🔐 Can you crack this modern KeePass 4.x encrypted vault using advanced techniques?

KeePass 4.x databases (KDBX 4.x format) use strong encryption (AES-256 or ChaCha20) with key derivation functions like Argon2. Important: Traditional tools like keepass2john do not support KDBX 4.x format yet, so hash extraction methods used for older KeePass versions will not work. Direct brute force against the database file is required.

1. Download the database: Download the challenge_vault.kdbx file from the challenge page
2. Verify the format: Confirm this is a KeePass KDBX 4.x format file
3. Install tools: Set up tools for KeePass 4.x brute forcing

# Install KeePassXC CLI
sudo apt-get install keepassxc

# Or install Python KeePass library
pip3 install pykeepass

# File verification
file challenge_vault.kdbx

Method 1: Using keepass4brute Tool

1. Install keepass4brute: Clone the specialized tool for KDBX 4.x

# Clone keepass4brute tool
git clone https://github.com/r3nt0n/keepass4brute.git
cd keepass4brute

# Make executable
chmod +x keepass4brute.sh

2. Create efficient wordlists: Use high-probability, small wordlists for faster cracking

# Install SecLists (comprehensive security wordlists)
git clone --depth 1 https://github.com/danielmiessler/SecLists.git

# Use most effective small wordlists for KeePass cracking:
# Top 207 most probable passwords (very fast)
cp SecLists/Passwords/Common-Credentials/probable-v2-top207.txt .

# Top 100 passwords from dark web breaches (fast)
cp SecLists/Passwords/darkweb2017-top100.txt .

# Top 200 most used passwords from 2023 (fast)
cp SecLists/Passwords/2023-200_most_used_passwords.txt .

# Create simple test wordlist
echo -e "password\nadmin\nqwertyuiop\n123456\npassword123" > quick_test.txt

3. Run the brute force attack with efficient wordlists:

# Start with quick test (5 passwords)
./keepass4brute.sh ../challenge_vault.kdbx quick_test.txt

# Try top 207 most probable passwords (fast)
./keepass4brute.sh ../challenge_vault.kdbx probable-v2-top207.txt

# Try dark web top 100 (if not found)
./keepass4brute.sh ../challenge_vault.kdbx darkweb2017-top100.txt

# Try 2023 top 200 passwords (if still not found)
./keepass4brute.sh ../challenge_vault.kdbx 2023-200_most_used_passwords.txt

4. Success result: The password is found to be qwertyuiop

Method 2: Python-based Direct Brute Force

1. Python script approach: Test passwords directly against the database

#!/usr/bin/env python3
from pykeepass import PyKeePass

def crack_keepass(db_path, wordlist_path):
    with open(wordlist_path, 'r') as f:
        for password in f:
            password = password.strip()
            try:
                kp = PyKeePass(db_path, password=password)
                print(f"Password found: {password}")
                return password
            except:
                continue
    return None

# Test common passwords
common_passwords = ['password', 'admin', 'qwertyuiop', '123456']
for pwd in common_passwords:
    try:
        kp = PyKeePass('challenge_vault.kdbx', password=pwd)
        print(f"Password found: {pwd}")
        break
    except:
        continue

2. Run the script:

python3 crack_keepass.py

Method 3: Manual Password Testing

1. Test passwords manually: Use KeePassXC command-line interface

# Test individual passwords by listing entries
keepassxc-cli ls challenge_vault.kdbx
# Enter password when prompted: qwertyuiop

# Or test specific password non-interactively
echo "qwertyuiop" | keepassxc-cli ls challenge_vault.kdbx

2. Bash script for automation:

#!/bin/bash
wordlist=("password" "admin" "qwertyuiop" "123456")
for pwd in "${wordlist[@]}"; do
    echo "Testing: $pwd"
    if echo "$pwd" | keepassxc-cli ls challenge_vault.kdbx &>/dev/null; then
        echo "Password found: $pwd"
        break
    fi
done

1. Open with KeePassXC: Use the cracked password qwertyuiop to open the database
2. Using KeePassXC CLI:

# List groups in database
echo "qwertyuiop" | keepassxc-cli ls challenge_vault.kdbx

# List entries in the Confidential Documents group
echo "qwertyuiop" | keepassxc-cli ls challenge_vault.kdbx "Confidential Documents/"

# Show specific entry with protected fields revealed
echo "qwertyuiop" | keepassxc-cli show challenge_vault.kdbx "Confidential Documents/Flag" --show-protected

3. Using Python script:

#!/usr/bin/env python3
from pykeepass import PyKeePass

kp = PyKeePass('challenge_vault.kdbx', password='qwertyuiop')

# Find all entries
for entry in kp.entries:
    print(f"Title: {entry.title}")
    print(f"Username: {entry.username}")
    print(f"Password: {entry.password}")
    print("---")

4. Flag extraction: Look for the entry titled "Flag"

Why Traditional Tools Don't Work

• KDBX 4.x format: Newer format not supported by keepass2john
• Enhanced security: Stronger key derivation functions (Argon2)
• No hash extraction: Cannot extract hashes for offline cracking

Direct Attack Strategies

• keepass4brute: Specialized tool for KDBX 4.x brute forcing
• Python libraries: Direct database access with pykeepass
• Native tools: KeePassXC CLI for manual testing

Wordlist Optimization Strategy

• Start small: Begin with high-probability, small wordlists (207-200 passwords)
• SecLists efficiency: Use curated lists like probable-v2-top207.txt and darkweb2017-top100.txt
• Progressive approach: Move to larger lists only if needed (rockyou.txt has 14M passwords)
• Speed matters: Direct KeePass attacks are slower than hash cracking, so efficiency is critical

Why This Attack Succeeded

• Weak password: 'qwertyuiop' is a keyboard pattern password that appears in common wordlists
• Predictable pattern: Simple keyboard pattern easily recognized by attackers
• No complexity: Lacks special characters and adequate length for strong protection

Prevention Strategies

• Strong master passwords: Use long, complex passwords with mixed characters
• Passphrases: Consider multi-word passphrases for better security
• Key files: Use combination of password + key file for two-factor authentication
• Regular audits: Test password strength against modern cracking tools

• keepass4brute: Specialized tool for KDBX 4.x brute force attacks
• PyKeePass: Python library for KeePass database manipulation and testing
• KeePassXC-CLI: Command-line interface for KeePass database access
• SecLists: Comprehensive security wordlist collection with optimized password lists
• Custom scripts: Python/Bash automation for password testing

This KeePass Breaker challenge demonstrates the evolving landscape of password manager security. While KeePass 4.x provides enhanced protection against traditional hash-based attacks, weak master passwords remain the critical vulnerability. The challenge emphasizes the need for strong password policies, modern assessment techniques, and understanding of current tool limitations when evaluating password manager security.