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350-701 Practice Question: A company has a site-to-site VPN between two ASA…

A company has a site-to-site VPN between two ASA firewalls using IKEv2. The tunnel was working but after an upgrade, it fails. The engineer verifies that the pre-shared keys match, IKE proposals are compatible, and the crypto ACL is correctly defined. What is the next likely cause to investigate?

⚠ Common exam trap

Cisco often tests the misconception that post-upgrade failures are always due to configuration mismatches, but the trap here is that intermediate firewall rules or ACL changes are frequently overlooked after an upgrade, even when all other parameters are verified as correct.

Answer choices

Why each option matters

Answer the question above first, then reveal the full breakdown to understand why each option is right or wrong.

Correct answer & explanation

The firewall rules on the intermediate devices are blocking ISAKMP traffic.

The tunnel was working before the upgrade and the engineer has already verified that the pre-shared keys, IKE proposals, and crypto ACL are correct. After an ASA upgrade, intermediate firewall rules or ACLs may be reset or changed, potentially blocking ISAKMP (UDP 500/4500) traffic. Since the tunnel fails to establish, the next logical step is to check if ISAKMP traffic is being permitted through all intermediate devices, as this is a common post-upgrade issue.

Answer analysis

Option-by-option breakdown

For each option: why learners choose it and why it is or isn't the right answer here.

  • The firewall rules on the intermediate devices are blocking ISAKMP traffic.

    Why this is correct

    Intermediate firewall changes during upgrade can block UDP ports 500 and 4500, preventing IKE negotiation. This is a common cause.

  • The ACL for interesting traffic is missing.

    Why it's wrong here

    If the crypto ACL were missing, the tunnel would not have been triggered. But since it was working, it's likely still present.

  • The crypto map is not applied to the correct interface.

    Why it's wrong here

    If the crypto map were not applied, the tunnel would not have been working before the upgrade. Since it was working, the map application is likely correct.

  • The MTU is too high.

    Why it's wrong here

    MTU issues can cause problems but typically affect traffic after tunnel is up, not tunnel establishment.

Visual reference

Source Router + ACL permit 10.0.0.0/8 deny any Server 10.0.0.5 ✓ 192.168.1.1 ✗ dropped ACLs evaluate top-down; first match wins — implicit deny all at end

Quick reference

VPN Protocol Comparison

ProtocolPortEncryptionAuthenticationUse Case
IKEv2 / IPsecUDP 500 / 4500AES-256Certificates / PSKSite-to-site & remote access
SSL / TLS VPNTCP 443TLS 1.3Certificates / MFAClientless remote access
L2TP / IPsecUDP 1701AES (IPsec)PSK / CertificatesLegacy remote access
WireGuardUDP 51820ChaCha20Public keysModern high-performance VPN
PPTPTCP 1723MPPE (weak)MS-CHAPv2Legacy — avoid in production

PPTP is considered insecure. IKEv2/IPsec and SSL VPN are the current recommended options.

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Written by Johnson Ajibi, MSc IT Security

Senior Network & Security Engineer · founder of Courseiva

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