Apache Tomcat
Apache Tomcat is an open-source web server that hosts applications written in Java. Tomcat was initially designed to run Java Servlets and Java Server Pages (JSP) scripts. However, its popularity increased in Java-based frameworks and is now widely used by frameworks such as Spring and tools such as Gradle. According to data gathered by BuiltWith there are over 220,000 live Tomcat websites at this time. Here are a few more interesting statistics:
BuiltWith has gathered data that shows that over 904,000 websites have at one point been using Tomcat
1.22% of the top 1 million websites are using Tomcat, while 3.8% of the top 100k websites are
Tomcat holds position # 13 for web servers by market share
Some organizations that use Tomcat include Alibaba, the United States Patent and Trademark Office (USPTO), The American Red Cross, and the LA Times
Tomcat - Discovery & Enumeration
Tomcat servers can be identified by the Server header in the HTTP response. If the server is operating behind a reverse proxy, requesting an invalid page should reveal the server and version. Here we can see that Tomcat version 9.0.30 is in use.

Custom error pages may be in use that do not leak this version information. In this case, another method of detecting a Tomcat server and version is through the /docs page.
Identify Tomcat
This is the default documentation page, which may not be removed by administrators. Here is the general folder structure of a Tomcat installation.
Tomcat - Discovery & Enumeration
The bin folder stores scripts and binaries needed to start and run a Tomcat server. The conf folder stores various configuration files used by Tomcat. The tomcat-users.xml file stores user credentials and their assigned roles. The lib folder holds the various JAR files needed for the correct functioning of Tomcat. The logs and temp folders store temporary log files. The webapps folder is the default webroot of Tomcat and hosts all the applications. The work folder acts as a cache and is used to store data during runtime.
Each folder inside webapps is expected to have the following structure.
Tomcat - Discovery & Enumeration
The most important file among these is WEB-INF/web.xml, which is known as the deployment descriptor. This file stores information about the routes used by the application and the classes handling these routes. All compiled classes used by the application should be stored in the WEB-INF/classes folder. These classes might contain important business logic as well as sensitive information. Any vulnerability in these files can lead to total compromise of the website. The lib folder stores the libraries needed by that particular application. The jsp folder stores Jakarta Server Pages (JSP), formerly known as JavaServer Pages, which can be compared to PHP files on an Apache server.
Here’s an example web.xml file.
The web.xml configuration above defines a new servlet named AdminServlet that is mapped to the class com.inlanefreight.api.AdminServlet. Java uses the dot notation to create package names, meaning the path on disk for the class defined above would be:
classes/com/inlanefreight/api/AdminServlet.class
Next, a new servlet mapping is created to map requests to /admin with AdminServlet. This configuration will send any request received for /admin to the AdminServlet.class class for processing. The web.xml descriptor holds a lot of sensitive information and is an important file to check when leveraging a Local File Inclusion (LFI) vulnerability.
The tomcat-users.xml file is used to allow or disallow access to the /manager and host-manager admin pages.
The file shows us what each of the roles manager-gui, manager-script, manager-jmx, and manager-status provide access to. In this example, we can see that a user tomcat with the password tomcat has the manager-gui role, and a second weak password admin is set for the user account admin
Enumeration
After fingerprinting the Tomcat instance, unless it has a known vulnerability, we'll typically want to look for the /manager and the /host-manager pages. We can attempt to locate these with a tool such as Gobuster or just browse directly to them.
Tomcat - Discovery & Enumeration
We may be able to either log in to one of these using weak credentials such as tomcat:tomcat, admin:admin, etc. If these first few tries don't work, we can try a password brute force attack against the login page, covered in the next section. If we are successful in logging in, we can upload a Web Application Resource or Web Application ARchive (WAR) file containing a JSP web shell and obtain remote code execution on the Tomcat server.
Custom error pages may be in use that do not leak this version information. In this case, another method of detecting a Tomcat server and version is through the /docs page.
Tomcat - Discovery & Enumeration
This is the default documentation page, which may not be removed by administrators. Here is the general folder structure of a Tomcat installation.
Tomcat - Discovery & Enumeration
The bin folder stores scripts and binaries needed to start and run a Tomcat server. The conf folder stores various configuration files used by Tomcat. The tomcat-users.xml file stores user credentials and their assigned roles. The lib folder holds the various JAR files needed for the correct functioning of Tomcat. The logs and temp folders store temporary log files. The webapps folder is the default webroot of Tomcat and hosts all the applications. The work folder acts as a cache and is used to store data during runtime.
Each folder inside webapps is expected to have the following structure.
The most important file among these is WEB-INF/web.xml, which is known as the deployment descriptor. This file stores information about the routes used by the application and the classes handling these routes. All compiled classes used by the application should be stored in the WEB-INF/classes folder. These classes might contain important business logic as well as sensitive information. Any vulnerability in these files can lead to total compromise of the website. The lib folder stores the libraries needed by that particular application. The jsp folder stores Jakarta Server Pages (JSP), formerly known as JavaServer Pages, which can be compared to PHP files on an Apache server.
Here’s an example web.xml file.
The web.xml configuration above defines a new servlet named AdminServlet that is mapped to the class com.inlanefreight.api.AdminServlet. Java uses the dot notation to create package names, meaning the path on disk for the class defined above would be:
classes/com/inlanefreight/api/AdminServlet.class
Next, a new servlet mapping is created to map requests to /admin with AdminServlet. This configuration will send any request received for /admin to the AdminServlet.class class for processing. The web.xml descriptor holds a lot of sensitive information and is an important file to check when leveraging a Local File Inclusion (LFI) vulnerability.
The tomcat-users.xml file is used to allow or disallow access to the /manager and host-manager admin pages.
The file shows us what each of the roles manager-gui, manager-script, manager-jmx, and manager-status provide access to. In this example, we can see that a user tomcat with the password tomcat has the manager-gui role, and a second weak password admin is set for the user account admin
After fingerprinting the Tomcat instance, unless it has a known vulnerability, we'll typically want to look for the /manager and the /host-manager pages. We can attempt to locate these with a tool such as Gobuster or just browse directly to them.
Tomcat - Discovery & Enumeration
We may be able to either log in to one of these using weak credentials such as tomcat:tomcat, admin:admin, etc. If these first few tries don't work, we can try a password brute force attack against the login page, covered in the next section. If we are successful in logging in, we can upload a Web Application Resource or Web Application ARchive (WAR) file containing a JSP web shell and obtain remote code execution on the Tomcat server.
Attack
If we can access the /manager or /host-manager endpoints, we can likely achieve remote code execution on the Tomcat server.
Brutefoce the tomcat manager page and the login credentials using Burp Suite Intruder or this Metasploit module: auxiliary/scanner/http/tomcat_mgr_login:
If you want to route the metasploit traffic to your Proxy (e.g. BurpSuite), use the following option in Metasploit:
Tomcat Apache default configuration uses basic authentication, if you route your traffic to your Proxy server, you will see something like that:

A quick check of the value in the Authorization header for one request shows that the scanner is running correctly, base64 encoding the credentials admin:vagrant the way the Tomcat application would do when a user attempts to log in directly from the web application. Attacking Tomcat
Tomcat malicious WAR file upload
This interface is available at /manager/html by default, which only users assigned the manager-gui role are allowed to access. Valid manager credentials can be used to upload a packaged Tomcat application (.WAR file) and compromise the application. A WAR, or Web Application Archive, is used to quickly deploy web applications and backup storage.

The manager web app allows us to instantly deploy new applications by uploading WAR files. A WAR file can be created using the zip utility. A JSP web shell such as this can be downloaded and placed within the archive.
Code: java
Attacking Tomcat
Click on Browse to select the .war file and then click on Deploy.

This file is uploaded to the manager GUI, after which the /backup application will be added to the table.

If we click on backup, we will get redirected to http://web01.inlanefreight.local:8180/backup/ and get a 404 Not Found error. We need to specify the cmd.jsp file in the URL as well. Browsing to http://web01.inlanefreight.local:8180/backup/cmd.jsp will present us with a web shell that we can use to run commands on the Tomcat server.
We could also use msfvenom to generate a malicious WAR file.
The payload java/jsp_shell_reverse_tcp will execute a reverse shell through a JSP file. Browse to the Tomcat console and deploy this file. Tomcat automatically extracts the WAR file contents and deploys it.
Start a Netcat listener and click on /backup to execute the shell.
Alternative and discret JSP files
This JSP web shell is very lightweight (under 1kb) and utilizes a Bookmarklet or browser bookmark to execute the JavaScript needed for the functionality of the web shell and user interface. Without it, browsing to an uploaded cmd.jsp would render nothing. This is an excellent option to minimize our footprint and possibly evade detections for standard JSP web shells (though the JSP code may need to be modified a bit).
The web shell as is only gets detected by 2/58 anti-virus vendors.

to:
results in 0/58 security vendors flagging the cmd.jsp file as malicious at the time of writing.
CVE-2020-1938 : Ghostcat
Tomcat was found to be vulnerable to an unauthenticated LFI in a semi-recent discovery named Ghostcat. All Tomcat versions before 9.0.31, 8.5.51, and 7.0.100 were found vulnerable. This vulnerability was caused by a misconfiguration in the AJP protocol used by Tomcat. AJP stands for Apache Jserv Protocol, which is a binary protocol used to proxy requests. This is typically used in proxying requests to application servers behind the front-end web servers.
The AJP service is usually running at port 8009 on a Tomcat server. This can be checked with a targeted Nmap scan.
The above scan confirms that ports 8080 and 8009 are open. The PoC code for the vulnerability can be found here.
The exploit can only read files and folders within the web apps folder, which means that files like /etc/passwd can’t be accessed.
In some Tomcat installs, we may be able to access sensitive data within the WEB-INF file.
Credits: academy.hackthebox.com
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