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 spf=fail
• DKIM: Is the signature valid? dkim=pass confirms the email was not modified in transit
• DMARC: Does the From domain align with SPF/DKIM domains? dmarc=fail indicates spoofing

Step 2: Analyze URLs and Attachments

URL Analysis:

import requests

# Submit URL to URLScan.io
url_to_scan = "https://evil-login.example.com/office365"
response = requests.post(
    "https://urlscan.io/api/v1/scan/",
    headers={"API-Key": "YOUR_KEY", "Content-Type": "application/json"},
    json={"url": url_to_scan, "visibility": "unlisted"}
)
scan_id = response.json()["uuid"]
print(f"Scan URL: https://urlscan.io/result/{scan_id}/")

# Check VirusTotal for URL reputation
import vt
client = vt.Client("YOUR_VT_API_KEY")
url_id = vt.url_id(url_to_scan)
url_obj = client.get_object(f"/urls/{url_id}")
print(f"VT Score: {url_obj.last_analysis_stats}")
client.close()

Attachment Analysis:

import hashlib

# Calculate file hashes
with open("attachment.docx", "rb") as f:
    content = f.read()
    md5 = hashlib.md5(content).hexdigest()
    sha256 = hashlib.sha256(content).hexdigest()

print(f"MD5: {md5}")
print(f"SHA256: {sha256}")

# Submit to MalwareBazaar for lookup
response = requests.post(
    "https://mb-api.abuse.ch/api/v1/",
    data={"query": "get_info", "hash": sha256}
)
print(response.json()["query_status"])

Submit to sandbox (Any.Run or Joe Sandbox) for dynamic analysis of macros, PowerShell execution, and C2 callbacks.

Step 3: Determine Campaign Scope

Search for all recipients of the same phishing email in Splunk:

index=email sourcetype="o365:messageTrace"
(SenderAddress="attacker@evil-domain.com" OR Subject="Urgent: Password Reset Required"
 OR MessageId="<phishing-message-id@evil.com>")
earliest=-7d
| stats count by RecipientAddress, DeliveryStatus, MessageTraceId
| sort - count

Alternatively, use Microsoft Graph API:

import requests

headers = {"Authorization": f"Bearer {access_token}"}
params = {
    "$filter": f"subject eq 'Urgent: Password Reset Required' and "
               f"receivedDateTime ge 2024-03-14T00:00:00Z",
    "$select": "sender,toRecipients,subject,receivedDateTime",
    "$top": 100
}
response = requests.get(
    "https://graph.microsoft.com/v1.0/users/admin@company.com/messages",
    headers=headers, params=params
)
messages = response.json()["value"]
print(f"Found {len(messages)} matching messages")

Step 4: Identify Impacted Users (Who Clicked)

Check proxy/web logs for users who visited the phishing URL:

index=proxy dest="evil-login.example.com" earliest=-7d
| stats count, values(action) AS actions, latest(_time) AS last_access
  by src_ip, user
| lookup asset_lookup_by_cidr ip AS src_ip OUTPUT owner, category
| sort - count
| table user, src_ip, owner, actions, count, last_access

Check if credentials were submitted (POST requests to phishing domain):

index=proxy dest="evil-login.example.com" http_method=POST earliest=-7d
| stats count by src_ip, user, url, status

Step 5: Containment Actions

Purge emails from all mailboxes:

# Microsoft 365 Compliance Search and Purge
New-ComplianceSearch -Name "Phishing_Purge_2024_0315" `
    -ExchangeLocation All `
    -ContentMatchQuery '(From:attacker@evil-domain.com) AND (Subject:"Urgent: Password Reset Required")'

Start-ComplianceSearch -Identity "Phishing_Purge_2024_0315"

# After search completes, execute purge
New-ComplianceSearchAction -SearchName "Phishing_Purge_2024_0315" -Purge -PurgeType SoftDelete

Block indicators:

• Add sender domain to email gateway block list
• Add phishing URL domain to web proxy block list
• Add attachment hash to endpoint detection block list
• Create DNS sinkhole entry for phishing domain

Reset compromised credentials:

# Force password reset for impacted users
$impactedUsers = @("user1@company.com", "user2@company.com")
foreach ($user in $impactedUsers) {
    Set-MsolUserPassword -UserPrincipalName $user -ForceChangePassword $true
    Revoke-AzureADUserAllRefreshToken -ObjectId (Get-AzureADUser -ObjectId $user).ObjectId
}

Step 6: Document and Report

Create incident report with full timeline, IOCs, impacted users, and remediation actions taken.

| makeresults
| eval incident_id="PHI-2024-0315",
       reported_time="2024-03-15 09:12:00",
       sender="attacker@evil-domain[.]com",
       subject="Urgent: Password Reset Required",
       url="hxxps://evil-login[.]example[.]com/office365",
       recipients_count=47,
       clicked_count=5,
       credentials_submitted=2,
       emails_purged=47,
       passwords_reset=2,
       domains_blocked=1,
       disposition="True Positive - Credential Phishing Campaign"
| table incident_id, reported_time, sender, subject, url, recipients_count,
        clicked_count, credentials_submitted, emails_purged, passwords_reset, disposition

Key Concepts

Term	Definition
SPF (Sender Policy Framework)	DNS TXT record specifying which mail servers are authorized to send on behalf of a domain
DKIM	DomainKeys Identified Mail — cryptographic signature proving email content was not altered in transit
DMARC	Domain-based Message Authentication, Reporting and Conformance — policy combining SPF and DKIM alignment
Credential Harvesting	Phishing technique using fake login pages to capture username/password combinations
Business Email Compromise (BEC)	Social engineering attack using compromised or spoofed executive email for financial fraud
Message Trace	O365/Exchange log showing email routing, delivery status, and filtering actions for forensic analysis

Tools & Systems

• Microsoft Defender for Office 365: Email security platform with Safe Links, Safe Attachments, and Threat Explorer for investigation
• URLScan.io: Free URL analysis service capturing screenshots, DOM, cookies, and network requests
• Any.Run: Interactive sandbox for detonating malicious files and URLs with real-time behavior analysis
• Proofpoint TAP: Targeted Attack Protection dashboard showing clicked URLs and delivered threats per user
• PhishTool: Dedicated phishing email analysis platform automating header parsing and IOC extraction

Common Scenarios

• Credential Phishing: Fake O365 login page — check proxy for POST requests, force password resets for submitters
• Macro-Enabled Document: Word doc with VBA macro — sandbox shows PowerShell download cradle, check endpoints for execution
• QR Code Phishing (Quishing): Email contains QR code linking to credential harvester — decode QR, submit URL to sandbox
• Thread Hijacking: Attacker uses compromised mailbox to reply in existing threads — check for impossible travel or new inbox rules
• Voicemail Phishing: Fake voicemail notification with HTML attachment — analyze attachment for redirect chains

Output Format

PHISHING INCIDENT REPORT — PHI-2024-0315
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
Reported:     2024-03-15 09:12 UTC by jsmith (Finance)
Sender:       attacker@evil-domain[.]com (SPF: FAIL, DKIM: NONE, DMARC: FAIL)
Subject:      Urgent: Password Reset Required
Payload:      Credential harvesting URL

IOCs:
  URL:        hxxps://evil-login[.]example[.]com/office365
  Domain:     evil-login[.]example[.]com (registered 2024-03-14, Namecheap)
  IP:         185.234.xx.xx (VT: 12/90 malicious)

Scope:
  Recipients: 47 users across Finance and HR departments
  Clicked:    5 users visited phishing URL
  Submitted:  2 users entered credentials (confirmed via POST in proxy logs)

Containment:
  [DONE] 47 emails purged via Compliance Search
  [DONE] Domain blocked on proxy and DNS sinkhole
  [DONE] 2 user passwords reset, sessions revoked
  [DONE] MFA enforced for both compromised accounts
  [DONE] Inbox rules audited — no forwarding rules found

Status:       RESOLVED — No evidence of lateral movement post-compromise

Verification Criteria

Confirm successful execution by validating:

• [ ] All prerequisite tools and access requirements are satisfied
• [ ] Each workflow step completed without errors
• [ ] Output matches expected format and contains expected data
• [ ] No security warnings or misconfigurations detected
• [ ] Results are documented and evidence is preserved for audit

Compliance Framework Mapping

This skill supports compliance evidence collection across multiple frameworks:

• SOC 2: CC7.1 (Monitoring), CC7.2 (Anomaly Detection), CC7.3 (Incident Identification)
• ISO 27001: A.12.4 (Logging & Monitoring), A.16.1 (Security Incident Management)
• NIST 800-53: AU-6 (Audit Review), SI-4 (System Monitoring), IR-5 (Incident Monitoring)
• NIST CSF: DE.AE (Anomalies & Events), DE.CM (Continuous Monitoring)

Claw GRC Tip: When this skill is executed by a registered agent, compliance evidence is automatically captured and mapped to the relevant controls in your active frameworks.

Deploying This Skill with Claw GRC

Agent Execution

Register this skill with your Claw GRC agent for automated execution:

# Install via CLI
npx claw-grc skills add investigating-phishing-email-incident

# Or load dynamically via MCP
grc.load_skill("investigating-phishing-email-incident")

Audit Trail Integration

When executed through Claw GRC, every step of this skill generates tamper-evident audit records:

• SHA-256 chain hashing ensures no step can be modified after execution
• Evidence artifacts (configs, scan results, logs) are automatically attached to relevant controls
• Trust score impact — successful execution increases your agent's trust score

Continuous Compliance

Schedule this skill for recurring execution to maintain continuous compliance posture. Claw GRC monitors for drift and alerts when re-execution is needed.