Anthropic-Cybersecurity-Skills/skills/implementing-privileged-session-monitoring/SKILL.md

name, description, domain, subdomain, tags, version, author, license

name	description	domain	subdomain	tags	version	author	license
implementing-privileged-session-monitoring	Monitor and audit privileged user sessions including SSH, RDP, and database access. Tracks session metadata, records commands, detects anomalous activity, and enforces session policies for PAM compliance.	cybersecurity	identity-access-management	pam session-monitoring privileged-access audit-logging	1.0	mahipal	Apache-2.0

Implementing Privileged Session Monitoring

When to Use

• Deploying session recording for all privileged access to critical servers and databases
• Meeting compliance requirements (PCI-DSS 10.2, SOX, HIPAA, ISO 27001) mandating privileged activity monitoring
• Investigating incidents where an administrator may have performed unauthorized actions
• Implementing real-time alerting for high-risk commands during privileged sessions
• Establishing a forensic audit trail of all administrative actions on production infrastructure

Do not use for monitoring standard user sessions; use EDR/UBA for general user behavior monitoring.

Prerequisites

• CyberArk PAM or Privilege Cloud with Digital Vault, or open-source alternative (Teleport)
• PSM (Privileged Session Manager) or PSMP installed on hardened jump server
• Network architecture routing all privileged access through the PSM proxy
• Sufficient storage for recordings (estimate: 50-250 KB/min for RDP, 5-20 KB/min for SSH)

Workflow

Step 1: Route All Privileged Access Through PSM

Architecture:
  Admin User --> PVWA (Web Portal) --> PSM (Jump Server) --> Target Server

Network Controls:
  - DENY direct RDP (3389) / SSH (22) to targets from user networks
  - ALLOW RDP/SSH to targets ONLY from PSM server IPs
  - ALLOW PVWA access (443) from admin user networks

Step 2: Configure PSM Connection Components

PVWA > Administration > Connection Components

For Windows RDP:
  Connection Component: PSM-RDP
  Record Sessions: Yes
  Recording Format: AVI (video) + Keystrokes (text)
  Record Windows Titles: Yes

For Linux SSH:
  Connection Component: PSM-SSH
  Record Sessions: Yes
  Record Unix Commands: Yes

Step 3: Configure Session Recording Policies

PVWA > Platform Management > Session Management

  Enable Session Recording: Yes
  Keystroke Logging: Enable Transcript + Window Events
  Storage: Vault (encrypted, tamper-proof)

  Retention periods (per compliance):
    PCI-DSS:  1 year available, 3 months accessible
    SOX:      7 years
    HIPAA:    6 years

  Per-Safe policies:
    Production-Servers-Admin: Record all, real-time monitoring
    Third-Party-Vendor-Access: Record all, dual authorization required

Step 4: Enable Real-Time Monitoring and Alerting

Configure CyberArk Privileged Threat Analytics (PTA):

PTA > Configuration > Security Events

Rule: High-Risk Command Detected
  Trigger patterns:
    - rm -rf /
    - chmod 777
    - useradd / passwd root
    - wget http* | sh / curl * | bash
    - nc -e /bin/sh
  Action: Alert SOC + Flag session as high-risk

Rule: Credential Access Attempt
  Trigger:
    - mimikatz.exe
    - procdump.exe targeting lsass
    - ntdsutil.exe
  Action: Terminate session + Alert SOC + Lock account

Rule: Unusual Session Duration
  Trigger: Session > 4 hours
  Action: Alert SOC for review

Step 5: Configure Session Review Workflow

PVWA > Recordings > Search and Review

Review features:
  - Video playback with timeline scrubbing
  - Keystroke transcript alongside video
  - Window title log for application tracking
  - Risk events highlighted on timeline
  - Text search within keystroke transcript
  - Auditor can mark: Reviewed-OK, Suspicious, Requires-Investigation

Step 6: Open-Source Alternative - Teleport

# /etc/teleport.yaml
teleport:
  nodename: teleport-proxy.corp.internal

auth_service:
  enabled: yes
  session_recording: "node-sync"
  audit_sessions_uri: "s3://teleport-session-recordings/sessions?region=us-east-1"
  enhanced_recording:
    enabled: true
    command_events: true
    network_events: true

# List recorded sessions
tsh recordings ls --from=2026-03-15

# Play back a session
tsh play <session-id>

# Export session events for SIEM
tsh recordings export <session-id> --format=json > session_events.json

Step 7: Forward Session Metadata to SIEM

CyberArk PTA > SIEM Integration
  Protocol: TCP + TLS (Syslog CEF)
  Destination: siem.corp.internal:6514

Events forwarded:
  - Session start/stop with user, target, duration
  - High-risk command alerts
  - Session termination events
  - Dual-authorization approvals/denials

Key Concepts

Term	Definition
PSM	Privileged Session Manager - proxy recording all sessions in video and text
PSMP	PSM for SSH Proxy - Linux-based proxy for SSH, SCP, SFTP sessions
PTA	Privileged Threat Analytics - behavioral analytics and risk scoring for sessions
Dual Authorization	Two authorized users must approve before a privileged session is established
Session Isolation	All admin access proxied through PAM; no direct connections to targets
Keystroke Transcript	Searchable text log of all keystrokes during a recorded session

Verification

• All privileged access routes through PSM (direct RDP/SSH blocked by firewall)
• Session recordings stored encrypted with tamper protection
• Keystroke transcripts captured and searchable for SSH and RDP
• PTA rules trigger alerts for high-risk commands (test with benign trigger)
• Real-time monitoring dashboard shows active sessions with correct metadata
• Recordings play back in PVWA HTML5 player with timeline and transcript
• Retention policies match compliance requirements
• Dual authorization enforced for vendor and high-risk access
• Session metadata and alerts forwarding to SIEM