We’re introducing new AI-powered capabilities designed to help admins create more tailored learning experiences for their teams.
With these updates, admins can now define team upskilling preferences more easily and generate custom learning paths with AI support.
- Upskilling Preferences AI
- Create Learning Path with AI
- How these features work together
- Security and Data Privacy
- Additional Information
Upskilling Preferences AI
Overview
Upskilling Preferences AI helps enterprise administrators define team learning priorities through AI-guided recommendations. Instead of browsing categories manually, admins can describe team goals and receive relevant preference suggestions.
Availability
Available to enterprise account administrators (Both full and sub-admins).
Preference Categories
Upskilling Preferences are grouped into five categories:
| Category | Description | Examples |
| Job Roles | Roles your team fills or is preparing for | SOC Analyst, Penetration Tester |
| Skills | Technical skills to develop | Network Enumeration, Malware Analysis |
| Attack Areas | Broad security focus areas | Active Directory, Cloud Security |
| Attack Vectors | Specific techniques or methods | Phishing, Credential Stuffing |
| Certifications | Certifications your team is pursuing | OSCP, OSEP, OSED |
To access Upskilling preferences AI
- Log in to the OffSec Platform as an enterprise admin
- Go to the Admin Console
- Open Team Management
- Click the "Upskill Preferences" tab
Chat with AI will look like this if there is no selected preferences yet.
Chat with AI will look like this if there is preferences selected already.
Using the AI Chat
Step 1: Start a conversation
Open Chat with AI or select a suggested prompt.
Step 2: Describe your team
Share your team’s focus, roles, or learning goals.
Step 3: Review suggestions
The AI recommends relevant preferences by category.
Step 4: Add preferences
Use Add to save the preferences you want.
Step 5: Refine as needed
Continue the conversation to adjust, expand, or narrow your selections. Sessions can be resumed across visits.
Example Prompts
Examples include:
- “Suggest preferences for a team of penetration testers”
- “Show me skills related to cloud security”
- “Add more skills related to Active Directory”
- “Remove the phishing attack vector”
- “What are my current preferences?”
Create Learning Path with AI
Overview
Create Learning Path with AI helps enterprise administrators build custom learning paths through a conversational AI interface. Admins describe their team's training goals in natural language, and the AI searches the OffSec content catalog in real time to curate a structured learning path. The AI asks clarifying questions about proficiency level and training commitment, presents a proposed path for review, and supports optional team assignment — all within the same conversation.
Availability
Available to enterprise account administrators (Both full and sub-admins).
Supported Content Types
The AI can recommend content from the OffSec catalog, including:
| Content Type | Description |
| Modules | Theory-based learning material |
| Labs | Hands-on practice environments |
| Assessments | Skill validation through challenges or exams |
| Courses | Structured training programs |
| Learning Paths | Existing curated content sequences |
AI-generated paths typically combine these content types for a balanced learning experience.
To access Create Learning Path AI
- Log in to the OffSec Platform as an enterprise admin
- Go to the Admin Console
- Open the Paths page
- Click "Create with AI"
How Path Creation Works
Step 1: Describe your goal
Tell the AI what your team should learn, including topics, skill level, or time constraints.
Step 2: Review the AI’s suggestions
The AI reviews relevant OffSec content and recommends learning path items based on your selected preferences, goals, and team context.
Step 3: Review the proposed path
The AI presents a suggested path with a summary, content list, and estimated duration.
Step 4: Approve or refine
You can accept the path, request changes, or start over.
Step 5: Assign to your team (optional)
After creation, you can assign the path to learners, groups, or individuals, or do this later from the Paths page.
Example Prompts
Examples include:
- “Create a security fundamentals path for new team members”
- “Build a path focused on Active Directory attack and defense”
- “Create a quick 10-hour path on OWASP Top 10 vulnerabilities”
- “Build a path for our SOC analysts focused on threat detection and response”
How These Features Work Together
Upskilling Preferences AI and Create Learning Path with AI are designed to work together.
Set Preferences First
Define your team’s focus areas, roles, and goals using Upskilling Preferences AI.
Create More Targeted Learning Paths
The AI uses that context to suggest more relevant learning paths.
Refine Over Time
As your team’s needs change, you can update preferences and create new paths.
Example Workflow
- Set preferences: “We’re a red team focused on Active Directory and web application testing, preparing for OSCP.”
- Create a path: “Build a learning path for our team’s OSCP preparation.”
The AI uses that context to generate more relevant recommendations.
Security and Data Privacy
Secure Interactions
Communication between your browser and the OffSec Platform is encrypted, and AI processing uses secure API connections.
As a best practice, avoid sharing unnecessary personally identifiable information (PII) in AI chats.
Sensitive Information
These features are limited to account-level administration. The AI can access the account data needed to support path creation and recommendations, but not sensitive information such as passwords or payment details.
Privacy
OffSec’s privacy policy governs how personally identifiable information is handled, including any information that may be submitted through these AI features.
Conversation Data
Conversations are processed through Anthropic’s API to generate responses and recommendations. OffSec does not share your account data, team information, or conversation history with other third parties, and this data is not used to train AI models.
Additional Information
Access to Team Data
The AI can use existing learning paths, team structure and groups, and content catalog data to recommend relevant training and help avoid duplicate suggestions.
Saved Conversations
Conversations are saved so you can resume them later.
For Create Learning Path with AI, history remains available until you complete a path or start a new one.
For Upskilling Preferences AI, chat history is saved per account and can be resumed across sessions.
Refining Suggestions
Suggestions can be refined within the same conversation. You can ask the AI to adjust learning path content or request different preference recommendations. No changes are made without your action.
Usage
Usage limits are not currently enforced for enterprise administrators; however, feature availability and access policies may change over time.
Availability
These features are being rolled out gradually. If they are not visible in your account, contact your OffSec account representative or OffSec Support.