Capture the Flag Hacking Challenge
Operation Hollow Crown
Operation Hollow Crown
Ready to prove your skills in a real-world hacking scenario?
Join Red Sentry & AP2T Lab's virtual Capture the Flag (CTF) competition—a cybersecurity challenge built by ethical hackers, for ethical hackers.
Capture the Flag Hacking Challenge
Operation Hollow Crown
Ready to prove your skills in a real-world hacking scenario?
Join Red Sentry & AP2T Lab's virtual Capture the Flag (CTF) competition—a cybersecurity challenge built by ethical hackers, for ethical hackers.
EVENT OVERVIEW
Pentest CTF
Round 1 of this CTF: Operation Hollow Crown is an invite-only remote CTF from Red Sentry and AP2T Labs designed for MSPs, MSSPs, and IT Service Providers to sharpen their offensive skills!
Teams will begin by investigating simulated dark web data, employee clues, and credential leaks before using AI social engineering to gain access to a cloud-hosted internal environment. Once inside, teams will follow realistic attack paths, identify exposed secrets and misconfigurations, and capture flags hidden in restricted systems. This is an offense-only event, and teams will not attack each other. Round 1 is intentionally scoped as an elementary-to-intermediate challenge focused on learning, collaboration, and realistic breach progression.
Pentest CTF
Round 1 of this CTF: Operation Hollow Crown is an invite-only remote CTF from Red Sentry and AP2T Labs designed for MSPs, MSSPs, and IT Service Providers to sharpen their offensive skills!
Teams will begin by investigating simulated dark web data, employee clues, and credential leaks before using AI social engineering to gain access to a cloud-hosted internal environment. Once inside, teams will follow realistic attack paths, identify exposed secrets and misconfigurations, and capture flags hidden in restricted systems. This is an offense-only event, and teams will not attack each other. Round 1 is intentionally scoped as an elementary-to-intermediate challenge focused on learning, collaboration, and realistic breach progression.
Meet the CTF Makers
Our Capture the Flag challenges aren’t autogenerated—they’re handcrafted by brilliant minds who live and breathe security. From clever puzzles to complex exploits, these challenges are designed to test your skills and stretch your thinking.
Meet a few of the creators who brought this CTF to life:
remonsec
Global CTF Challenge Creator
->
Jesse "Hackah Jak" Tuttle
Former World's Most Wanted Hacker
->
Meet the CTF Makers
Our Capture the Flag challenges aren’t autogenerated—they’re handcrafted by brilliant minds who live and breathe security. From clever puzzles to complex exploits, these challenges are designed to test your skills and stretch your thinking.
Meet a few of the creators who brought this CTF to life:
remonsec
Global CTF Challenge Creator
->
Jesse "Hackah Jak" Tuttle
Former World's Most Wanted Hacker
->
Meet the CTF Makers
Our Capture the Flag challenges aren’t autogenerated—they’re handcrafted by brilliant minds who live and breathe security. From clever puzzles to complex exploits, these challenges are designed to test your skills and stretch your thinking.
Meet a few of the creators who brought this CTF to life:
remonsec
Global CTF Challenge Creator
->
Jesse "Hackah Jak" Tuttle
Former World's Most Wanted Hacker
->
Meet the CTF Makers
Our Capture the Flag challenges aren’t autogenerated—they’re handcrafted by brilliant minds who live and breathe security. From clever puzzles to complex exploits, these challenges are designed to test your skills and stretch your thinking.
Meet a few of the creators who brought this CTF to life:
remonsec
Global CTF Challenge Creator
->
Jesse "Hackah Jak" Tuttle
Former World's Most Wanted Hacker
->
6.26 — 7.5
DATE
->
24h CHALLENGE WINDOW
TIME
->
Virtual
LOCATION
->
Up to 6 people*
TEAMS
->
Difficulty
->
Free
COST
->
*Open to all MSPs and IT Service Teams
Spots are limited, and Red Sentry and AP2T Partners will be prioritized for registration.
6.26 — 7.5
DATE
->
24h CHALLENGE WINDOW
TIME
->
Virtual
LOCATION
->
Up to 6 people*
TEAMS
->
Difficulty
->
Free
COST
->
*Open to all MSPs and IT Service Teams
Spots are limited, and Red Sentry and AP2T Partners will be prioritized for registration.
6.26 — 7.5
DATE
->
24h CHALLENGE WINDOW
TIME
->
Virtual
LOCATION
->
Up to 6 people*
TEAMS
->
Difficulty
->
Free
COST
->
*Open to all MSPs and IT Service Teams
Spots are limited, and Red Sentry and AP2T Partners will be prioritized for registration.
Want to create your own challenge for a future CTF?
Want to create your own challenge for a future CTF?
We’re always looking for passionate contributors. Reach out to our team to learn more about becoming a challenge author.
Rewards & Recognition
Rewards & Recognition
Our CTF is all about sharpening skills, building community, and having a blast. But let’s be honest, bragging rights and sweet prizes make it even better.
We're still finalizing prize packages—stay tuned for more!
TOP PERFORMERS
TOP PERFORMERS
PLACE
TEAM
TEAM
score
1
2097
Travanauts
2
2089
ThreatExploit
3
2017
ISP1337Hackers
4
Swag City
5
Apesec.ch
6
Light Tech
7
TotalEclipseoftheHeart
8
Deez Defenders
9
Red Defenders
Companies Represented in the Competition
Awards per team
1º
1º
Travanauts
Travanauts
2º
2º
ThreatExploit AI
ThreatExploit AI
3º
3º
ISP1337Hackers
ISP1337Hackers
Best BEC Attack
Best BEC Attack
Net-Tech.us
Net-Tech.us
Best Bug Hunters
Best Bug Hunters
Red Defenders
Red Defenders
Best Left of Boom Attack
Best Left of Boom Attack
Swag City
Swag City
Best Persistent Threat
Best Persistent Threat
TotalEclipseoftheHeart
TotalEclipseoftheHeart
Best Phishing Attack
Best Phishing Attack
Light Tech
Light Tech