performing-ssl-tls-inspection-configuration

name	performing-ssl-tls-inspection-configuration
description	Configure SSL/TLS inspection on network security devices to decrypt, inspect, and re-encrypt HTTPS traffic for threat detection while managing certificates, exemptions, and privacy compliance.
domain	cybersecurity
subdomain	network-security
tags	["ssl-inspection","tls-decryption","https-inspection","certificate-management","proxy","man-in-the-middle","network-security","forward-proxy"]
version	1.0
author	mahipal
license	Apache-2.0
nist_csf	["PR.IR-01","DE.CM-01","ID.AM-03","PR.DS-02"]
mitre_attack	["T1046","T1040","T1557","T1071","T1573"]
source	https://github.com/mukul975/Anthropic-Cybersecurity-Skills
source_commit	04450304b12645cb2b974ab96d28c0664758a88d

Performing SSL/TLS Inspection Configuration

Overview

SSL/TLS inspection (also called SSL decryption, HTTPS inspection, or TLS break-and-inspect) intercepts encrypted traffic between clients and servers to inspect the cleartext content for malware, data exfiltration, policy violations, and command-and-control communications. The inspection device acts as a trusted man-in-the-middle, terminating the TLS session from the client, inspecting the plaintext content, and establishing a new TLS session to the destination server. With over 95% of web traffic now encrypted, organizations without TLS inspection have a massive blind spot. This skill covers configuring TLS inspection on next-generation firewalls, deploying trusted CA certificates, managing exemptions for certificate-pinned applications, and ensuring compliance with privacy regulations.

When to Use

• When conducting security assessments that involve performing ssl tls inspection configuration
• 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

• Next-generation firewall or secure web gateway with TLS inspection capability
• Internal Certificate Authority (CA) for signing inspection certificates
• Endpoint certificate management (GPO, MDM, or manual deployment)
• Privacy and legal review for TLS inspection scope
• Understanding of PKI, X.509 certificates, and TLS handshake

Core Concepts

SSL/TLS Inspection Modes

Mode	Direction	Description
SSL Forward Proxy	Outbound	Intercepts client-to-internet HTTPS connections
SSL Inbound Inspection	Inbound	Decrypts traffic destined for internal servers
SSH Proxy	Both	Inspects SSH tunneled traffic

Forward Proxy Process

Client                  Firewall/Proxy              Web Server
  │                         │                          │
  │──TLS ClientHello──────→│                          │
  │                         │──TLS ClientHello───────→│
  │                         │←─TLS ServerHello────────│
  │                         │  (real server cert)      │
  │                         │                          │
  │                         │  [Validates server cert]  │
  │                         │  [Generates proxy cert   │
  │                         │   signed by internal CA]  │
  │                         │                          │
  │←─TLS ServerHello───────│                          │
  │  (proxy-signed cert)    │                          │
  │                         │                          │
  │──Encrypted data────────→│  [Decrypt, Inspect]      │
  │                         │──Encrypted data────────→│
  │←─Encrypted data─────────│  [Decrypt, Inspect]      │
  │                         │←─Encrypted data─────────│