conducting-spearphishing-simulation-campaign

name	conducting-spearphishing-simulation-campaign
description	Run a targeted spearphishing simulation for initial access by developing OSINT-derived pretexts, building payloads (HTML smuggling, macro docs, ISO/LNK, OneNote, QR codes), standing up look-alike-domain email infrastructure with SPF/DKIM/DMARC via GoPhish, and tracking results. Use in authorized engagements to gain initial access via personalized phishing against specific individuals, distinct from broad campaigns.
domain	cybersecurity
subdomain	red-teaming
tags	["red-team","adversary-simulation","mitre-attack","exploitation","post-exploitation","spearphishing","social-engineering"]
version	1.0
author	mahipal
license	Apache-2.0
d3fend_techniques	["File Metadata Consistency Validation","Application Protocol Command Analysis","Identifier Analysis","Content Format Conversion","Message Analysis"]
nist_csf	["ID.RA-01","GV.OV-02","DE.AE-07"]
mitre_attack	["T1566.001","T1566.002","T1598.003","T1598.002","T1204.002","T1204.001"]
mitre_f3	{"version":"1.1","tactics":["reconnaissance","resource-development","initial-access"],"techniques":[{"id":"T1598","name":"Phishing for Information","tactic":"reconnaissance","source":"attack"},{"id":"T1660","name":"Phishing","tactic":"initial-access","source":"attack"},{"id":"T1583.001","name":"Acquire Infrastructure: Domains","tactic":"resource-development","source":"attack"},{"id":"F1020.002","name":"Create Fake Materials: Fake Website","tactic":"resource-development","source":"f3"},{"id":"T1585","name":"Establish Accounts","tactic":"resource-development","source":"attack"},{"id":"F1006.002","name":"Account Takeover: Exposed Login Credential","tactic":"initial-access","source":"f3"}]}

Conducting Spearphishing Simulation Campaign

Legal Notice: This skill is for authorized security testing and educational purposes only. Unauthorized use against systems you do not own or have written permission to test is illegal and may violate computer fraud laws.

Overview

Spearphishing simulation is a targeted social engineering attack vector used by red teams to gain initial access. Unlike broad phishing campaigns, spearphishing uses OSINT-derived intelligence to craft highly personalized messages targeting specific individuals. This skill covers developing pretexts, building payloads, setting up email infrastructure, executing the campaign, and tracking results.

When to Use

• When conducting security assessments that involve conducting spearphishing simulation campaign
• When following incident response procedures for related security events
• When performing scheduled security testing or auditing activities
• When validating security controls through hands-on testing

Prerequisites

• Familiarity with red teaming concepts and tools
• Access to a test or lab environment for safe execution
• Python 3.8+ with required dependencies installed
• Appropriate authorization for any testing activities

Objectives

• Develop convincing pretexts tailored to specific target personnel
• Create weaponized payloads that bypass email security controls
• Set up email delivery infrastructure with proper SPF/DKIM/DMARC configuration
• Execute phishing campaigns with real-time tracking and metrics
• Document results for engagement reporting and security awareness improvement

MITRE ATT&CK Mapping

• T1566.001 - Phishing: Spearphishing Attachment
• T1566.002 - Phishing: Spearphishing Link
• T1566.003 - Phishing: Spearphishing via Service
• T1598.003 - Phishing for Information: Spearphishing Link
• T1204.001 - User Execution: Malicious Link
• T1204.002 - User Execution: Malicious File
• T1608.001 - Stage Capabilities: Upload Malware
• T1608.005 - Stage Capabilities: Link Target
• T1583.001 - Acquire Infrastructure: Domains
• T1585.002 - Establish Accounts: Email Accounts

Workflow

Phase 1: Pretext Development