A practical how-to on generating a targeted wordlist using Cuppy for smarter password cracking.
Back when I was helping a grassroots NGO secure their internal Wi-Fi, we kept hitting a wall. The problem wasn’t the router—it was the people. Volunteers reused birthdays, pet names, and “123456” like clockwork. Telling them to “use stronger passwords” didn’t cut it.
That’s when I turned to password cracking—not to break in, but to show them just how easy it was to guess their credentials. I needed a tool that could simulate real-world guessing with scary accuracy.
Enter Cuppy, a FOSS-powered, personalized wordlist generator that profiles human habits better than most people do.
In this guide, I’ll show you how to ethically use Cuppy in Termux to generate custom wordlists for password cracking exercises. Whether you’re a student of cybersecurity or helping secure a community network, this one’s for you.
Let’s get human with our hacking—read on.
⚠️ Important: These tools are intended for ethical hacking, security research, and education. Use them only on systems and networks you own or have permission to test. Unauthorized use can lead to serious legal consequences.
Download my FREE Hydra Cheat Sheet Now!
Meet Cuppy: The Wordlist Profiler
Cuppy (Common User Passwords Profiler) is a Python tool that builds targeted password lists based on what we know about a specific person — names, birthdays, relationships, hobbies, and more.
Think of it as Crunch’s more cunning cousin.
Where Crunch generates rules, Cuppy generates insight — it predicts the kind of passwords a real human might create. And as anyone who’s tested weak logins knows: humans are creatures of habit.
Let me show you how I used Cuppy to build a disturbingly accurate password list using only publicly available info.
Getting Started with Cuppy: Set the Stage for Smarter Password Cracking
Before you can crack passwords like a digital detective, you’ll need to set up the right environment. Cuppy isn’t just another script—it’s a clever little tool that turns personal info into potential passwords, giving you a real-world edge in ethical password cracking scenarios. But like most great tools in the FOSS ecosystem, it works best when properly installed and understood.
In this section, we’ll walk through getting Cuppy up and running inside Termux, your Android-based command line lab on the go. It’s lightweight, fast, and perfect for building human-centric wordlists anywhere, anytime.
Let’s prime your setup for action.
Set Up Termux (or Any Linux Terminal)
If you’re using Termux like I was:
pkg update && pkg upgrade
pkg install git pythonThen clone Cuppy:
git clone https://github.com/Mebus/cupp.git
cd cuppReady? Now it’s time to do a little profiling.
Go Interactive With Cuppy
Start Cuppy in interactive mode:
python3 cupp.py -iThis launches a series of prompts. I was building a list for a demo target — let’s call her Emz. She’s fictional, but the scenario? All too real.
Here’s how I filled it out:
[+] Insert the information about the victim to make a dictionary
[+] Name: Emz
[+] Surname: Reyes
[+] Nickname: Em
[+] Birthdate (DDMMYYYY): 05122000
[+] Partner's name: Jay
[+] Partner's nickname: Jayjay
[+] Partner's birthdate (DDMMYYYY): 17031998
[+] Child's name: —
[+] Pet's name: Mochi
[+] Company name: DevDigest
[+] Do you want to add some key words? [Y/n] Y
[+] Write the words separated by comma: wifi,1234,passwordCuppy crunched through the data and spit out:
[+] Wordlist Emz.txt created with 4312 words.And wow — some of the combinations hit way too close to home.
Inspect and Use the Wordlist
The resulting file lives in the same directory:
ls Emz.txtYou can check its contents like this:
cat Emz.txt | lesssam_06615
sam_0661980
sam_0665
sam_06680
sam_066980
sam_0680
sam_068015
sam_06805
sam_06806
sam_0680980
sam_06980
sam_0698015
sam_069805
sam_069806
sam_0698080
sam_15
sam_1506
sam_15065
sam_15066
sam_150680
sam_1506980
sam_151980
sam_1519805
sam_1519806
sam_155
sam_15506
sam_1551980Or combine it with other wordlists:
cat Emz.txt rockyou.txt | sort | uniq > merged-list.txtIf you’re using a tool like Hydra:
hydra -l emz.reyes -P Emz.txt ftp://192.168.1.100Boom. Human-like guesses delivered by your machine.
Why This Matters
Unlike brute-force or dictionary attacks that throw the kitchen sink at a login prompt, targeted wordlists cut through the noise. They simulate what a real person might use as a password — and more often than not, that’s exactly what gets reused across services.
This isn’t just about being clever. It’s about being efficient, ethical, and responsible in your red teaming or testing efforts.
Why Cuppy Is a Game-Changer for Ethical Password Cracking
The real power of Cuppy is its realism. It makes password cracking more strategic and less wasteful.
You’re not trying every possible combination. You’re trying the most probable ones first.
It’s also a great reminder for your clients: if someone can build your password list from your Instagram bio and a little guessing… your security policy needs a rewrite.
· · ─ ·𖥸· ─ · ·
Ethical Use: Why Responsible Password Cracking Matters
Password cracking tools like Cuppy hold immense power—and with great power comes great responsibility. As ethical hackers and FOSS advocates, our goal isn’t to exploit vulnerabilities for personal gain or chaos but to illuminate weaknesses so they can be fixed.
Using password cracking techniques responsibly means always having explicit permission before testing any system or account. It’s about helping individuals and organizations understand how predictable human behavior—like using birthdays or pet names—can make their passwords vulnerable. By generating custom wordlists tailored to real-world data, we simulate what an attacker might try, but only to strengthen security.
Remember: Ethical password cracking is a tool for education, defense, and awareness—not offense. It’s the difference between being a locksmith who improves security and a thief who breaks in.
· · ─ ·𖥸· ─ · ·
Crunch vs. Cuppy: Choosing the Right Password Cracking Wordlist Generator
When it comes to generating custom wordlists for ethical password cracking, Crunch and Cuppy are two popular FOSS tools—but they serve different purposes and use cases.
Crunch is a powerful, flexible CLI tool designed for creating massive wordlists based on specified character sets, lengths, and patterns. It’s ideal when you need to generate exhaustive or highly customized lists from scratch, such as all possible combinations of characters within certain constraints. Crunch’s strength lies in its brute-force approach, giving you total control over wordlist size and complexity.
On the other hand, Cuppy (Common User Passwords Profiler) takes a more targeted and intelligent approach. Instead of blindly generating permutations, Cuppy builds personalized wordlists based on interactive profiling questions—like names, birthdays, hobbies, and locations. This approach helps ethical hackers craft realistic, high-probability password lists tailored to a specific individual or organization, often increasing cracking efficiency by focusing on relevant data.
In summary:
- Use Crunch when you want broad, systematic coverage or need to create large combinatorial wordlists.
- Choose Cuppy for smart, context-driven password cracking where you can leverage personal or environmental clues.
Together, these tools complement each other in the ethical hacker’s toolkit—Crunch for raw power, Cuppy for precision.
· · ─ ·𖥸· ─ · ·
Pro Tips
- Keep your Cuppy-generated lists small and relevant. 4,000–6,000 entries is the sweet spot.
- Don’t rely on it alone — combine it with Crunch, CeWL, and OSINT data for layered attacks.
- Cuppy doesn’t do silent automation — it’s meant to be interactive. If you need batch processing, consider a fork or write a wrapper script using
expect.
Smarter Wordlists, Safer Systems
Cuppy feels like cheating — because it uses the very things we overshare to guess our secrets. That’s also what makes it such a powerful tool in the right hands.
If you liked this guide, check out my Crunch article, and stay tuned — next up, we’re going hybrid: OSINT + LinkedIn scraping + CeWL.
Want the toolkit I used for this demo?
Subscribe to DevDigest and get the full recon pack — Cuppy config, wordlists, and more.
⚠️ Important: These tools are intended for ethical hacking, security research, and education. Use them only on systems and networks you own or have permission to test. Unauthorized use can lead to serious legal consequences.
Leave a Reply