mirror of
https://github.com/mukul975/Anthropic-Cybersecurity-Skills.git
synced 2026-07-20 14:30:59 +03:00
Mapped every skill to NIST CSF 2.0 subcategory IDs (GV/ID/PR/DE/RS/RC functions) based on subdomain and content analysis. Restores 11 skills corrupted during prior rebase, re-enriching with ATLAS, D3FEND, NIST AI RMF, and CSF 2.0 fields. All 754 skills now carry structured mappings for all 5 security frameworks: - MITRE ATT&CK (in tags) - MITRE ATLAS v5.5 (atlas_techniques) - MITRE D3FEND v1.3 (d3fend_techniques) - NIST AI RMF 1.0 (nist_ai_rmf) - NIST CSF 2.0 (nist_csf)
354 lines
12 KiB
Markdown
354 lines
12 KiB
Markdown
---
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name: analyzing-outlook-pst-for-email-forensics
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description: Analyze Microsoft Outlook PST and OST files for email forensic evidence including message content, headers, attachments,
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deleted items, and metadata using libpff, pst-utils, and forensic email analysis tools for legal investigations and incident
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response.
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domain: cybersecurity
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subdomain: digital-forensics
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tags:
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- email-forensics
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- pst
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- ost
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- outlook
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- mapi
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- email-headers
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- attachments
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- deleted-emails
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- libpff
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- eml-extraction
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version: '1.0'
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author: mahipal
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license: Apache-2.0
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nist_ai_rmf:
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- MANAGE-2.4
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- MANAGE-3.1
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- MEASURE-3.1
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nist_csf:
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- RS.AN-01
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- RS.AN-03
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- DE.AE-02
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- RS.MA-01
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---
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# Analyzing Outlook PST for Email Forensics
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## Overview
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Microsoft Outlook PST (Personal Storage Table) and OST (Offline Storage Table) files are critical evidence sources in digital forensics investigations. PST files store email messages, calendar events, contacts, tasks, and notes in a proprietary binary format based on the MAPI (Messaging Application Programming Interface) property system. Forensic analysis of these files enables recovery of deleted emails (from the Recoverable Items folder), extraction of email headers for tracing message routes, analysis of attachments for malware or exfiltrated data, and reconstruction of communication patterns. Modern PST files use Unicode format with 4KB pages and can grow up to 50GB, while legacy ANSI format is limited to 2GB.
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## When to Use
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- When investigating security incidents that require analyzing outlook pst for email forensics
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- When building detection rules or threat hunting queries for this domain
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- When SOC analysts need structured procedures for this analysis type
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- When validating security monitoring coverage for related attack techniques
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## Prerequisites
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- libpff/pffexport (open-source PST parser)
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- Python 3.8+ with pypff or libratom libraries
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- MailXaminer, Forensic Email Collector, or SysTools PST Forensics (commercial)
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- Microsoft Outlook (optional, for native PST access)
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- Sufficient disk space for extracted content
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## PST File Locations
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| Source | Path |
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|--------|------|
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| Outlook 2016+ Default | %USERPROFILE%\Documents\Outlook Files\*.pst |
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| Outlook Legacy | %LOCALAPPDATA%\Microsoft\Outlook\*.pst |
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| OST Cache | %LOCALAPPDATA%\Microsoft\Outlook\*.ost |
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| Archive | %USERPROFILE%\Documents\Outlook Files\archive.pst |
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## Analysis with Open-Source Tools
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### libpff / pffexport
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```bash
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# Export all items from PST file
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pffexport -m all evidence.pst -t exported_pst
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# Export only email messages
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pffexport -m items evidence.pst -t exported_emails
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# Export recovered/deleted items
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pffexport -m recovered evidence.pst -t recovered_items
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# Get PST file information
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pffinfo evidence.pst
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```
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### Python PST Analysis
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```python
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import pypff
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import os
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import json
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import hashlib
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import email
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import sys
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from datetime import datetime
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from collections import defaultdict
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class PSTForensicAnalyzer:
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"""Forensic analysis of Outlook PST/OST files."""
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def __init__(self, pst_path: str, output_dir: str):
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self.pst_path = pst_path
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self.output_dir = output_dir
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os.makedirs(output_dir, exist_ok=True)
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self.pst = pypff.file()
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self.pst.open(pst_path)
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self.messages = []
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self.attachments = []
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self.stats = defaultdict(int)
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def process_folder(self, folder, folder_path: str = ""):
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"""Recursively process PST folders and extract messages."""
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folder_name = folder.name or "Root"
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current_path = f"{folder_path}/{folder_name}" if folder_path else folder_name
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for i in range(folder.number_of_sub_messages):
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try:
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message = folder.get_sub_message(i)
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msg_data = self.extract_message(message, current_path)
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if msg_data:
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self.messages.append(msg_data)
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self.stats["total_messages"] += 1
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except Exception as e:
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self.stats["parse_errors"] += 1
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for i in range(folder.number_of_sub_folders):
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try:
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subfolder = folder.get_sub_folder(i)
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self.process_folder(subfolder, current_path)
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except Exception:
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continue
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def extract_message(self, message, folder_path: str) -> dict:
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"""Extract forensic metadata from a single email message."""
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msg_data = {
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"folder": folder_path,
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"subject": message.subject or "",
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"sender": message.sender_name or "",
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"sender_email": "",
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"creation_time": str(message.creation_time) if message.creation_time else None,
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"delivery_time": str(message.delivery_time) if message.delivery_time else None,
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"modification_time": str(message.modification_time) if message.modification_time else None,
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"has_attachments": message.number_of_attachments > 0,
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"attachment_count": message.number_of_attachments,
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"body_size": len(message.plain_text_body or b""),
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"html_size": len(message.html_body or b""),
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}
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# Extract transport headers for routing analysis
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headers = message.transport_headers
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if headers:
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msg_data["headers_present"] = True
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msg_data["headers_size"] = len(headers)
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# Parse key headers
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parsed = email.message_from_string(headers)
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msg_data["from_header"] = parsed.get("From", "")
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msg_data["to_header"] = parsed.get("To", "")
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msg_data["date_header"] = parsed.get("Date", "")
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msg_data["message_id"] = parsed.get("Message-ID", "")
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msg_data["x_originating_ip"] = parsed.get("X-Originating-IP", "")
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msg_data["received_headers"] = parsed.get_all("Received", [])
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# Process attachments
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for j in range(message.number_of_attachments):
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try:
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attachment = message.get_attachment(j)
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att_data = {
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"message_subject": msg_data["subject"],
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"name": attachment.name or f"attachment_{j}",
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"size": attachment.size,
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"content_type": "",
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}
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self.attachments.append(att_data)
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self.stats["total_attachments"] += 1
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except Exception:
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continue
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return msg_data
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def save_attachments(self, max_size_mb: int = 100):
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"""Export attachments to disk for analysis."""
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att_dir = os.path.join(self.output_dir, "attachments")
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os.makedirs(att_dir, exist_ok=True)
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root = self.pst.get_root_folder()
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self._save_attachments_recursive(root, att_dir, max_size_mb)
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def _save_attachments_recursive(self, folder, att_dir, max_size_mb):
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for i in range(folder.number_of_sub_messages):
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try:
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message = folder.get_sub_message(i)
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for j in range(message.number_of_attachments):
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att = message.get_attachment(j)
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if att.size and att.size < max_size_mb * 1024 * 1024:
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name = att.name or f"unknown_{i}_{j}"
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safe_name = "".join(c if c.isalnum() or c in ".-_" else "_" for c in name)
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path = os.path.join(att_dir, safe_name)
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try:
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data = att.read_buffer(att.size)
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with open(path, "wb") as f:
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f.write(data)
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except Exception:
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continue
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except Exception:
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continue
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for i in range(folder.number_of_sub_folders):
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try:
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self._save_attachments_recursive(folder.get_sub_folder(i), att_dir, max_size_mb)
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except Exception:
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continue
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def generate_report(self) -> str:
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"""Generate comprehensive PST forensic analysis report."""
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root = self.pst.get_root_folder()
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self.process_folder(root)
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report = {
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"analysis_timestamp": datetime.now().isoformat(),
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"pst_file": self.pst_path,
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"pst_size_bytes": os.path.getsize(self.pst_path),
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"statistics": dict(self.stats),
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"messages": self.messages[:500],
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"attachments": self.attachments[:200],
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}
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report_path = os.path.join(self.output_dir, "pst_forensic_report.json")
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with open(report_path, "w") as f:
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json.dump(report, f, indent=2, default=str)
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print(f"[*] Total messages: {self.stats['total_messages']}")
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print(f"[*] Total attachments: {self.stats['total_attachments']}")
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print(f"[*] Parse errors: {self.stats['parse_errors']}")
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return report_path
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def close(self):
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self.pst.close()
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def main():
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if len(sys.argv) < 3:
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print("Usage: python process.py <pst_file> <output_dir>")
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sys.exit(1)
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analyzer = PSTForensicAnalyzer(sys.argv[1], sys.argv[2])
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analyzer.generate_report()
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analyzer.close()
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if __name__ == "__main__":
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main()
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```
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## Email Header Analysis
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Key headers for forensic investigation:
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| Header | Forensic Value |
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|--------|---------------|
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| Received | Message routing chain (read bottom to top) |
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| X-Originating-IP | Sender's actual IP address |
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| Message-ID | Unique identifier for correlation |
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| Date | Send timestamp |
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| Return-Path | Bounce address (may differ from From) |
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| DKIM-Signature | Domain authentication signature |
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| Authentication-Results | SPF, DKIM, DMARC verification results |
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| X-Mailer | Email client used |
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## References
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- MailXaminer PST Forensics: https://www.mailxaminer.com/blog/outlook-pst-file-forensics/
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- libpff Documentation: https://github.com/libyal/libpff
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- PST File Format Specification: https://docs.microsoft.com/en-us/openspecs/office_file_formats/ms-pst/
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- SANS Email Forensics: https://www.sans.org/blog/email-forensics/
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## Example Output
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```text
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$ pffexport /evidence/jsmith_archive.pst -t /analysis/pst_output
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pffexport 20231205 - libpff PST/OST Export Tool
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=================================================
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Input: /evidence/jsmith_archive.pst (2.3 GB)
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Exporting PST contents...
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Folders: 45
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Messages: 12,456
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Attachments: 3,234
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Contacts: 567
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Calendar: 234
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Tasks: 89
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Export completed in 3m 42s.
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$ python3 pst_analyzer.py /analysis/pst_output /analysis/email_report
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PST Forensic Analysis Report
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==============================
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Source: jsmith_archive.pst (john.smith@corporate.com)
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Date Range: 2023-06-01 to 2024-01-18
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--- Mailbox Statistics ---
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Total Emails: 12,456
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Sent: 4,567
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Received: 7,889
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With Attachments: 3,234
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Deleted (recovered): 234
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--- Phishing / Suspicious Emails ---
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Email #8923
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Date: 2024-01-15 14:30:22 UTC
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From: "IT Support" <it-support@c0rporate-help.com>
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To: john.smith@corporate.com
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Subject: Urgent: Password Reset Required
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Headers:
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Return-Path: bounce@mail-relay.c0rporate-help.com
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X-Originating-IP: 203.0.113.55
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Received: from mail-relay.c0rporate-help.com (203.0.113.55)
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SPF: FAIL (domain c0rporate-help.com)
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DKIM: NONE
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DMARC: FAIL
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Attachments:
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- Password_Reset_Form.xlsm (245 KB) SHA-256: 7a3b8c9d...e1f2a3b4
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Body Preview: "Dear Employee, Your password will expire in 24 hours.
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Please open the attached form to reset your credentials..."
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--- Data Exfiltration Indicators ---
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Email #9102
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Date: 2024-01-16 03:15:45 UTC
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From: john.smith@corporate.com
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To: j.smith.personal8842@protonmail.com
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Subject: (no subject)
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Attachments:
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- archive_part1.7z (24.5 MB) - encrypted
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- archive_part2.7z (24.5 MB) - encrypted
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Email #9103
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Date: 2024-01-16 03:18:22 UTC
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From: john.smith@corporate.com
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To: j.smith.personal8842@protonmail.com
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Subject: Re:
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Attachments:
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- archive_part3.7z (18.2 MB) - encrypted
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--- Keyword Hits ---
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"confidential": 45 emails
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"password": 23 emails
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"transfer": 12 emails
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"resign": 3 emails
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"delete evidence": 1 email (Email #9200, 2024-01-17 22:30:00 UTC)
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Summary:
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Phishing emails detected: 1 (initial compromise vector)
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Suspicious sent emails: 5 (to personal accounts with attachments)
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Encrypted attachments: 3 (67.2 MB total - possible exfiltration)
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Report: /analysis/email_report/pst_forensic_report.json
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```
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