SQL Injection Challenge 5 from Security Shepherd is a web-app training exercise that demonstrates a common but subtle SQL injection pattern: blind inference attacks against application logic that uses dynamic queries and insufficient input handling. The goal of this write-up is to explain the challenge’s likely design, the vulnerability class it teaches, the exploitation methodology, and remediation strategies developers can apply.
Now that we know there are 3 columns, we can craft a payload to extract data from the database schema. We want to find the password column for the admin user.
SQL Injection Challenge 5 in OWASP Security Shepherd is a rite of passage. It strips away the crutches of error messages and visible output, forcing you to rely on the most fundamental atomic unit of information: a binary choice.
By mastering this challenge, you prove you can:
More importantly, you internalize a crucial truth of security: Even a single bit of leaked information—true or false—can be weaponized to reconstruct an entire database. Whether you are a blue teamer fixing vulnerabilities or a red teamer testing defenses, the lessons of Challenge 5 will serve you on every engagement.
Now, go launch Security Shepherd, navigate to Challenge 5, and watch that script extract the key. Then, ask yourself: Is my own application leaking Boolean oracles like this?
Further Resources:
Disclaimer: This article is for educational purposes only. Only test SQL injection on systems you own or have explicit permission to test.
OWASP Security Shepherd SQL Injection Challenge 5 requires bypassing single-quote filtering by injecting a backslash, resulting in a payload like \' OR 1=1; -- . This technique unescapes the quote, allowing for an
statement to reveal the VIP Coupon Code. For a detailed breakdown of this solution, visit Security Stack Exchange couponcode from challenges SQL injection 5 #323 - GitHub Sql Injection Challenge 5 Security Shepherd
OWASP Security Shepherd's SQL Injection Challenge 5, or "VIP Coupon Check," demonstrates how unsanitized input concatenated directly into database queries creates critical SQL injection vulnerabilities. Attackers can bypass input validation using ' OR '1'='1 or utilize UNION SELECT statements to extract hidden data from the backend. For a detailed walkthrough of this specific challenge, visit this Numerade article. SqlInjection5VipCheck.java - GitHub
OWASP Security Shepherd's SQL Injection Challenge 5 focuses on Boolean-based Blind SQL Injection, requiring users to extract hidden data by inputting TRUE/FALSE queries to infer information. Attackers exploit this by analyzing application responses to guess characters one-by-one using SQL functions like SUBSTRING()
You're referring to the SQL Injection Challenge 5 on Security Shepherd!
For those who may not know, Security Shepherd is a free online platform that provides a series of challenges to help developers and security professionals learn about common web application vulnerabilities, including SQL injection.
Now, let's dive into Challenge 5!
Challenge 5: SQL Injection - Extract Data (Time-Based Blind)
In this challenge, you'll encounter a web application that is vulnerable to SQL injection. Your goal is to extract data from the database using time-based blind SQL injection techniques.
The Challenge:
You are presented with a simple search form that allows you to search for users by their username. The application uses a SQL database to store user information. Your task is to inject malicious SQL code to extract data from the database. SQL Injection Challenge 5 from Security Shepherd is
The Query:
The application uses the following SQL query to search for users:
SELECT * FROM users WHERE username = '$searchTerm' AND password = '$password';
Your Goal:
Use time-based blind SQL injection techniques to extract the username and password of at least one user from the database.
Tips and Hints:
Example Payload:
Here's an example payload to get you started:
' OR IF(MID(VERSION(),1,1)='5',SLEEP(5),1) --
This payload injects a conditional statement that checks the version of the database. If the version starts with '5', the query will sleep for 5 seconds.
What do you need to do?
This script solves Challenge 5 in seconds. But understanding why it works is what makes you a security professional.
With visible injection points (e.g., column positions 2 and 3), we query the information_schema database—the MySQL system catalog.
Payload to list tables:
1 AND 1=2 UNION SELECT 1,table_name,3 FROM information_schema.tables WHERE table_schema=database() -- -
Note: In Security Shepherd, you often need to URL-encode spaces and special characters. The -- - (space, hyphen, hyphen, space) terminates the query cleanly.
What you’re looking for: A table named users, administrators, or shepherd_users.
OWASP Security Shepherd SQL Injection Challenge 5 is a hands-on exercise designed to teach advanced exploitation techniques by using sub-query injection to bypass input filters and extract a hidden VIP coupon code. The challenge, often featuring a "Troll Shop" scenario, requires using UNION SELECT techniques to map backend table structures and retrieve secure data. For more details, visit GitHub. couponcode from challenges SQL injection 5 #323 - GitHub
Search for:
Example known write-ups:
If you want, I can write a short technical paper in that style for Challenge 5, including a blind SQL injection script. Would that help? More importantly, you internalize a crucial truth of
The login logic likely follows a pattern (pseudocode):
SELECT user_id FROM users
WHERE username = '<input_user>'
AND password = '<input_pass>'
If the query returns a row, login succeeds.