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EC-Council

312-49 · Question #396

After passing her CEH exam, Carol wants to ensure that her network is completely secure. She implements a DMZ, statefull firewall, NAT, IPSEC, and a packet filtering firewall. Since all security measu

The correct answer is C. NAT does not work with IPSEC. NAT modifies IP headers by rewriting source/destination addresses (and sometimes ports), which fundamentally conflicts with IPSec. IPSec's Authentication Header (AH) mode creates a cryptographic hash that covers the entire IP packet including headers; any NAT modification invalid

Submitted by dimitri_ru· Apr 18, 2026Network Forensics

Question

After passing her CEH exam, Carol wants to ensure that her network is completely secure. She implements a DMZ, statefull firewall, NAT, IPSEC, and a packet filtering firewall. Since all security measures were taken, none of the hosts on her network can reach the Internet. Why is that?

Options

  • AIPSEC does not work with packet filtering firewalls
  • BStatefull firewalls do not work with packet filtering firewalls
  • CNAT does not work with IPSEC
  • DNAT does not work with statefull firewalls

How the community answered

(30 responses)
  • A
    17% (5)
  • B
    7% (2)
  • C
    73% (22)
  • D
    3% (1)

Explanation

NAT modifies IP headers by rewriting source/destination addresses (and sometimes ports), which fundamentally conflicts with IPSec. IPSec's Authentication Header (AH) mode creates a cryptographic hash that covers the entire IP packet including headers; any NAT modification invalidates that hash and causes the packet to be rejected. Even ESP mode is problematic because TCP/UDP ports may be encrypted, preventing NAT from performing port address translation. The solution is NAT-T (NAT Traversal, RFC 3947), which encapsulates IPSec packets inside UDP port 4500 to allow them to traverse NAT devices.

Topics

#NAT#IPSEC#Network Security Protocols#Firewall Configuration

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