After empirical testing on Security Shepherd v3:
Username: admin
Password: ' = '
Query becomes:
WHERE username='admin' AND password='' = ''
Since '' = '' is true, the condition reduces to username='admin', allowing login.
Then, to extract flag (assuming you have a second injection point after login), you use a vulnerable parameter in the logged-in area.
But Challenge 5 stops at login success. The flag is returned upon successful admin login.
Thus, final answer for the challenge:
Flag: Retrieved automatically after logging in with admin and password ' = '.
Doing this manually for 32 characters is intellectually satisfying but practically insane. The intended solution for Challenge 5 is a script. Below is a Python example using requests to automate Boolean blind SQL injection.
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.
To perform a UNION SELECT, your injected query must have the same number of columns as the original query. We need to find this number.
Try injecting the following payloads to test for column count using the ORDER BY technique:
Payload 1:
' ORDER BY 1--
(If no error, there is at least 1 column) Sql Injection Challenge 5 Security Shepherd
Payload 2:
' ORDER BY 2--
(If no error, there are at least 2 columns)
Payload 3:
' ORDER BY 3--
(If no error, there are at least 3 columns)
Payload 4:
' ORDER BY 4--
If the application returns an error (or a blank page) at ORDER BY 4, but worked for ORDER BY 3, then the original query has 3 columns.
Author: Security Researcher
Date: April 11, 2026
Subject: Web Application Security / SQL Injection (Level: Intermediate)
If you are using this article for defensive training, here is how to prevent Challenge 5 from existing in your own code: After empirical testing on Security Shepherd v3: Username:
To switch from Blind to Union-based injection, we need to know how many columns the original SELECT statement returns. We use ORDER BY for this.
Payload sequence:
1 ORDER BY 1 -- -
1 ORDER BY 2 -- -
1 ORDER BY 3 -- -
Continue until the page breaks (returns empty or error). If it breaks at ORDER BY 5, the column count is 4.
Pro tip: If ORDER BY is filtered, use 1 GROUP BY 3,2,1 to test column counts.
For Challenge 5, the magic number is often 3 or 4 columns.
Navigate to the challenge. You will see a generic submission field. The most common vector in this challenge is the "Account Name" or "Username" field. Continue until the page breaks (returns empty or error)
Try entering a generic input like:
test
If the application returns "Your account name is test", you have confirmed the application is reflecting input back to you. This is crucial for a UNION-based injection.