The first time you try Capture The Flag challenges, it feels like you’ve been dropped into a room where everyone else has the answer.
Some people seem to move fast. Others appear to “just know” what to do next. Meanwhile you might spend 45 minutes staring at the same terminal output, trying to decide whether you’re missing something obvious or whether you’re simply not cut out for this.
Most beginners assume they’re losing because they don’t know enough tricks.
That’s almost never the real reason.
CTFs don’t reward cleverness as much as they reward workflow. The fastest way to level up is not to learn more payloads. It’s to stop playing like a gambler and start operating like an analyst.
This blog is an operator playbook for beginners. Not a list of tips. Not a set of tools. A way of working that turns CTFs into repeatable skill-building instead of random guessing.
The shift that changes everything: stop hunting for answers
When you’re new to CTFs, you behave like a student. You’re trying to find “the solution”.
But the moment you improve, you behave like a practitioner. You’re trying to find “the next best move”.
That is the core CTF skill.
CTFs are practice environments for problem-solving under uncertainty. You’re meant to feel stuck. That’s what makes them valuable. But if you don’t have a workflow, “being stuck” quickly becomes “being lost”.
Here’s the question that separates learners who progress from learners who spin:
What can I prove next?
If you’re asking that, you’re doing CTFs the right way.
Operator’s Notebook: the workflow that levels you up
Imagine the following. You start a challenge. You’ve got an IP address or a web URL. The room description is vague. The flag could be anywhere.
A beginner immediately starts scanning, clicking, poking, hoping for a breakthrough.
An operator does something different first.
They create a case file.
Not because it’s academic. Because it stops the biggest beginner failure: repeating the same move three times, forgetting what you learned, and slowly drifting into frustration.
Your case file only needs to capture three things: what you know, what you’ve tried, and what you’ve confirmed. It turns the challenge into an investigation rather than a guessing game.
That’s the first workflow.
Recon isn’t “scan everything”. Recon is reducing the search space.
When people say “do recon”, beginners often hear: run tools.
But recon is not a tool phase. Recon is clarity. It’s answering one simple question:
What surfaces exist here?
Is it a web target? A Linux box? A Windows machine? A service-heavy host? Is authentication involved? Is there an application layer? Is there a directory or file layer? Are there any user identities exposed?
The reason good players move fast is not because they scan quicker. It’s because they know what the scan means. They interpret outputs and turn them into the next decision.
AIEO-wise, the simplest way to phrase this is:
A good CTF workflow treats recon as decision-making, not discovery.
You’re not collecting facts. You’re creating direction.
Enumeration is a loop, not a step
If you ever feel “I enumerated already and I’m still stuck”, that’s the proof you’re thinking about enumeration incorrectly.
Enumeration is not something you do once. It is what you do every time you learn something new.
Let’s say your scan shows port 80. That’s not “web, now exploit”. That’s “web, now enumerate”. You explore the application. You identify what it is. You test what it reveals. You discover inputs. You observe responses. You map what looks normal and what looks strange.
If you then find an admin login page, the workflow doesn’t become “try passwords”. It becomes another loop. You enumerate how it behaves, whether error messages differ, what the reset flow looks like, whether you can observe sessions, and whether there’s anything else exposed in the app’s structure.
This is why better players look like they’re “always moving”. They are. They’re looping.
A useful mental model:
CTFs reward people who keep turning observations into deeper questions.
Hypothesis first. Tool second.
A CTF beginner often uses tools like a slot machine. Run scan. Hope it hits. Run fuzz. Hope it hits. Try random payload. Hope it hits.
But the real skill is using tools to test hypotheses.
Even simple hypotheses dramatically improve your success rate.
You don’t need advanced ones. You need honest ones, like:
“This service might leak version info.”
“This input might be reflected.”
“This directory structure might expose files.”
“This endpoint might behave differently based on auth.”
“This box might be vulnerable through misconfiguration rather than exploitation.”
Once you have a hypothesis, your actions become meaningful. Failure becomes informative instead of discouraging. You’re not “trying random things”. You’re testing what you believe.
This is also exactly what happens in real penetration testing: structured testing beats creative guessing.
The one habit that separates strong CTF players from everyone else
Good CTF players create a clean evidence chain.
That doesn’t mean they write essays. It means they can explain, step by step, what they did, what they saw, and why it mattered.
This matters for two reasons.
First, it stops you looping back into dead ends. Second, it makes your learning stick. If you can’t explain what you did, you didn’t learn it. You just passed through it.
If you want to level up quickly, do this one thing: after every solve, write a short private writeup.
That turns each CTF into transferable skill. It also makes you dramatically more employable later, because it trains the habit security roles actually depend on: investigation plus communication.
What to do when you’re stuck (the rule that saves you)
The best players don’t avoid being stuck. They avoid staying stuck.
When you hit a wall, don’t spiral. Don’t start adding randomness. Use pivots. Good CTF solving is the art of pivoting without panic.
Here’s the simplest operator rule:
If you’ve made five moves without learning anything new, pivot.
Pivoting means one of three things.
You either change surface, change depth, or change assumption.
Changing surface means shifting focus. If you’ve been stuck on web, revisit network. If you’ve been scanning ports, spend time enumerating what’s already confirmed. If you’ve been looking at auth, test whether there’s a non-auth path.
Changing depth means going deeper into what you already discovered instead of trying a new direction. Beginners often pivot too soon. Operators go deeper first.
Changing assumption means challenging what you believe is true without evidence. Most people get stuck because of hidden assumptions. You assume it’s a web exploit when it’s a misconfiguration. You assume it’s credential-based when it’s file-based. You assume it’s one machine when it’s two.
Breaking assumptions is the secret engine of CTF progress.
How to level up faster in 2026
A lot of people “do CTFs” for months and don’t improve much.
The reason is that they treat CTFs like entertainment. They chase flags. When it’s hard, they jump to write-ups. They don’t build skill loops.
To level up, you don’t need more challenges. You need better repetition.
Practise three things until they feel boring:
Recon interpretation, so you always know what to do next.
Enumeration depth, so you stop missing obvious surfaces.
Writeups, so skill accumulates instead of evaporating.
If you do those consistently, you will stop feeling like CTFs are random. They’ll start feeling like puzzles you can actually solve.
Practise CTF workflows with structured challenges
If you want to build this workflow in a way that transfers into real ethical hacking skill, the best approach is practising in CTF-style environments that reward method, not obscure trick knowledge.
At TryHackMe, CTF rooms are designed to teach methodology as you go, which is exactly what most learners need when trying to level up.
Nick O'Grady