o:linux:linux_kernel:4
OS details: Linux 3.2 - 4.9
Network Distance: 1 hop
Service Info: Host: BASIC2; OS: Linux; CPE: cpe:/o:linux:linux_kernel

Host script results:
|_clock-skew: mean: 1h19m59s, deviation: 2h18m34s, median: 0s
|_nbstat: NetBIOS name: BASIC2, NetBIOS user: , NetBIOS MAC:  (unknown)
| smb-os-discovery: 
|   OS: Windows 6.1 (Samba 4.3.11-Ubuntu)
|   Computer name: basic2
|   NetBIOS computer name: BASIC2\x00
|   Domain name: \x00
|   FQDN: basic2
|_  System time: 2018-09-30T23:53:35-04:00
| smb-security-mode: 
|   account_used: guest
|   authentication_level: user
|   challenge_response: supported
|_  message_signing: disabled (dangerous, but default)
| smb2-security-mode: 
|   2.02: 
|_    Message signing enabled but not required
| smb2-time: 
|   date: 2018-09-30 23:53:35
|_  start_date: N/A

Interesting Services

We have SSH, HTTP, Samba, Apache Tomcat, and Apache Jserv exposed.

Checking Out the Website

The website just states that it’s undergoing maintenance, but there is a hint hidden in the HTML source.

Basic Pentesting 2, Port 80

Let’s see if we can find that “dev note section.”

Checking for Hidden Files

Here we run a simple Nikto scan.

nikto -h

Nikto Scan

Nikto identified a useful directory for us, /development. Let’s take a look.


dev.txt contains the following message:


Apache Struts, eh

My mind immediately goes to the Apache Struts vulnerability that’s been in the news. I sometimes see random scans for it on various servers that I manage. I’m almost positive that exploit will work to get a foothold, but for now I’ll keep digging around just for fun.

Checking the other .txt file

j.txt contains the following message:


This is a not-too-subtle suggestion to use a wordlist to attack the password for a user who’s name begins with the letter J.

Enumerating Users

This server has Samba exposed, so enum4linux may come in handy for this.

[+] Enumerating users using SID S-1-22-1 and logon username '', password ''
S-1-22-1-1000 Unix User\kay (Local User)
S-1-22-1-1001 Unix User\jan (Local User)

We’ve identified our “J” and “K” users 🙂

Dictionary Attack on SSH

Hydra should make short work of this.

hydra -l jan -P /usr/share/wordlists/rockyou.txt ssh

Hydra finds the password in about 3 minutes with 16 threads active.

SSH credentials

Privilege Escalation

Once logged in, I poked around the /home directories to see what was available. jan didn’t have anything useful, but kay had a few things worth looking at:

kay’s home dir

.ssh dir

Some good stuff here

  • pass.bak (but not readable by jan)
  • .sudo_as_admin_successful
  • .ssh files with incorrect permissions

Those .ssh files look promising

Abusing the files in .ssh looked like a strong contender for getting in and sudo’ing to root, but before I try it, I decided to run (google it) to see if there was anything else immediately available.


Identifying SUID binaries

This script identified that /usr/bin/vim.basic has SUID set. This is unusual. It means if we run the vim editor as a non-privileged user, we’ll be able to read and write all sorts of sensitive and critical files.

I chose to edit /etc/sudoers to make jan a sudo user.

vim /etc/sudoers

Editing /etc/sudoers

Vim warns us the file is supposed to be read-only, but we can override that and save it with :wq!


After exiting Vim and getting back to bash, run sudo su - to escalate to root.

Root obtained

And capturing the flag…


Other methods…

  • Instead of editing the sudoers file, we could have used the SUID vim to read /home/kay/password.bak file with vim, which contains a valid password for kay on SSH. kay already has sudo privileges.
  • As mentioned previously, we could have stolen the private key contained in /home/kay/.ssh and used this to connect by SSH.
  • Also mentioned previously was the obvious hint about Apache Struts. I’ll go over this one quickly now.

Apache Struts Method

The dev.txt file from earlier identified that they were using Apache Struts 2.5.12 and had a super cool REST demo working.

Trying Metasploit

Firing up msfconsole

exploit/multi/http/struts2_rest_xstream sounds like a winner, so we’ll try that one.

Viewing options for this exploit

The default TARGETURI selected is a 404 on port 8080, but this one does exist:

Setting our options

Running the exploit

Very useful REST demo 👌

You could then use any of the other jan steps listed above (before the metasploit section) to escalate to root.

More, please

I met my goal and cracked this box in well under an hour. The hints may have been a bit too spot on, but it was still fun.

More write-ups to come.


Did this post save you time, frustration, or money?

Leave a Reply

Your email address will not be published. Required fields are marked *

Note: Comments are moderated. Please submit the form only once.