Bug Bounty $100,000 Roadmap — 12-Month Plan

I had claude help me make a 12 month plan and I am going to do it. 2026 is already 25% over. I do not want to waste any more time. I also used some info from this post by Justin Gardner (@Rhynorater)

I will spend as much time on Bug Bounty as I possibly can starting this Thursday, 26th March 2026.

Profile: BS Cybersecurity | A+, Net+, Sec+, Pentest+, CySA+, ISC2 SSCP

Commitment: 40+ hours/week

Track: Web Application Hacking

Math

To hit $100k, you need roughly one of these scenarios:

• 10–15 high-severity bugs at $5k–$10k each
• 3–5 critical bugs at $15k–$30k each + a handful of mediums
• 50–80 medium bugs at $1k–$2k each

The plan below optimizes for the middle path: specialize fast, get your first bounties within 90 days, then compound skills to chase criticals.

Overview

Phase 1 — Months 1–2: Foundation (~350 hrs total)

JavaScript — 40 hours

Resource: javascript.info (free) — complete Parts 1 and 2

Focus on:

• DOM manipulation
• document.location, innerHTML, eval()
• Event listeners and fetch()
• How cookies work in JS
• postMessage and cross-origin communication

Practice: Open any website, open DevTools, read their JS files. Try to understand what data flows where.

DOM XSS, client-side logic flaws, and postMessage vulnerabilities are all high-payout and invisible if you can’t read JS.

Burp Suite Mastery — 30 hours

Resource: PortSwigger Web Security Academy (free) — Burp Suite-specific sections

Learn:

• Intruder, Repeater, Comparer, Decoder, Logger
• Match-and-replace rules
• Writing Burp extensions in Python (Montoya API)
• Setting up FoxyProxy
• Intercepting mobile apps with Burp

HTTP & Web Fundamentals — 20 hours

Learn:

• Every HTTP status code and what it means in a bug context
• CORS, SameSite cookies, CSP headers
• How OAuth 2.0 flows work at the protocol level

Practice: Use curl for everything — it forces you to understand what Burp is doing under the hood.

PortSwigger Academy Labs — Ongoing

Start these in week 1, run in parallel with everything else. Goal: 50 labs completed by end of month 2.

Priority order:

1. SQL injection
2. XSS (all three types)
3. CSRF
4. Access control
5. Authentication

Phase 1 Goals (by day 60)

• Solve 50 PortSwigger labs
• Read JS well enough to spot sources and sinks
• Write a basic XSS payload from scratch without looking it up
• Understand every HTTP verb and common header
• Set up a full local Burp proxy environment

Phase 2 — Months 3–4: Core Vulnerability Classes (~350 hrs)

Now you start hunting for real, alongside learning.

IDOR & Broken Access Control — 25 hours

This is the #1 source of first bounties for new hunters. Companies consistently miss these because they require understanding business logic, not just technical scanning.

What to do:

• Every time you see a numeric ID in a URL or request body, try changing it
• Look for UUIDs — people think they’re secure by obscurity; they’re not if leaked elsewhere
• Test horizontal and vertical privilege escalation separately

Resources:

• The “IDOR Bible” write-up by @r0x
• Every HackerOne disclosed IDOR report (filter by “Broken Access Control” on HackerOne Hacktivity)

XSS Deep Dive — 25 hours

Go beyond <script>alert(1)</script>.

Learn:

• Stored XSS in rich text editors, file uploads, profile fields
• DOM XSS via location.hash, document.referrer, window.name
• Filter bypass techniques — encoding, polyglots, SVG payloads, mutation XSS (mXSS)
• How to use XSS Hunter to prove impact to triagers (this affects payout)

Resource: PortSwigger XSS labs — complete all of them including expert-level

SQLi, SSRF, XXE — 25 hours

SQL Injection:

• Focus on blind and time-based — these are still found in the wild constantly
• Learn sqlmap but understand what it’s doing under the hood

SSRF (Server-Side Request Forgery):

• This is a high-payout vulnerability. Learn cloud metadata endpoints (169.254.169.254)
• How to pivot SSRF to internal services
• Blind SSRF via out-of-band (use Burp Collaborator or interactsh)

XXE:

• File disclosure via external entity
• Blind XXE via OOB

Resource: PortSwigger labs for all three categories

Auth & Session Attacks — 15 hours

Learn:

• Password reset flow flaws (host header injection, token predictability, race conditions)
• Session fixation and session puzzling
• 2FA bypass techniques (code reuse, response manipulation, backup code flaws)

Resource: PortSwigger Authentication labs

Start Hunting in Month 3

Sign up for HackerOne and Bugcrowd. Start with programs that have “safe harbor” language and wide scope.

Good starting programs:

• HackerOne’s own bug bounty program
• U.S. Department of Defense VDP (great for learning, lower competition)
• Large tech companies with broad scopes and fast triage

Your goal in month 3 is not money — it is getting your first report triaged, even if it comes back as N/A. The feedback is invaluable.

Phase 2 Goals (by day 120)

• Submit first bug report (even if N/A)
• Win first bounty (aim: $100–$500)
• Complete HackTheBox or TryHackMe web labs
• Build a personal recon methodology document
• Read 20 disclosed reports on HackerOne Hacktivity
• Set up a notes system (Obsidian or Notion) for your findings

Phase 3 — Months 5–7: Advanced Techniques & Chaining (~420 hrs)

Business Logic Flaws — 30 hours

These cannot be found by scanners. They require understanding what the app is supposed to do and figuring out how to make it do something it should not.

Examples:

• Price manipulation and coupon stacking
• Quantity overflows and negative values
• Workflow bypasses (skipping steps in a multi-step process)
• Race conditions — two simultaneous requests that each independently pass a check

Resources:

• PortSwigger Business Logic labs
• Every disclosed “logic” bug on HackerOne Hacktivity

OAuth / JWT / SSO Attacks — 25 hours

These are disproportionately high payout because:

• They affect authentication, which is always critical impact
• They are complex enough that most junior hunters cannot find them
• Account takeover via OAuth is often a P1 ($10k+)

Learn:

• state parameter CSRF in OAuth flows
• Open redirect chaining to steal authorization codes
• Token leakage via referrer header
• JWT alg:none attack
• JWT secret brute-forcing with hashcat
• Implicit flow vulnerabilities

Resources:

• PortSwigger OAuth labs (all of them)
• “An Illustrated Guide to OAuth and OpenID Connect” (okta.com)

API Hacking — 25 hours

Every app has an API. Many are poorly documented and undertested.

Learn:

• Mass assignment vulnerabilities (sending extra JSON fields the API accepts)
• Excessive data exposure (API returns more data than the UI shows)
• Broken Object Level Authorization (BOLA — essentially API-level IDOR)
• Using Postman and REST Client to interact with APIs manually

Resources:

• OWASP API Security Top 10
• APIsec University (free)

GraphQL & WebSockets — 15 hours

GraphQL:

• Introspection queries to map the entire API surface
• Batch queries to bypass rate limiting
• GraphQL injection

WebSockets:

• Message tampering via Burp
• Cross-site WebSocket hijacking

Resource: PortSwigger GraphQL labs

Bug Chaining — 20 hours

This is the skill that 10x’s your payouts. A medium-severity XSS combined with an information disclosure that leaks an admin token equals a critical account takeover.

Practice:

• Every time you find a low-severity bug, ask: “what can I do with this?”
• Study how top hunters chain bugs in their public write-ups

Resource: https://pentester.land/list-of-bug-bounty-writeups — filter for “chain” write-ups

Build Your Recon Automation Pipeline

Set this up and let it run in the background while you manually test.

# Basic recon pipeline
subfinder -d target.com | httpx -silent | nuclei -t nuclei-templates/

# Passive URL collection
echo target.com | gau | grep "?" | tee urls.txt
cat urls.txt | waybackurls >> urls.txt

# GitHub dorking
# Search: org:targetorg password OR secret OR api_key

Tools to install:

• subfinder — subdomain enumeration
• amass — in-depth DNS enumeration
• httpx — HTTP probing
• nuclei — template-based scanning
• ffuf — fast web fuzzer
• gau — get all URLs
• waybackurls — Wayback Machine URL fetcher
• notify — send alerts to Telegram or Discord

Phase 3 Goals (by day 210)

• $5k–$15k earned total
• 1–2 programs you know deeply (understand their tech stack and past findings)
• Land first high-severity (P2) report
• Automated recon pipeline running
• Writing reports that get triaged without back-and-forth
• Receive first private program invite

Phase 4 — Months 8–12: Full Hunter Mode

By now you have a niche, a methodology, and repeating income. The job now is volume combined with depth.

Weekly Time Split

• 30 hours/week actively hunting on programs
• 10 hours/week learning new techniques and reading write-ups

Pick One Niche to Go Expert-Level

The hunters who make $100k+ are known for something. Choose based on where you have found the most success:

Private Programs

• HackerOne and Bugcrowd invite top hunters to private programs
• Private programs have less competition, higher payouts, and broader scope
• You get invites by: finding bugs, building reputation, and sometimes by directly asking program managers
• Target: First private invite by month 6–7

Report Quality

A well-written report gets triaged faster, bounty paid sooner, and triagers remember you for future reports.

Every report must include:

1. Vulnerability summary — one clear sentence describing the issue
2. Steps to reproduce — numbered, explicit, anyone should be able to follow them
3. Proof of concept — working exploit code, screenshots, or video walkthrough
4. Impact statement — what can an attacker actually do with this? Be specific
5. Suggested remediation — shows professionalism, speeds up triage

Phase 4 Goals (by month 12)

• $85k–$100k+ earned total
• Strong reputation score on HackerOne or Bugcrowd
• 3+ active private program invites
• At least one critical / P1 bug in your portfolio
• Recognized niche specialization
• Public write-up or conference talk (optional but accelerates invites)

Weekly Schedule

Platforms

Learning Resources

Free

• PortSwigger Web Security Academy — the single best resource on the internet for web hacking
• The Bug Hunter’s Methodology — Jason Haddix on YouTube, must-watch
• Nahamsec on YouTube/Twitch — one of the best hunters actively teaching
• PentesterLand write-ups list — https://pentester.land/list-of-bug-bounty-writeups
• HackerOne Hacktivity — disclosed reports, sorted by bounty amount

Tools Reference

Essential Setup

# Install Go (required for most tools)
sudo pacman -S go

# Recon tools
go install -v github.com/projectdiscovery/subfinder/v2/cmd/subfinder@latest
go install -v github.com/projectdiscovery/httpx/cmd/httpx@latest
go install -v github.com/projectdiscovery/nuclei/v3/cmd/nuclei@latest
go install -v github.com/ffuf/ffuf/v2@latest
go install -v github.com/lc/gau/v2/cmd/gau@latest
go install -v github.com/tomnomnom/waybackurls@latest

# Update nuclei templates
nuclei -update-templates

Burp Suite Extensions to Install

• Autorize — automatic access control testing
• Turbo Intruder — fast fuzzing beyond what Intruder can do
• Logger++ — advanced request logging
• JS Miner — extracts endpoints and secrets from JS files
• Param Miner — discovers hidden parameters

Key Mindset Points

The first 60 days are the hardest.

Read more write-ups than you think you need to. The fastest way to learn to find bugs is to understand exactly how other people found them. Aim for 5 write-ups per day in months 1–4.

Go deep on programs, not wide.

Impact is everything. A bug is only worth what an attacker can do with it. Always ask: “can I chain this into something worse?” A self-XSS is N/A. A self-XSS that becomes account takeover via a CSRF is a P2.

Your reports are your reputation.

Last updated: March 2026