My First Bug Bounty: Lessons Learned

Breaking into bug bounty hunting can be intimidating. The field seems dominated by experienced researchers with decades of security expertise, making it challenging for newcomers to find their footing. Here's my journey from zero to my first successful submission and the valuable lessons I learned along the way.

The Beginning: Where I Started

Like many aspiring bug hunters, I started with basic knowledge of web applications and a burning curiosity about security. My background was primarily in software development, which gave me some understanding of how applications work, but security was largely uncharted territory.

My first few months were spent learning the fundamentals through various resources:

• OWASP Top 10: Understanding the most common vulnerability types
• Web Security Academy: PortSwigger's excellent free training platform
• Bug Bounty Bootcamp: Vickie Li's comprehensive guide
• YouTube Channels: Following researchers like NahamSec, STÖK, and InsiderPhD

Setting Up My Testing Environment

Before diving into real targets, I invested time in setting up a proper testing environment:

Essential Tools

• Burp Suite: My primary web application testing tool
• OWASP ZAP: Free alternative for automated scanning
• Firefox with security extensions: FoxyProxy, Wappalyzer, etc.
• Command line tools: nmap, sqlmap, gobuster, and more

# Essential command-line tools setup
# Install gobuster for directory brute forcing
go install github.com/OJ/gobuster/v3@latest

# Install ffuf for web fuzzing  
go install github.com/ffuf/ffuf@latest

# Install nuclei for vulnerability scanning
go install -v github.com/projectdiscovery/nuclei/v2/cmd/nuclei@latest

# Install waybackurls for historical URL discovery
go install github.com/tomnomnom/waybackurls@latest

Practice Makes Perfect

Before attempting real bug bounties, I spent considerable time on practice platforms:

Learning Platforms

• PortSwigger Web Security Academy: Comprehensive labs covering all major vulnerability types
• HackTheBox: Hands-on penetration testing practice
• TryHackMe: Beginner-friendly security challenges
• DVWA: Deliberately vulnerable web application for local testing

These platforms taught me not just how to find vulnerabilities, but how to think like both an attacker and a defender.

The First Attempt: Reality Check

My first real bug bounty attempt was... humbling. I chose a popular program on HackerOne, thinking bigger targets meant more opportunities. I was completely overwhelmed:

• The attack surface was massive and confusing
• I didn't know where to start or what to prioritize
• My methodology was chaotic and inefficient
• I found several false positives and wasted time on rabbit holes

After two weeks of frustration with no valid findings, I realized I needed a more structured approach.

Developing a Methodology

My breakthrough came when I developed a systematic methodology:

1. Reconnaissance Phase

# Subdomain enumeration
subfinder -d target.com -silent | httpx -silent -mc 200 | tee subdomains.txt

# Technology detection
whatweb -a 3 target.com

# Wayback machine URL discovery
cat subdomains.txt | waybackurls | grep -E "\.(js|php|aspx|html)" | sort -u

2. Manual Testing Focus Areas

• Authentication and authorization flaws
• Input validation issues
• Business logic vulnerabilities
• Information disclosure

3. Documentation

I started keeping detailed notes of everything I tested, including negative results. This prevented me from repeating work and helped identify patterns.

The Discovery: My First Valid Bug

My first valid vulnerability was found on a smaller, less crowded program - an Insecure Direct Object Reference (IDOR) that allowed users to access other users' private documents.

The Vulnerability

The application had an endpoint for downloading user documents:

GET /api/documents/12345 HTTP/1.1
Host: target.com
Authorization: Bearer [user_token]

The vulnerability was simple but effective - changing the document ID in the URL allowed access to other users' documents:

# My document (legitimate access)
GET /api/documents/12345

# Other user's document (IDOR vulnerability)  
GET /api/documents/12346

The application failed to verify that the authenticated user had permission to access the requested document.

The Report: Getting It Right

Writing the vulnerability report was crucial. I learned that a good report should include:

Essential Elements

1. Clear Summary: Concise description of the vulnerability
2. Impact Assessment: What an attacker could achieve
3. Proof of Concept: Step-by-step reproduction
4. Evidence: Screenshots and request/response data
5. Remediation: Suggestions for fixing the issue

# Example Report Structure
**Summary:** Insecure Direct Object Reference in Document Download API

**Vulnerability Details:**
The /api/documents/{id} endpoint fails to verify user authorization...

**Impact:** 
Unauthorized access to sensitive user documents...

**Steps to Reproduce:**
1. Login as User A
2. Navigate to document download API
3. Change document ID parameter
4. Access User B's private documents

**Proof of Concept:**
[Screenshots and HTTP requests]

**Recommended Fix:**
Implement proper authorization checks...

The Response and Validation

The security team's response came within 48 hours - much faster than I expected. They confirmed the vulnerability and awarded a bounty of $500. While not a huge amount, the validation meant everything to me.

Key Lessons Learned

1. Start Simple

Don't overlook basic vulnerabilities. IDOR, broken access controls, and simple injection flaws are still common and valuable.

2. Choose Your Targets Wisely

Smaller, less crowded programs often provide better opportunities for newcomers. The competition is less intense, and security teams may be more responsive.

3. Be Patient and Persistent

Bug hunting requires significant time investment. My first valid bug came after months of learning and dozens of hours of testing.

4. Quality Over Quantity

One well-documented, valid vulnerability report is worth more than multiple poor-quality submissions.

5. Keep Learning

The security landscape evolves constantly. Successful bug hunters are continuous learners who adapt to new technologies and attack vectors.

6. Build a Methodology

Systematic approaches are more effective than random testing. Develop checklists and workflows that ensure comprehensive coverage.

7. Document Everything

Detailed notes prevent duplicate work and help you learn from both successes and failures.

Building on Success

My first bug bounty success opened several doors:

• Increased confidence to tackle more complex targets
• Recognition within the bug bounty community
• Invitations to private programs
• Networking opportunities with other researchers

Common Pitfalls to Avoid

1. Duplicate Reports

Always search for existing reports or CVEs before submitting. Duplicates hurt your reputation.

2. Out-of-Scope Testing

Read and respect program scope carefully. Testing out-of-scope assets can get you banned.

3. Poor Communication

Be professional and clear in all communications. Avoid demanding immediate responses or being confrontational.

4. Inadequate Testing

Ensure your proof of concept actually works and demonstrates real impact.

Tools and Resources That Made a Difference

Learning Resources

• Books: "Web Application Hacker's Handbook" by Dafydd Stuttard
• Courses: Pentester Academy, eLearnSecurity
• Blogs: Following researchers' writeups and methodologies
• Twitter: Security community discussions and tool announcements

Automation Tools

# Essential automation tools I use regularly
nuclei -t /path/to/templates -u target.com
ffuf -u https://target.com/FUZZ -w wordlist.txt
gospider -s "https://target.com" -o output -c 10 -d 5

The Road Ahead

My first bug bounty was just the beginning. Since then, I've submitted dozens of reports, earned several thousand dollars in bounties, and most importantly, contributed to making the internet more secure.

The key is to start somewhere and keep learning. Every expert was once a beginner, and every successful bug hunter has stories of early failures and lessons learned the hard way.

Advice for Aspiring Bug Hunters

1. Set Realistic Expectations

Bug bounty hunting is competitive and time-consuming. Don't expect immediate success or life-changing payouts.

2. Focus on Learning

Prioritize knowledge and skill development over monetary rewards, especially in the beginning.

3. Join the Community

Engage with other researchers through Twitter, Discord, and local meetups. The community is generally helpful and supportive.

4. Stay Ethical

Always follow responsible disclosure practices and respect program guidelines.

5. Never Stop Learning

Security is a rapidly evolving field. Continuous learning is essential for long-term success.

Conclusion

My first bug bounty experience taught me that success in security research comes from persistence, systematic thinking, and continuous learning. While the journey can be challenging, it's incredibly rewarding both financially and professionally.

Remember, every expert was once a beginner. Your first bug bounty might not make you rich, but it will give you the confidence and experience to tackle more complex challenges. The most important step is getting started.