Anthropic-Cybersecurity-Skills/skills/detecting-ransomware-encryption-behavior/SKILL.md

---
name: detecting-ransomware-encryption-behavior
description: 'Detects ransomware encryption activity in real time using entropy
  analysis, file system I/O monitoring (Sysmon, watchdog, psutil), and behavioral
  scoring to identify mass file modification, abnormal entropy spikes in written
  data, and suspicious process behavior characteristic of encryption routines.
  Use when building real-time ransomware detection, tuning entropy thresholds,
  or investigating suspected active encryption on an endpoint.

  '
domain: cybersecurity
subdomain: ransomware-defense
tags:
- ransomware
- detection
- entropy
- behavioral-analysis
- file-monitoring
- heuristics
version: 1.0.0
author: mahipal
license: Apache-2.0
nist_csf:
- PR.DS-11
- RS.MA-01
- RC.RP-01
- PR.IR-01
mitre_attack:
- T1078
- T1190
- T1059
- T1486
- T1490
mitre_f3:
  version: '1.1'
  tactics:
  - monetization
  - positioning
  - stealth
  techniques:
  - id: F1018
    name: Convert to Cryptocurrency
    tactic: monetization
    source: f3
  - id: F1017.001
    name: 'Conversion to Physical Monetary Instruments: Cash'
    tactic: monetization
    source: f3
  - id: T1219
    name: Remote Access Tools
    tactic: positioning
    source: attack
  - id: T1070
    name: Indicator Removal
    tactic: stealth
    source: attack
---

# Detecting Ransomware Encryption Behavior

## When to Use

- Building or tuning a behavioral detection layer for ransomware that catches unknown/zero-day variants
- Monitoring file servers and endpoints for mass encryption activity that evades signature-based detection
- Implementing entropy-based detection to identify when files are being replaced with encrypted (high-entropy) content
- Analyzing suspicious process behavior patterns: rapid sequential file opens, writes, renames, and deletes
- Validating EDR detection rules against actual ransomware encryption patterns during red team exercises

**Do not use** entropy analysis alone as the only detection signal. Compressed files (ZIP, JPEG, MP4) naturally have high entropy and will cause false positives. Always combine entropy with behavioral signals like I/O rate and file rename patterns.

## Prerequisites

- Python 3.8+ with `watchdog` and `psutil` libraries
- Administrative access for process monitoring and file system event capture
- Understanding of Shannon entropy and its application to file content analysis
- Windows: Sysmon installed for detailed process and file system event logging
- Linux: auditd configured for file access monitoring, or inotify-based watchers
- Baseline entropy values for common file types in the monitored environment

## Workflow

### Step 1: Establish Entropy Baselines

Calculate normal entropy ranges for files in the environment:

```
Entropy Baselines by File Type:
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
File Type       Normal Entropy    Encrypted Entropy
.docx           3.5 - 6.5        7.8 - 8.0
.xlsx           4.0 - 6.8        7.8 - 8.0
.pdf            5.0 - 7.2        7.8 - 8.0
.txt            2.0 - 5.0        7.8 - 8.0
.csv            2.0 - 5.5        7.8 - 8.0
.sql            2.5 - 5.0        7.8 - 8.0
.jpg/.png       7.0 - 7.9        7.9 - 8.0 (hard to distinguish)
.zip/.7z        7.5 - 8.0        7.9 - 8.0 (hard to distinguish)

Key insight: Text-based files show the largest entropy jump when encrypted,
making them the best candidates for entropy-based detection.
```

### Step 2: Implement Real-Time Entropy Monitoring

Monitor file writes and calculate entropy of new content:

```python
import math
from collections import Counter

def shannon_entropy(data):
    """Calculate Shannon entropy of byte data (0.0 to 8.0 scale)."""
    if not data:
        return 0.0
    freq = Counter(data)
    length = len(data)
    return -sum((c / length) * math.log2(c / length) for c in freq.values())

def is_encryption_entropy(data, threshold=7.5):
    """Check if data entropy indicates encryption."""
    entropy = shannon_entropy(data)
    return entropy >= threshold, entropy
```

### Step 3: Monitor File System I/O Patterns

Track process-level file operations for ransomware patterns:

```
Ransomware I/O Behavior Signatures:
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
1. Rapid sequential file modification:
   - >20 files modified per minute by single process
   - Read original → Write encrypted → Rename with new extension
   - Pattern: CreateFile → ReadFile → WriteFile → CloseHandle → MoveFile

2. File extension changes:
   - Original: report.docx → Encrypted: report.docx.locked
   - Many extensions changed within short time window

3. Ransom note creation:
   - Same text file (README.txt, DECRYPT.html) created in multiple directories
   - Created immediately after file encryption in each directory

4. Shadow copy deletion:
   - vssadmin.exe delete shadows /all /quiet
   - wmic.exe shadowcopy delete
   - PowerShell: Get-WmiObject Win32_Shadowcopy | Remove-WmiObject

5. Entropy spike pattern:
   - File read: entropy 3.5 (normal document)
   - File write: entropy 7.9 (encrypted content)
   - Delta > 3.0 is strong ransomware indicator
```

### Step 4: Implement Behavioral Scoring

Combine multiple signals into a composite ransomware score:

```python
def calculate_ransomware_score(process_metrics):
    """Score process behavior for ransomware likelihood (0-100)."""
    score = 0

    # High file modification rate
    files_per_min = process_metrics.get("files_modified_per_minute", 0)
    if files_per_min > 50:
        score += 30
    elif files_per_min > 20:
        score += 15

    # Entropy increase in written files
    avg_entropy_delta = process_metrics.get("avg_entropy_delta", 0)
    if avg_entropy_delta > 3.0:
        score += 30
    elif avg_entropy_delta > 2.0:
        score += 15

    # File extension changes
    extension_changes = process_metrics.get("extension_changes", 0)
    if extension_changes > 10:
        score += 20
    elif extension_changes > 3:
        score += 10

    # Ransom note creation
    if process_metrics.get("ransom_note_created", False):
        score += 20

    return min(score, 100)
```

### Step 5: Configure Automated Response Thresholds

Set detection thresholds and automated containment actions:

```
Detection Thresholds:
━━━━━━━━━━━━━━━━━━━━
Score 0-25:   INFORMATIONAL - Log only, no action
Score 25-50:  LOW - Alert SOC for investigation
Score 50-75:  HIGH - Alert SOC, suspend process, snapshot VM
Score 75-100: CRITICAL - Kill process, isolate endpoint, alert IR team

Automated Response Actions:
  - Suspend/kill the encrypting process
  - Disable network adapter to prevent lateral movement
  - Create volume shadow copy snapshot before further damage
  - Capture process memory dump for forensic analysis
  - Send SIEM alert with process details, affected files, and timeline
```

## Verification

- Test detection against known ransomware samples in an isolated sandbox environment
- Verify that entropy monitoring correctly identifies encrypted vs. compressed files
- Confirm that behavioral scoring produces low false-positive rates on normal workloads
- Validate automated response actions execute within acceptable time (under 5 seconds)
- Test with multiple ransomware families (LockBit, BlackCat, Conti) to verify coverage
- Benchmark monitoring overhead to ensure it does not degrade endpoint performance

## Key Concepts

| Term | Definition |
|------|------------|
| **Shannon Entropy** | Mathematical measure of randomness in data (0-8 for bytes); encrypted data approaches 8.0, while text files are typically 2-5 |
| **Differential Entropy** | The change in entropy between a file's original and modified content; a spike indicates encryption |
| **I/O Rate Anomaly** | Abnormally high rate of file read/write operations by a single process, characteristic of bulk encryption |
| **Behavioral Scoring** | Combining multiple weak signals (entropy, I/O rate, file renames) into a composite confidence score |
| **Entropy Evasion** | Techniques used by advanced ransomware to defeat entropy detection, such as Base64 encoding output or partial encryption |

## Tools & Systems

- **Sysmon**: Windows system monitor providing detailed file system and process events for behavioral analysis
- **watchdog (Python)**: Cross-platform file system monitoring library for real-time file change detection
- **psutil (Python)**: Process and system monitoring library for tracking per-process I/O statistics
- **Elastic Endpoint**: Commercial endpoint protection with built-in ransomware behavioral detection using canary files
- **Wazuh**: Open-source security platform with file integrity monitoring and active response capabilities