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Security+ Academy · Lesson

SSL/TLS Inspection and Man-in-the-Browser Attacks

Learn when and how to inspect encrypted HTTPS traffic on security gateways, and explore how browser-based attacks like SSL stripping and malicious extensions work.

Why Inspect Encrypted Traffic?

HTTPS now accounts for more than 90% of web traffic — including malware downloads, C2 channels, and data exfiltration. Perimeter security tools that cannot inspect TLS see only encrypted blobs, creating a blind spot that attackers actively exploit. SSL/TLS inspection (also called SSL interception, SSL bumping, or deep packet inspection for HTTPS) allows security gateways to decrypt, inspect, and re-encrypt HTTPS traffic before it reaches the endpoint. This visibility is essential for web content filtering, DLP, and anti-malware scanning in environments where most traffic is HTTPS.

How SSL/TLS Inspection Works

SSL inspection is technically a controlled man-in-the-middle performed by the organization's own security infrastructure. The process: Step 1: Client establishes TLS to the proxy (using the proxy's certificate signed by the corporate CA). Step 2: Proxy establishes a separate TLS session to the actual server using the server's real certificate. Step 3: Proxy decrypts traffic from the client, inspects it, then re-encrypts and forwards it to the server (and vice versa). The client trusts the proxy's certificate because the corporate CA certificate is pre-installed on all managed endpoints via MDM or Group Policy.

# SSL inspection flow
Client                  Proxy (SEG)           Real Server
  |                        |                       |
  |--TLS ClientHello------>|                       |
  |  (proxy cert presented)|                       |
  |<-TLS Established-------|--TLS ClientHello----->|
  |                        |<-TLS Established------|
  |--HTTPS Request-------->|                       |
  |                        |--HTTPS Request------->|
  |                        |<-HTTPS Response-------|
  |  (inspect, DLP, AV)    |                       |
  |<-HTTPS Response--------|                       |
  |                        |                       |

All lessons in this course

  1. Email Authentication: SPF, DKIM, and DMARC
  2. Secure Email Gateways and Anti-Spam Controls
  3. Web Content Filtering and DNS Sinkholes
  4. SSL/TLS Inspection and Man-in-the-Browser Attacks
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