
~/roadmaps/offensive
Red Team Operator
Recon, exploitation, AD attacks, and reporting.
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Red Team Operator Roadmap: step-by-step
21 steps in order. Open any step in the map above to track progress and take notes.
Orientation
1.Start here
Start· Beginner· ~0.5h
Kick off the Red Team Operator path. Review prerequisites, set a weekly study cadence, and follow recommended nodes first.
- Confirm prerequisites
- Bookmark this roadmap
- Plan your first 2 weeks
Core skills
2.Engagement scoping
Concept· Advanced· ~2h
Build competence in Engagement scoping for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Engagement scoping
- Apply Engagement scoping in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
3.OSINT and recon
Concept· Advanced· ~3h
Build competence in OSINT and recon for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind OSINT and recon
- Apply OSINT and recon in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
4.External attack surface
Concept· Advanced· ~4h
Build competence in External attack surface for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind External attack surface
- Apply External attack surface in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
5.Web exploitation core
Tool· Advanced· ~2h
Build competence in Web exploitation core for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Web exploitation core
- Apply Web exploitation core in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
6.Initial access techniques
Lab· Advanced· ~3h
Build competence in Initial access techniques for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Initial access techniques
- Apply Initial access techniques in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
7.Payload delivery OPSEC
Concept· Advanced· ~4h
Build competence in Payload delivery OPSEC for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Payload delivery OPSEC
- Apply Payload delivery OPSEC in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
8.Privilege escalation Linux
Concept· Advanced· ~2h
Build competence in Privilege escalation Linux for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Privilege escalation Linux
- Apply Privilege escalation Linux in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
9.Privilege escalation Windows
Tool· Advanced· ~3h
Build competence in Privilege escalation Windows for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Privilege escalation Windows
- Apply Privilege escalation Windows in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
10.Active Directory attacks
Concept· Advanced· ~4h
Build competence in Active Directory attacks for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Active Directory attacks
- Apply Active Directory attacks in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
Advanced practice
11.Lateral movement
Lab· Advanced· ~2h
Build competence in Lateral movement for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Lateral movement
- Apply Lateral movement in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
12.Credential access
Concept· Advanced· ~3h
Build competence in Credential access for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Credential access
- Apply Credential access in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
13.C2 fundamentals
Tool· Advanced· ~4h
Build competence in C2 fundamentals for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind C2 fundamentals
- Apply C2 fundamentals in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
14.Evasion concepts
Concept· Advanced· ~2h
Build competence in Evasion concepts for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Evasion concepts
- Apply Evasion concepts in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
15.Exfiltration tradecraft
Concept· Advanced· ~3h
Build competence in Exfiltration tradecraft for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Exfiltration tradecraft
- Apply Exfiltration tradecraft in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
16.Reporting that matters
Lab· Advanced· ~4h
Build competence in Reporting that matters for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Reporting that matters
- Apply Reporting that matters in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
17.Purple team debrief
Tool· Advanced· ~2h
Build competence in Purple team debrief for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Purple team debrief
- Apply Purple team debrief in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
18.Ethics and rules of engagement
Concept· Advanced· ~3h
Build competence in Ethics and rules of engagement for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Ethics and rules of engagement
- Apply Ethics and rules of engagement in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
19.Capstone scenario
Concept· Advanced· ~4h
Build competence in Capstone scenario for the Red Team Operator track. Focus on practical application, not trivia.
- Explain core ideas behind Capstone scenario
- Apply Capstone scenario in a lab or exercise
- Document findings in your notes
Tools & tech: Red Team
Assessment
20.Skills checkpoint
Checkpoint· Advanced· ~2h
Validate readiness before finishing Red Team Operator. Revisit weak nodes and close open exercises.
- Self-assess gaps
- Retake weak labs
- Update portfolio notes
Capstone
21.Red Team Operator — ready
Finish· Advanced· ~1h
You completed the Red Team Operator roadmap. Keep practicing, contribute writeups, and start an adjacent track.
- Ship a portfolio artifact
- Choose a next roadmap
Continue learning
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