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Security35k · #5938

implementing-privileged-session-monitoring

Helps your agent monitor and record administrator sessions to ensure actions are secure and auditable.

What it does

This tool helps set up a system to record and monitor sessions of users with special access (administrators, etc.). It ensures everything done during these sessions is logged for security and auditing purposes.

When to use it

  • ✓When configuring administrator access to important systems.
  • ✓When needing to prove that security rules were followed.
  • ✓To investigate suspicious activities after a security incident.

Example of what to ask your AI

“Set up monitoring to record all administrator sessions on production servers.”

Want more? Open the sections below.

How to use

The easiest way: copy the message below and paste it into Claude, ChatGPT, Cursor or any AI. It reads the skill and follows the instructions.

Skill link

https://github.com/mukul975/Anthropic-Cybersecurity-Skills/blob/main/skills/implementing-privileged-session-monitoring/SKILL.md

Ready-to-paste message

Use this skill to help me: https://github.com/mukul975/Anthropic-Cybersecurity-Skills/blob/main/skills/implementing-privileged-session-monitoring/SKILL.md Read the SKILL.md file at that link and follow its instructions for my task.
How it works

The system redirects special access to an intermediate server that records the screen and commands. These recordings are stored securely for later review.

Installation

Easiest way: copy the skill link and paste it into Claude, ChatGPT or Cursor asking it to follow the instructions.

In the terminal (Claude Code, Codex, Cursor), in your project folder:

npx skills add mukul975/Anthropic-Cybersecurity-Skills --skill implementing-privileged-session-monitoring

Or download just the file:

curl -L https://raw.githubusercontent.com/mukul975/Anthropic-Cybersecurity-Skills/main/skills/implementing-privileged-session-monitoring/SKILL.md -o SKILL.md
Technical content (original SKILL.md)

Original text by the author, straight from GitHub.

Implementing Privileged Session Monitoring

When to Use

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

Do not use for monitoring standard user sessions or endpoint activity; use EDR/UBA solutions for general user behavior monitoring. Privileged session monitoring focuses specifically on elevated-access sessions.

Prerequisites

  • CyberArk PAM Self-Hosted or Privilege Cloud deployment with Digital Vault configured
  • CyberArk Privileged Session Manager (PSM) or PSM for SSH (PSMP) installed on a hardened Windows/Linux jump server
  • Network architecture where all privileged access is routed through the PSM proxy (no direct RDP/SSH to targets)
  • PVWA (Password Vault Web Access) deployed and accessible for session review
  • Active Directory integration for authenticating PAM users
  • Sufficient storage for session recordings (estimate: 50-250 KB per minute for RDP, 5-20 KB per minute for SSH)
  • Alternatively for open-source: Teleport, Apache Guacamole with session recording, or script/ttyrec for Linux

Workflow

Step 1: Architecture — Route All Privileged Access Through PSM

Ensure no direct privileged access bypasses the recording proxy:

Architecture Overview:

  Admin User ──> PVWA (Web Portal) ──> PSM (Jump Server) ──> Target Server
       │                                     │                     │
       │         Credentials never           │   Session is        │
       │         exposed to admin            │   recorded and      │
       │                                     │   stored in Vault   │
       └── MFA + AD Auth ──────────────────> │                     │
                                              └── RDP/SSH proxy ──>│

Network Controls:
- Firewall: DENY direct RDP (3389) and SSH (22) to target servers from user networks
- Firewall: ALLOW RDP/SSH to target servers ONLY from PSM server IPs
- Firewall: ALLOW PVWA access (443) from admin user networks
- PSM server: Hardened, no internet access, local admin access restricted

Step 2: Configure PSM Connection Components

Define how PSM connects to target systems. In the PVWA administration console:

PVWA > Administration > Configuration > Connection Components

For Windows RDP targets:
  Connection Component: PSM-RDP
  Protocol: RDP
  Client Application: mstsc.exe
  Recording Settings:
    Record Sessions: Yes
    Recording Format: AVI (video) + Keystrokes (text)
    Record Windows Titles: Yes

For Linux SSH targets:
  Connection Component: PSM-SSH
  Protocol: SSH
  Client Application: PSM-SecureCRT or PSM-Putty
  Recording Settings:
    Record Sessions: Yes
    Recording Format: AVI + Text commands
    Record Unix Commands: Yes

For Database targets (SQL Server Management Studio):
  Connection Component: PSM-SSMS
  Protocol: Custom
  Client Application: SSMS.exe
  Recording Settings:
    Record Sessions: Yes
    Record SQL Queries: Yes (via keystroke logging)

Step 3: Configure Session Recording Policies

Define recording rules based on risk level and compliance requirements:

PVWA > Administration > Platform Management > [Platform] > Session Management

Session Recording Settings:
  Enable Session Recording: Yes
  Recording Type: Record and Save (not just Monitor)

  Keystroke Logging:
    Enable Transcript: Yes
    Enable Window Events: Yes

  Storage:
    Recordings Storage Location: Vault (encrypted, tamper-proof)
    Retention Period: 90 days (adjust per compliance requirement)

    PCI-DSS:  Retain for 1 year, available for 3 months
    SOX:      Retain for 7 years
    HIPAA:    Retain for 6 years

  Compression:
    Enable Recording Compression: Yes
    Compression Level: Medium (balance storage vs. quality)

For granular control, configure per-safe recording policies:

Safe: Production-Servers-Admin
  Record all sessions: Yes

Safe: Development-Servers
  Record all sessions: No (optional for non-production)

Safe: Third-Party-Vendor-Access
  Record all sessions: Yes
  Enable real-time monitoring: Yes

…
FAQ

What are 'privileged sessions'?

These are sessions where a user has elevated permissions, like a system administrator, who can make important changes to computers or networks.

Why record these sessions?

To have a clear record of who did what, when, and on which system, helping to prevent fraud, errors, and to investigate security incidents.

Can I use this to monitor normal users?

No, this tool is specific to users with special access. For regular users, there are other behavior monitoring tools.

Details

Original description by the author

Implements privileged session monitoring and recording using PAM solutions, focusing on CyberArk Privileged Session Manager (PSM) and open-source alternatives, covering session recording configuration, keystroke logging, real-time monitoring, risk-based session analysis, and compliance audit trail generation. Use when configuring CyberArk PSM, recording administrator sessions, or building complian

repo: mukul975/Anthropic-Cybersecurity-Skills

Popularity

GitHub stars
35k
Ranking position
#5938
License
Apache-2.0
Updated
8/31/2026

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