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.
internal/tools/skills/data/network-security/conducting-man-in-the-middle-attack-simulation/SKILL.md
Source commit d42f381ad34843e71a42658e5c57290c713e85af
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- Yes
- Scanner rules are current
- Yes
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- No
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- Observed behavior
- Network or broad shell
- Last checked
- Nov 9, 2026
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- Repository stars (not skill ratings)
- 1,319
- Repository last updated
- Nov 8, 2026
- License
- Apache-2.0
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- cybersecurity Repository topic
- security Repository topic
- bug-bounty Repository topic
- automation Repository topic
- autonomous-pentesting Repository topic
- ai-agent Repository topic
- ai-security Repository topic
- ethical-hacking Repository topic
- golang Repository topic
- penetration-testing 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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# 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.
## Most Often Missed & How to Confirm
- **IPv6 and DHCPv6 paths:** teams ARP-spoof IPv4 and miss that hosts prefer IPv6. Run `bettercap`'s `dhcp6.spoof`/SLAAC RA spoofing too; positive signal is the victim sending traffic to your link-local address. Don't conclude "MITM blocked" until you've tried the IPv6 default route.