Huntress CTF: Beginner's Guide to the October CTF (2026)

What Is the Huntress CTF?

The Huntress CTF is an annual, Jeopardy-style online Capture the Flag competition hosted by Huntress during Cybersecurity Awareness Month. Challenges are released daily for the whole of October, and players or teams earn points by finding hidden flags in files, web apps, logs, and malware samples built to mimic real intrusions.

Huntress describes it on its official CTF page as "easy, free, and open to all," with more than 60 unique challenges in past events. The host is John Hammond, a principal security researcher at Huntress, whom many beginners already know from his YouTube walkthroughs.

The event has grown quickly. Huntress reported more than 7,000 players and 3,000 teams in 2024, then 11,898 registered users and 6,892 teams in 2025, according to its own retrospective posts.

Why it is worth a month of your evenings:

• It costs nothing. No fee, no VPN subscription, no hardware.
• It is built from real attacks. Huntress's 2024 retro is literally titled "Turning TTPs into CTF Challenges": challenges recreated MOVEit, ScreenConnect, and Pass the Hash intrusions the company had seen in the field.
• The daily drip suits busy people. One or two new challenges a day is a manageable after-work habit, unlike a 48-hour weekend sprint.
• It teaches blue team skills. Most CTFs reward breaking things. This one rewards understanding what an attacker already did, which is closer to an entry-level SOC job.

How the Huntress CTF Works

The basic rhythm has stayed the same since at least 2023: one month, daily releases, one scoreboard. Here is what the official pages say about the format.

Registration and teams

You create a personal account on the CTF platform, then create a team or join one. Registering early does not give you a head start: the 2026 event page states plainly that registration does not open challenges before the event begins. Since 2025 the CTF has run on CourseStack, which Huntress adopted when registrations passed 10,000.

Because team size is unlimited, you will see everything from solo players to large company and school teams. Do not let that scare you. Plenty of people play alone just to learn, and the scoreboard matters far less than the skills you pick up.

Dynamic scoring

Every challenge starts at a high value and drops as more people solve it. In 2024, the opening Calculator challenge was worth 500 points, and over six thousand people opened it on day one. The practical consequence: an easy challenge solved on release day and a hard one solved by few players can end up worth very different amounts, so do not panic if your score jumps around overnight.

What changed in 2026: AI Arena

The 2026 edition kept the October calendar but changed the interface. According to the event page, players used the "Huntress AI Arena Homebase" to reason through challenge systems, investigate evidence, and submit "dynamic completion tokens" for scoring, with new challenge modules opening every day at 9 AM Eastern. Huntress has not said whether the 2027 event will keep this format, so treat the classic flag-hunting skills below as the safe bet.

What Huntress CTF Challenges Look Like

The best way to know what is coming is to look at what already came. Challenges stay secret during the event, but Huntress and its players publish retrospectives and write-ups afterwards.

2023: a defensive mix

A detailed write-up series on the Baker Street Forensics blog counted 58 unique challenges in the 2023 edition, split like this:

• Malware: 16
• Warmups: 14
• Forensics: 10
• Miscellaneous: 10
• Microsoft 365: 4
• OSINT: 3
• Steganography: 1

Notice how little classic web or binary exploitation there is. Malware and forensics alone made up almost half of the board.

2024: real intrusions, recreated

Huntress counted more than 70 challenges in 2024. The retro names several that were rebuilt from incidents its SOC had handled: "MOVEable" (MOVEit Transfer exploitation), "HelpfulDesk" (a ScreenConnect vulnerability), "Zippy" (SysAid), and "Little Shop of Hashes," a recreated Pass the Hash intrusion. "Nightmare on Hunt Street" was pure log analysis, and the finale, "Palimpsest," was built around Windows event logs.

2025: deobfuscation everywhere

The 2025 retrospective is titled "Deobfuscating Files for Flags," and that sums it up. Examples it highlights:

• Sandy (day 3): decode Base64 inside a decompiled AutoIt script to reveal a crypto stealer.
• Lizard: peel apart nested PowerShell in an adware-style scenario.
• My Hawaii Vacation: deobfuscate a Lua-based infostealer.
• Follow the Money: an OSINT trail that starts from .eml email files.
• Root Canal: reverse engineer a Linux kernel rootkit, one of the hard ones.

The pattern across three years is clear. If you can decode layered encodings, read a script that was written to be unreadable, and pull a story out of logs and emails, you can score in the Huntress CTF.

Is the Huntress CTF Good for Beginners?

Yes, with a caveat. Huntress says it is open to everyone from beginners to experienced professionals, and the warmup category exists precisely for newcomers. The caveat is that the difficulty curve is steep: past editions quickly moved on to obfuscated malware, Windows event logs, and even a Linux kernel rootkit.

Here is what a realistic first Huntress CTF looks like:

1. Solve every warmup. They teach the platform, the flag format, and the habit of checking file types before guessing.
2. Pick one category and go deep. Forensics or OSINT is the friendliest choice for a first-timer. Malware is where most points live, but also where most beginners stall.
3. Read the write-ups in November. The challenges you could not solve are the most valuable part of the event, once someone shows you the trick.

In practice, the beginners who get the most out of it are the ones who show up daily. Opening each new challenge on release day, even if you only spend 30 minutes on it, beats binge-playing the last weekend when everything is worth fewer points and you are trying to learn ten techniques at once.

How to Prepare for the Huntress CTF

You do not need to become a malware analyst before October. You need a safe workspace, four or five tools you can use without looking up the syntax, and the reflex to ask "what is this file, really?"

Build a safe lab first

A free hypervisor like VirtualBox with a Linux VM (Kali or REMnux) covers most challenges. A Windows VM helps for the PowerShell and Windows event log tasks, since some tools are easier to run there.

The core toolkit

• CyberChef: the browser "kitchen" for Base64, hex, XOR, gzip, and every combination of them. It is where almost every deobfuscation challenge starts.
• The file and strings commands: the first two commands to run on any unknown file. They tell you what it is and what readable text it hides.
• A good text editor and Python: for de-tangling scripts and writing the small decoder you will need at 11 PM on day 17.
• Wireshark and a log tool: Wireshark for packet captures, and grep or Eric Zimmerman's free tools for Windows event logs.
• Ghidra: for the compiled binaries. You will not need it for the warmups, but reading even a little decompiled code opens up the mid-tier malware challenges.

A taste of deobfuscation

Here is the kind of line you will meet in a PowerShell challenge. The -enc flag means the command is Base64, and PowerShell encodes it as UTF-16LE, which is why a plain decode looks odd:

powershell -nop -w hidden -enc VwByAGkAdABlAC0ATwB1AHQAcAB1AHQAIAAnAGYAbABhAGcAewBkADMAYwAwAGQAMwBkAF8AbgAwAHQAXwByADMANABsAH0AJwA=

$ echo 'VwByAGkAdABl...ACcA=' | base64 -d | iconv -f UTF-16LE -t UTF-8
Write-Output 'flag{d3c0d3d_n0t_r34l}'

Skip the iconv step and you get the same text padded with invisible null bytes, which trips up a lot of beginners. In CyberChef, the equivalent recipe is "From Base64" followed by "Decode text" set to UTF-16LE. Real challenges stack several of these layers, but each layer is this simple. The Base64 Detective lab is a gentle way to build the habit of spotting encoded strings in places you would not normally look.

A four-week plan for September

1. Week 1: lab and warmups. Build your VM, take a clean snapshot, and solve a few beginner forensics challenges to get used to file, strings, and CyberChef.
2. Week 2: logs and email. Practice reading web server logs and email headers until you can tell a normal request from an attack at a glance. Our Log Hunter lab asks you to find the single request where an attacker got a file out.
3. Week 3: scripts. Take a few obfuscated PowerShell, JavaScript, or VBA samples from past write-ups and decode them by hand. The goal is to recognize patterns like Base64, string reversal, and character code arrays.
4. Week 4: past editions. Read the 2024 and 2025 retros, then two or three public write-ups for challenges in your chosen category. Join the Discord and register as soon as registration opens.

How to Play Your First Huntress CTF Month

Thirty-one days is long. The players who finish strong treat it as a routine, not a sprint.

• ⏰Check in every day. New challenges appear each morning (9 AM Eastern in 2026). Read them all, even ones outside your category, and pick one to attempt.
• 📝Keep a notes file per challenge. Write down every command and dead end. It saves time when a similar challenge shows up two weeks later, and it becomes your write-up in November.
• ⏳Timebox the hard ones. Give a challenge one evening. If you are still stuck, park it and come back after a later challenge teaches you something new.
• 💬Use Discord for hints, not answers. The community is helpful, but asking for a flag teaches you nothing.

When it is over, practice does not have to stop. Just Hacking Training, the training company John Hammond co-founded, sells a playable archive of the 2023 edition for $20, with no time limits and no scoreboard. Its page lists 43 challenges (fewer than the 58 counted during the live event), focused on forensics and malware.

Huntress CTF vs Other Beginner Competitions

The Huntress CTF is not the only free event that suits newcomers. If October is too far away, or you want a different flavor, here is how it compares with other yearly favorites. Our guide to entering your first CTF competition covers the wider calendar.

Our take: if you liked the Huntress CTF, December's Advent of Cyber is the natural next step. It keeps the one-challenge-a-day rhythm but holds your hand more, which makes it a good way to fill the gaps October exposed.

Legal and Ethical Considerations

• Treat samples as live malware. Keep them in an isolated VM, do not upload them to work machines, and delete them when you are done.
• Do not publish solutions during the event. Organizers have asked players to wait until after the CTF closes (in 2023, at least 24 hours after the end) before posting write-ups. Write now, publish in November.
• Stay inside the scope. Only the challenge targets are fair game. Attacking the platform itself, other players, or Huntress's real infrastructure is off limits.

Frequently Asked Questions