Individual skill
conducting-man-in-the-middle-attack-simulation
Simulates man-in-the-middle attacks using Ettercap, mitmproxy, and Bettercap in authorized environments to intercept, analyze, and modify network traffic for testing encryption enforcement, certificate validation, and detection capabilities.
skills/conducting-man-in-the-middle-attack-simulation/SKILL.md
Source commit 54a798831d2266a3ca61ce68a7acb80b81160d57
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- Observed behavior
- Network or broad shell
- Last checked
- Nov 9, 2026
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- Repository stars (not skill ratings)
- 35,887
- Repository last updated
- Aug 31, 2026
- License
- Apache-2.0
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- ai-agents Repository topic
- claude-code Repository topic
- cybersecurity Repository topic
- incident-response Repository topic
- mitre-attack Repository topic
- penetration-testing Repository topic
- red-team Repository topic
- security Repository topic
- cloud-security Repository topic
- malware-analysis Repository topic
- network-security Declared skill tag
- mitm Declared skill tag
- bettercap Declared skill tag
- ettercap Declared skill tag
- mitmproxy Declared skill tag
- security Derived category
- testing Derived category
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LICENSEasset · 11,255 bytesSKILL.mdcore · 11,805 bytesSKILL.mdcore · 11,805 bytesSKILL.mdcore · 11,805 bytesSKILL.mdcore · 11,805 bytesSKILL.mdcore · 11,805 bytesSKILL.mdcore · 11,805 bytesSKILL.mdcore · 11,805 bytesreferences/api-reference.mddoc · 2,228 bytesscripts/agent.pyruns · 6,574 bytes
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# Conducting Man-in-the-Middle Attack Simulation
## When to Use
- Testing whether applications properly validate TLS certificates and enforce encrypted communications
- Demonstrating the risk of cleartext protocols (HTTP, FTP, Telnet, SMTP) to organization stakeholders
- Validating that HSTS, certificate pinning, and other anti-MITM controls are correctly implemented
- Assessing network detection capabilities for ARP spoofing, DHCP spoofing, and DNS spoofing attacks
- Training incident response teams to identify and respond to MITM attack indicators
**Do not use** on production networks without explicit written authorization and a rollback plan, against systems you do not own or have permission to test, or for intercepting communications of uninvolved third parties.
## Prerequisites
- Written authorization specifying in-scope targets and approved MITM techniques