Investigating Phishing Email Incident

When to Use

Use this skill when:

• A user reports a suspicious email via the phishing report button or helpdesk ticket
• Email security gateway flags a message that bypassed initial filters
• Automated detection identifies credential harvesting URLs or malicious attachments
• A phishing campaign targeting the organization requires scope assessment

Do not use for spam or marketing emails without malicious intent — route those to email administration for filter tuning.

Prerequisites

• Access to email gateway logs (Proofpoint, Mimecast, or Microsoft Defender for Office 365)
• Splunk or SIEM with email log ingestion (O365 Message Trace, Exchange tracking logs)
• Sandbox access (Any.Run, Joe Sandbox, or Hybrid Analysis) for URL/attachment detonation
• Microsoft Graph API or Exchange Admin Center for email search and purge operations
• URLScan.io and VirusTotal API keys

Workflow

Step 1: Extract and Analyze Email Headers

Obtain the full email headers (.eml file) from the reported message:

import email
from email import policy

with open("phishing_sample.eml", "rb") as f:
    msg = email.message_from_binary_file(f, policy=policy.default)

# Extract key headers
print(f"From: {msg['From']}")
print(f"Return-Path: {msg['Return-Path']}")
print(f"Reply-To: {msg['Reply-To']}")
print(f"Subject: {msg['Subject']}")
print(f"Message-ID: {msg['Message-ID']}")
print(f"X-Originating-IP: {msg['X-Originating-IP']}")

# Parse Received headers (bottom-up for true origin)
for header in reversed(msg.get_all('Received', [])):
    print(f"Received: {header[:120]}")

# Check authentication results
print(f"Authentication-Results: {msg['Authentication-Results']}")
print(f"DKIM-Signature: {msg.get('DKIM-Signature', 'NONE')[:80]}")

Key checks:

• SPF: Does Return-Path domain match sending IP? Look for spf=pass or