AI/LLM Exploitation Challenges
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AI and LLM Security enthusiasts
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Security researchers
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Reverse Engineers and Exploit developers
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Developers and DevOps engineers focusing on AI Security
Explore the Challenges
What’s Inside?
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Challenge: Ultimate AI Essay Grader
Welcome to the Ultimate Essay Grader. This is an intelligent essay grading application powered by AI that provides instant feedback and comprehensive evaluation for student essays. It supports Automated Grading where you get instant AI-powered grades from A-F and numerical scores from 0-100, for multiple essay types.
It supports Argumentative Essays, Narrative Essays, Research Papers, and Literary Analysis, and gives comprehensive feedback including strengths, areas for improvement, and grammar assessment. It allows uploading essays in .docx or .doc format.
Objective
Trick the AI Grading system to always give you a perfect score by exploiting its LLM logic
Challenge: Smart Workspace Assistant
Smart Workspace Assistant is a realistic workspace management tool that uses an LLM which is a OpenAI GPT to help users manage files, collaborate with teams, and organize their workspace. The developers say that this has the best security possible, but that's what everyone says right?
Objective
You are a penetration tester hired to perform a security audit on the system. Find a way to convince the LLM to use admin tools as a regular user `alice` and read the admin file "secret_key.txt" to get the flag. All this without logging in explicitly as "admin".
Challenge: Smart Workspace Assistant
Welcome to the SecureVault! This challenge focuses on Adversarial Machine Learning vulnerabilities in deployed ML systems. This secure vault system uses machine learning for authentication. The system only grants access when it recognizes a specific handwritten digit.
Objective
You are a RedTeam operator hired to perform a security audit on the system. You've discovered a secure vault system that uses an ML model to authenticate users. The model analyzes uploaded images of handwritten digits and only grants access when it predicts the digit as 9. Your goal is to identify the vulnerability, and craft an adversarial example that fools the model to bypass authentication and unlock the vault to retrieve the flag. Share the script and image that works.
The focus is on adversarial ML, and not prompt injection or steganography. You need to upload an image that the model thinks is digit 9. But you input file should not be an actual digit "9" when viewed in an image viewer.
After You Upload Your Solution:
Review
Certification
Recognition
Earn a Free Certification and Showcase Your AI and LLM security Expertise
Outcomes & Takeaways
Practice prompt injection, access control issues, reverse engineering, static and dynamic analysis, and bypassing security controls that apply to real AI applications.
Real-World Scenarios
Work with multiple binaries that have vulnerabilities ranging from prompt injection, model evasion, to Adversarial perturbations issues that simulate the challenges you'd face in real world cases for AI and LLM exploitation.
Tool Proficiency
Get comfortable using tools like MCP inspector, Cursor, Adversarial Robustness Toolbox, and more in practical settings.
Security Mindset
Train yourself to think like an attacker: identify weaknesses, understand threat models, and build intuition around LLM system attack strategies and defense evasion.
Portfolio-Ready Experience
Build a strong foundation that you can showcase, whether you are applying for security roles or contributing to modern Artificial Intelligence and Model development environments.
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Live Trainings list:
Lead Application Penetration Tester*
A Cybersecurity Testing & Consulting Firm
$150,000 - $180,000 a year
Required Qualifications & Skills
- Bachelor’s degree in Computer Science, Software Engineering, or related field, or equivalent job experience
- Thorough security testing of developer workflows and mobile applications (iPhone and Android), including identification of security issues and vulnerabilities
- Proficiency in multiple programming languages and understanding of secure coding practices
- In-depth source code reviews to identify security flaws or weaknesses that could be exploited in software applications
- Detailed assessments and compilation of findings into reports for further review and action
- Experience with tools like Burp Suite Pro, Checkmarx, Corellium, Synopsys, Acunetix, VeraCode, SAST & DAST Tools, Plextrac, Cloud security (AWS / Azure / Oracle), Postman, SmartBear ReadyAPI, SoapUI, and Hashicorp Vault
Key Responsibilities
- Team Leadership: Lead and mentor penetration testers, ensuring high-quality security assessments
- Mobile & DevOps Security: Conduct security testing of mobile apps (iOS/Android) and integrate security into DevOps pipelines
- Code & Penetration Testing: Perform source code reviews and comprehensive web/mobile penetration testing
- Reporting & Collaboration: Document findings in detailed reports and collaborate with development teams for remediation
- Offensive Security: Execute red team exercises and offensive security operations
- Security Strategy: Develop and implement security testing strategies and best practices
- Global Collaboration: Work with global teams to secure applications
- Automation: Automate security testing within CI/CD pipelines
iOS Application Security Engineer*
A Cyber-Risk Consulting Firm
$150,000 - $200,000 a year
Required Qualifications & Skills
- Proficiency in iOS frameworks (UIKit, Core Data) and Android frameworks
- In-depth knowledge of mobile security vulnerabilities (OWASP Mobile Top 10) and remediation techniques
- Familiarity with mobile security testing tools (e.g., MobSF, Drozer, Burp Suite, OWASP ZAP)
- Extensive experience in iOS application development using Swift/Objective-C, ideally also knowledge of Android (Java/Kotlin) security
- Strong understanding of cryptography principles, secure data storage, and key management
- Experience with mobile reverse engineering tools such as Frida
- Knowledge of App Store and Google Play Store compliance requirements
- Familiarity with advanced encryption techniques and secure app distribution
Key Responsibilities
- Security Architecture & Threat Modeling: Design secure architectures, perform threat modeling, and ensure compliance (OWASP, PCI DSS, NIST)
- Code Reviews & Auditing: Conduct code reviews, participate in security audits, and perform SAST/DAST
- Vulnerability Management & Penetration Testing: Manage vulnerabilities, conduct penetration tests, and analyze threats
Specialist, Offensive Android Security*
A Tech Giant Company
$151,200 - $207,500 a year
Required Qualifications & Skills
- Proficiency in tools for kernel debugging, fuzzing, and penetration testing
- Experience with reverse engineering tools (e.g., IDA Pro & Ghidra), debugging tools (e.g., JTAG/SWD)
- 5+ years of experience in system-level penetration testing and vulnerability research
- Strong knowledge of low-level programming languages such as C and Assembly
Key Responsibilities
Kernel Security Researcher*
$143,100 - $264,200 a year
Required Qualifications & Skills
- Background in secure coding and code auditing
- Knowledge of modern anti-exploitation mitigations and their effectiveness
- Programming background in C, C++, and Python
Preferred Qualifications:
- Knowledge of macOS and iOS security architectures
Key Responsibilities
Mobile Reverse Engineer*
$88,200 - $195,200 a year
Required Qualifications & Skills
- 5+ yrs experience in mobile software reverse engineering
- Experience with Windows, Linux, Android, OS X, and iOS operating system & architecture
- Experience in computer or cell phone architecture, system internals, operating systems, and/or boot process software engineering
Experience with static analysis tools such as IDA Pro, Ghidra and Binary Ninja
- Experience with debugging tools such as WinDbg
- Experience with virtualization, sandboxing, and emulation tools like VMware, KVM, QEMU and others
- Working knowledge of programming languages such as C, C++, .NET, Python, Java, etc.
- Experience debugging mobile application memory and performance issues
Preferred:
- Experience requiring a deep knowledge of Android and a strong passion in mobile industry and mobile development
- Experience developing/designing mobile phone platforms highly desired
- Experience in wireless API's (Wi-Fi, Bluetooth) preferred
- Engineer software scripts in C, C++, and Java with emphasis on prototyping and API extraction
Key Responsibilities
- Research new trends, techniques, and packaging of malicious software to stay current and ready to identify and handle zero-day exploits
- Research behavior of binaries and share detailed understanding of how apps behave at memory/register level in support of technical exploitation operations
- Support efforts to design, prototype, document, test, conduct exploitation automation and transition code analysis methods and tools specific to technical exploitation operations
Senior Lead Security Engineer - Mobile*
$147,700 - $190,000 a year
Required Qualifications & Skills
- Strong understanding of mobile application security risks and mitigation strategies for both Android and iOS platforms
- Experience in implementing or managing mobile security operations
- Familiarity with CI/CD pipelines, DevSecOps methodologies, and secure software development practices
- Ability to collaborate with development teams on security functions & resolutions
- Hands-on practical experience delivering enterprise level cybersecurity solutions and controls
- Strong collaboration and communication skills are essential for working effectively with teams on security implementations
- Ability to evaluate current and emerging technologies to select or recommend the best solutions for future state architecture & enterprise integrations
- Proven experience leading projects from scoping to delivery
Key Responsibilities
- Utilize our mobile security vendors and tools to drive proactive security measures, ensuring optimal configuration, monitoring, and maintenance to safeguard our mobile applications.
- Oversee the deployment, integration, and ongoing support of mobile security tools, ensuring they are effectively utilized and updated.
- Provide technical leadership in securing mobile applications and infrastructure, ensuring compliance with industry standards and best practices.
- Manage the lifecycle of mobile security tools, including planning and executing upgrades to maintain optimal performance and security.
- Work closely with cross-functional teams to enhance security awareness, provide training, and ensure adherence to security protocols. Additionally, serve as a key feedback conduit to the mobile binary scanning team, risk management, and source scanning teams, ensuring continuous improvements in security posture and alignment with organizational security strategies.
Reverse Engineer - Android*
$90,000 - $120,000 a year
Required Qualifications & Skills
- 3-5 years of hands-on experience with Android and reverse engineering
- In-depth understanding of Android internals and the ability to read, comprehend, and analyze source code software
- Familiarity with reverse engineering tools such as Jadx, Ghidra, Frida, IDA Pro, and Burp to perform binary and APK analysis
Key Responsibilities
To give you an idea of how this Reverse Engineer Malware Analysis - Android role would look and feel, here are some things you could expect to do:
- Review malicious applications and SDKs by analyzing, unpacking, and reverse engineering software that compromises Android devices
- Review security policy violations, vulnerabilities, or improper coding practices
- Research threats like APT using Open-Source Intelligence (Virus Total, Web, ExploitDB, MITRE, etc.)
Android Mobile Reverse Engineer*
$100,000 - $150,000 a year
Required Qualifications & Skills
- Expertise in reverse engineering tools
- Knowledge of Android internals
- Strong debugging and analysis skills
- Familiarity with encryption and obfuscation techniques
- Ability to work with disassemblers and debuggers
Desired Qualifications:
- Experience with Android emulator tools
- Familiarity with mobile penetration testing
- Experience with static and dynamic analysis tools
- Knowledge of security exploits in mobile apps
- Ability to develop custom reverse engineering scripts
- Strong communication and reporting abilities
Key Responsibilities
- Deconstruct mobile application code
- Identify and mitigate security risks
- Reverse engineer mobile app binaries
- Conduct security audits on Android systems
- Document findings and create reports
Mobile Implant Software Engineer*
$114,000 - $180,000 a year
Required Qualifications & Skills
- Demonstrated ability to perform advanced research and development on embedded systems, Linux, and iOS platforms
- Strong understanding of network protocols and experience in implementing support for TCP, UDP, and TLS
- Experience in designing, developing, and integrating modular cyber capabilities
- Proficiency in using and integrating CI/CD tools and practices
- Excellent problem-solving skills and the ability to design novel solutions to complex security challenges
- Strong leadership skills with the ability to guide and mentor development teams
- Programming Languages: C, C++, Python, Java, x86 Assembly, MIPS Assembly, Microblaze Assembly, ARM Assembly, ARM64 Assembly, VHDL, Verilog, XML, JSON, HTML
- Tools and Technologies: LLDB/LLVM, IDA Pro, Immunity Debugger, Immunity Canvas, Eclipse, Git, Subversion, Embedded Systems, FPGAs, Docker, Intel Performance Primitives (IPP), High Performance Computing (HPC), REDHAWK, OmniORB CORBA, Software Defined Radios (SDR), Signal Processing, MySQL, PostgreSQL, JDBC, Django, ActiveMQ, Jpype, Pyxb, STOMP
Key Responsibilities
- Design and implement innovative solutions to address operational security challenges
- Architect and develop flexible, modular cyber capabilities in C, C++, and Python
- Triage and analyze public software vulnerabilities (CVEs) for security concerns
- Provide technical support and custom solutions to high-priority customer needs
- Design and develop new client/server data distribution tools
- Implement support for multiple network protocols, including TCP, UDP, and TLS
- Create custom build systems and ensure portability using Docker
- Integrate new projects with CI/CD services to streamline development processes
- Generate and maintain unit tests to enhance the reliability of client/server applications
- Guide the development team in adhering to industry software engineering standards and best practices
iOS Vulnerability Engineer (Software)*
$120,000 - $170,000 a year
Required Qualifications & Skills
- Proficiency in reverse engineering tools
- Expertise in static and dynamic code analysis
- Familiarity with secure coding practices
- Proficiency in iOS development tools (e.g., Xcode)
- Ability to exploit and remediate vulnerabilities
Desired skills:
- Knowledge of ARM assembly
- Experience with fuzz testing methodologies
- Familiarity with jailbreak development
- Understanding of malware analysis techniques
- Expertise in cryptographic protocols
- Proficiency in scripting for automation (e.g., Python)
Key Responsibilities
- Develop mitigation strategies for discovered issues
- Conduct security assessments of iOS applications
- Perform reverse engineering of iOS binaries
- Collaborate with development teams to improve software security
- Document findings and recommend improvements
Android Security Engineer*
An IT Consulting and Services Firm
$115,000 - $165,000 a year
Required Qualifications & Skills
- Static Analysis - decompilation, dissasembly, code auditing
- Dynamic Analysis - debugging monitoring, fuzzing
- Sample Tools - IDA Pro, Ghidra, Radare2, Jadx, Fernflower, Smali, Baksmalu, ADB, JDWP, Android studio, bluestack, Frida, Wireshark, Cyberchef. HTTP interception, Yara, Snort
- Programming (Java/Kotlin, Scripting, Javascript, Encode/Decode, encryption and decryption)
- Android fundamentals (permissions, Manifest, Entry points, Broadcast receivers, exported activities, services, subclasses, Dalvik/ART Virtual machine)
Key Responsibilities
- Conducting static and dynamic analysis
- Providing assessment and evidence to support findings
- Assessing detection and analysis gaps as well as scalable enforcement through detection rules
Information Security Engineer (Android)*
A Large Online Media Provider
$197,000 - $291,000 a year
Required Qualifications & Skills
- 8 years of experience with security assessments or security design reviews or threat modeling
- 8 years of coding experience in one or more general purpose languages
Preferred qualifications:
- Knowledge in programming languages, compilers, static and dynamic analysis techniques
- Experience in Mobile App Development and Android Apps
- Experience implementing sand-boxing infrastructure or low-level systems features and building static analysis tools, linters or compilers
- Experience with open source
Key Responsibilities
- Review and develop secure operational practices, and provide security guidance for engineers and support staff
- Review designs and look for vulnerabilities, both with one-time reviews and longer term engagements
- Look for vulnerabilities with techniques including reverse engineering, fuzzing, and static analysis
- Respond to vulnerabilities with repos, mitigations, and hardening. Surface vulnerability patterns and design them out.
Sr. Android Penetration Tester*
Required Qualifications & Skills
- Strong understanding of malware, phishing attacks, attack vectors, and security best practices
- Knowledge of penetration testing tools, threat modeling, and security frameworks
- Ability to conduct security research, CVE analysis, and adversary simulation
- Strong communication skills to work cross-functionally with engineering and security teams
- Experience working in corporate environments with internal penetration testing teams (preferred over agency-based consulting experience)
- Bachelor’s degree in either Cybersecurity, Computer Science, Information Security, or related field
Preferred Qualifications:
- Certifications in offensive security
- Published CVEs, blog posts, or walkthroughs on security research
- Malware development and reverse engineering experience
- Experience working in top security consulting firms or in-house red teams at major tech companies
- Hands-on experience with firmware penetration testing and IoT security.
Key Responsibilities
- Plan, scope and conduct vulnerability assessment/ Penetration test on internal / external facing public assets such as Web application, Android platform, Android Apps, Backend APIs, and Cloud services
- Research & and conduct adversary simulation for known security threats and identify novel attack vectors to test a system’s relative security readiness
- Conduct Threat modelling, Threat Intelligence and scoping with stakeholders
- Assist in creating and maintaining internal penetration testing and practice within QA team, managing vulnerabilities and tracking until closure
- Build Test harness & required Automation suites and validate attack vectors in Threat Lab
- Co-ordinate with program management, security architects at Internal & offshore sites
- Stays up to date on current tools, technologies, and vulnerabilities to incorporate into testing practices
- Research and developing exploits for zero-day vulnerabilities
- Conduct penetration test on IOT and Firmware Devices
iOS Application Security Engineer*
$125,000 - $175,000 a year
Required Qualifications & Skills
- Bachelor’s degree in Computer Science, Information Security, or a related field, or 5+ years in mobile application development
- Extensive experience in iOS application development using Swift/Objective-C
- In-depth knowledge of mobile security vulnerabilities (OWASP Mobile Top 10) and remediation techniques
- Proficiency in iOS frameworks (UIKit, Core Data) and Android frameworks
- Familiarity with mobile security testing tools (e.g., MobSF, Drozer, Burp Suite, OWASP ZAP)
- Strong understanding of cryptography principles, secure data storage, and key management
Preferred Qualifications:
- Relevant security certifications
- Experience with mobile reverse engineering tools such as Frida
- Knowledge of App Store and Google Play Store compliance requirements
- Familiarity with advanced encryption techniques and secure app distribution
Key Responsibilities
iOS Engineer - Product Security*
$143,100 - $264,200 a year
Required Qualifications & Skills
- 2+ years of iOS app development experience in Swift and/or Objective-C
- Experience and/or strong interest in security/secure programming, digital signatures and PKI
- User interface programming experience with SwiftUI and/or UIKit
- Understanding of computer science fundamentals
- Able to thrive in a reciprocal environment and clearly communicate across teams
Preferred Qualifications:
- Self-motivated, critical, and detail oriented
- Strong debugging and analytical skills
- Familiar with the ISO 18013-5 standard is a plus
- Experience developing software with any of the following frameworks is a plus: ID Verifier API , Verify with Wallet API
- BS or MS in Computer Science, related technical field or equivalent experience
AI Security Engineer*
Required Qualifications
- 2+ years of programming experience in languages like Python, Ruby, Go, Swift, Java, .NET, C++, or another object-oriented language
Key Responsibilities
- Deliver AI security training sessions and provide guidance to internal development teams
- Offer architectural and design recommendations with an AI security focus
- Shape processes, priorities, and decision-making within your team and with partners to drive stronger security outcomes
Offensive AI Security Tester*
Required Qualifications
- Solid understanding of ML/GenAI concepts (LLMs, embeddings, diffusion models) and adversarial ML techniques (such as model extraction, data poisoning, and prompt manipulation)
- Background in cybersecurity red teaming or penetration testing, with strong skills in Python and scripting for automation and test framework development
- Knowledge of AI security standards and frameworks, including NIST AI RMF, MITRE ATLAS, or OWASP LLM Top 10
- Experience with AI/MLOps tools and enterprise integrations (Azure AI, AWS SageMaker, OpenAI API, Hugging Face, LangChain, or similar platforms)
Nice-to-Haves:
- Experience integrating AI with SIEM/SOAR platforms and threat intelligence monitoring
- Background in creating reusable adversarial testing assets, scripts, and automated workflows
Adversarial Prompt Expert*
Required Qualifications & Skills
- Creativity and persistence, with the ability to explore edge cases and iterate through multiple variations
- Strong documentation skills to record tests, track outcomes, and communicate findings clearly
- Solid ethical judgment, with an understanding of boundaries and responsible handling of sensitive material