IPsec VPN – Concepts & Protocols

1. What Is IPsec and Why Is It Used?

IPsec (Internet Protocol Security) is a suite of open-standard protocols defined primarily in RFC 4301 that provides authentication, integrity, and confidentiality for IP packets at Layer 3. Unlike application-layer security solutions (TLS, SSH), IPsec operates at the network layer — it can protect any IP traffic regardless of the application above it, making it ideal for securing entire communication channels between networks or devices.

IPsec is the foundation of site-to-site VPNs — encrypted tunnels that connect branch offices to headquarters or cloud environments over untrusted public networks such as the internet. It is also used in remote-access VPNs (often via IKEv2 or L2TP/IPsec) and as the underlying security layer for protocols like DMVPN and GRE over IPsec.

IPsec Service What It Provides Protocol Responsible
Confidentiality Encrypts packet payload so intercepted traffic cannot be read ESP (Encapsulating Security Payload)
Data Integrity Detects any modification to packets in transit using a hash (HMAC) ESP and AH (Authentication Header)
Origin Authentication Verifies the packet came from the expected peer (pre-shared key or digital certificate) IKE (Internet Key Exchange) + ESP/AH
Anti-Replay Protection Uses sequence numbers to detect and discard duplicate or replayed packets ESP and AH
Key Management Securely negotiates and refreshes encryption keys without manual intervention IKE / ISAKMP

Related pages: IPsec Basics | Site-to-Site vs Remote-Access VPN | GRE Tunnels | DMVPN Overview | Firewall Overview | ACL Overview | WAN Technologies | Common Port Numbers (IKE UDP 500) | Site-to-Site IPsec VPN Lab

2. IPsec Protocol Suite Overview

IPsec is not a single protocol — it is a framework composed of multiple protocols that each handle a specific aspect of secure communication. The two core data-protection protocols are ESP and AH. Key management is handled by IKE. The framework also defines the concept of Security Associations (SAs) to describe negotiated security parameters.

Component Protocol / RFC Role
AH – Authentication Header IP Protocol 51 / RFC 4302 Provides integrity and authentication for the entire IP packet (including the outer IP header); does NOT encrypt payload
ESP – Encapsulating Security Payload IP Protocol 50 / RFC 4303 Provides encryption, integrity, and authentication for the payload; does NOT protect the outer IP header
IKE – Internet Key Exchange UDP port 500 (IKEv1/v2) / RFC 7296 Negotiates Security Associations, exchanges keys, authenticates peers before data flow begins
ISAKMP – Internet Security Association and Key Management Protocol UDP port 500 / RFC 2408 Framework used by IKEv1 to define message formats and exchange types for SA negotiation
SA – Security Association RFC 4301 A one-way agreement on the security parameters (algorithm, key, SPI) to use for a protected flow. Two SAs are required for bidirectional traffic.

3. ESP vs AH – Detailed Comparison

The choice between ESP and AH is one of the most commonly tested IPsec topics. In practice, ESP is used in almost all modern deployments because it provides both encryption and integrity. AH is rarely deployed today, but you must understand what it does and when it cannot be used.

Feature ESP (Protocol 50) AH (Protocol 51)
Encryption (Confidentiality) ✔ Yes — encrypts the payload using symmetric algorithms (AES, 3DES) ✘ No — AH provides no encryption whatsoever
Data Integrity ✔ Yes — HMAC covers the ESP header + payload + ESP trailer ✔ Yes — HMAC covers the entire IP packet including the outer IP header
Origin Authentication ✔ Yes ✔ Yes
Anti-Replay Protection ✔ Yes — sequence number field in ESP header ✔ Yes — sequence number field in AH header
Outer IP header protection ✘ No — outer IP header is in cleartext and is not authenticated ✔ Yes — HMAC covers the outer IP header (immutable fields)
NAT compatibility ✔ Compatible with NAT when using NAT-T (NAT Traversal — ESP is encapsulated in UDP port 4500) ✘ Incompatible with NAT — NAT changes the outer IP header, breaking AH's integrity check
IP Protocol number 50 51
Modern usage Standard choice — used in virtually all IPsec deployments Rarely used — mainly where outer header integrity is a strict requirement and no NAT exists

3.1 ESP Packet Structure

Field Size Description
SPI (Security Parameter Index) 4 bytes Identifies which Security Association applies to this packet
Sequence Number 4 bytes Monotonically increasing counter — enables anti-replay detection
Payload Data (encrypted) Variable The protected content — original IP packet (tunnel mode) or original transport-layer segment (transport mode)
Padding 0–255 bytes Aligns payload to block cipher boundary
Pad Length 1 byte Number of padding bytes added
Next Header 1 byte Protocol of the payload (e.g., 4 = IPv4, 41 = IPv6, 6 = TCP, 17 = UDP)
ICV (Integrity Check Value) Variable (12–32 bytes) HMAC authentication tag — covers SPI, Sequence Number, and encrypted payload; appended at the end of the ESP packet

4. Tunnel Mode vs Transport Mode

IPsec can operate in two modes that determine what portion of the original packet is protected and how the new IPsec packet is structured.

Feature Tunnel Mode Transport Mode
What is protected The entire original IP packet (header + payload) is encapsulated and encrypted inside a new outer IP packet Only the payload (transport layer and above) of the original packet is protected; the original IP header is retained
New outer IP header ✔ Yes — added by the IPsec gateway; source/destination are the gateway endpoints, not the original hosts ✘ No — the original IP header is used as the outer header; only an ESP/AH header is inserted after it
Original IP header visibility Hidden — encrypted inside the ESP payload Visible — original source and destination IPs are in cleartext
Overhead Higher — adds a new outer IP header (20 bytes minimum) Lower — no new IP header, only ESP/AH header added
Typical use case Site-to-site VPNs — the IPsec gateway protects traffic on behalf of entire subnets. End hosts are unaware of IPsec. Host-to-host encryption — both endpoints run IPsec themselves (e.g., two servers communicating directly)
NAT traversal Supported with NAT-T (ESP in UDP 4500) More limited — original IPs must be routable
CCNA relevance Primary focus — site-to-site IPsec VPN uses tunnel mode Awareness only for CCNA; more relevant in advanced security

4.1 Tunnel Mode Packet Structure (ESP)

Layer / Field Content Encrypted?
New Outer IP Header Source = VPN gateway A IP; Destination = VPN gateway B IP No — in cleartext for routing
ESP Header SPI + Sequence Number No — needed for SA lookup and anti-replay
Original IP Header Source = Host A IP; Destination = Host B IP Yes — encrypted by ESP
Original Payload TCP/UDP segment, application data Yes — encrypted by ESP
ESP Trailer + ICV Padding, Next Header, Authentication tag Trailer encrypted; ICV in cleartext

5. Security Associations (SAs)

A Security Association (SA) is a one-way logical connection that defines all the parameters two IPsec peers have agreed to use for a protected data flow. Because an SA is unidirectional, two SAs are required for bidirectional communication — one for inbound traffic and one for outbound traffic.

SA Parameter Description
SPI (Security Parameter Index) A 32-bit value in the ESP/AH header that uniquely identifies the SA to apply to an incoming packet. The receiving peer uses the SPI to look up the correct SA in its Security Association Database (SAD).
Destination IP address The endpoint this SA applies to — combined with the SPI and protocol, uniquely identifies the SA
Protocol (ESP or AH) Which IPsec protocol the SA uses
Encryption algorithm & key e.g., AES-256; the symmetric key used for encryption (ESP only)
Integrity algorithm & key e.g., HMAC-SHA-256; the key used for the authentication tag
Lifetime How long the SA is valid — either in time (seconds) or data volume (kilobytes); SA is renegotiated before expiry
Mode Tunnel or transport
Sequence number counter Used for anti-replay; starts at 1 and increments with each packet

SAs are stored in the Security Association Database (SAD). The rules for which traffic should be protected are stored in the Security Policy Database (SPD).

6. IKE – Internet Key Exchange

IKE (Internet Key Exchange) is the protocol responsible for automatically negotiating Security Associations, authenticating peers, and exchanging cryptographic keys before IPsec data traffic can flow. Without IKE, all keys and SA parameters would have to be manually configured on every device — impractical at any scale.

IKE operates in two versions: IKEv1 (the original, more complex) and IKEv2 (RFC 7296 — simpler, faster, more secure, and the modern standard). Both use UDP port 500 (see Common Port Numbers). When NAT is detected between peers, IKE switches to UDP port 4500 (NAT Traversal).

Feature IKEv1 IKEv2
RFC RFC 2409 (IKE) + RFC 2408 (ISAKMP) RFC 7296
Message exchanges to establish SA Phase 1: 9 messages (main mode) or 6 (aggressive mode); Phase 2: 3 messages 4 messages total (initial exchange)
Authentication methods Pre-shared keys, RSA signatures, RSA encryption Pre-shared keys, digital certificates, EAP (supports more methods)
Built-in NAT traversal Extension (RFC 3947) Built-in natively
MOBIKE support No Yes — allows VPN to survive IP address changes (mobile clients)
Reliability No built-in reliability — exchanges can fail silently Built-in request/response with retransmission
CCNA focus IKEv1 concepts (Phase 1/Phase 2) are primary CCNA exam topic Awareness at CCNA level; IKEv2 is the modern standard

7. IKE Phase 1 – Building the Management Tunnel

IKE Phase 1 establishes a secure, authenticated channel between two IPsec peers — called the ISAKMP SA or IKE SA. This management tunnel protects all subsequent IKE Phase 2 negotiations. Phase 1 does not carry any data traffic — it is purely for key exchange and peer authentication.

7.1 Phase 1 Negotiation Parameters (ISAKMP Policy)

Both peers must agree on the same set of Phase 1 parameters. On Cisco IOS, these are defined in an ISAKMP policy:

Parameter Options Notes
Encryption algorithm AES-128, AES-192, AES-256, 3DES, DES Protects the Phase 1 exchange itself; AES-256 recommended
Hash / Integrity algorithm SHA-256, SHA-384, SHA-512, SHA-1, MD5 HMAC used for integrity verification; SHA-256+ recommended
Authentication method Pre-shared key (PSK), RSA signatures (digital certificates) PSK is simpler; certificates scale better in large deployments. For device AAA authentication see AAA TACACS+/RADIUS Configuration
Diffie-Hellman group Group 14 (2048-bit), Group 19 (256-bit ECC), Group 20 (384-bit ECC), Group 24 (2048-bit + PFS), older: Group 1, 2, 5 DH group determines the strength of the key exchange; Group 14+ is the minimum recommended today
Lifetime Default: 86,400 seconds (24 hours) How long the Phase 1 SA remains valid before renegotiation

7.2 Phase 1 Modes (IKEv1)

Mode Messages Identity Protection Use Case
Main Mode 6 messages (3 exchanges of 2) ✔ Yes — peer identities are encrypted Site-to-site VPNs with static IP addresses — more secure
Aggressive Mode 3 messages ✘ No — identities exchanged in cleartext Remote-access VPNs with dynamic IP peers — faster but less secure

7.3 Diffie-Hellman Key Exchange

Diffie-Hellman (DH) is the public-key algorithm IPsec uses to allow two peers to derive a shared secret key over an untrusted network without ever transmitting the key itself. Each peer generates a public/private key pair, exchanges public keys, and independently computes the same shared secret — which is then used to derive the symmetric encryption keys for the Phase 1 SA.

The DH group number specifies the mathematical group (and therefore key length) used. Higher group numbers provide stronger security but require more CPU. Groups 1, 2, and 5 are considered weak by modern standards and should not be used in new deployments.

8. IKE Phase 2 – Building the Data Tunnel

IKE Phase 2 runs inside the secure Phase 1 tunnel and negotiates the IPsec SAs — the actual security parameters used to protect data traffic. Phase 2 uses a single mode called Quick Mode which exchanges 3 messages. The result is a pair of unidirectional IPsec SAs (one in each direction) that define how data packets will be encrypted and authenticated.

8.1 Phase 2 Negotiation Parameters (Transform Set)

On Cisco IOS, Phase 2 parameters are defined in a transform set — a named combination of the IPsec protocol and algorithms to use:

Parameter Options Notes
IPsec protocol ESP, AH, or ESP+AH ESP is almost always used; AH rarely; combined mode uncommon
Encryption algorithm (ESP) AES-128, AES-192, AES-256, 3DES, DES, NULL (no encryption) AES-256 recommended; NULL = integrity without confidentiality
Integrity / Authentication algorithm HMAC-SHA-256, HMAC-SHA-384, HMAC-SHA-512, HMAC-SHA-1, HMAC-MD5 SHA-256+ recommended; MD5 and SHA-1 are considered weak
Mode Tunnel or Transport Tunnel mode for site-to-site; Transport for host-to-host
Lifetime Default: 3,600 seconds (1 hour) and/or 4,608,000 KB Shorter than Phase 1 lifetime — Phase 2 SAs are renegotiated more frequently for forward secrecy
PFS (Perfect Forward Secrecy) Optional — specifies a new DH group for Phase 2 key derivation If enabled, a fresh DH exchange occurs during every Phase 2 renegotiation — compromise of one session key does not expose others

8.2 Phase 1 vs Phase 2 Summary

Aspect IKE Phase 1 IKE Phase 2
Purpose Establish a secure management channel (ISAKMP SA) for Phase 2 negotiation Negotiate IPsec SAs for protecting actual data traffic
Cisco config object ISAKMP policy (crypto isakmp policy) Transform set (crypto ipsec transform-set)
SA name ISAKMP SA / IKE SA IPsec SA
IKEv1 mode Main Mode or Aggressive Mode Quick Mode
Default lifetime 86,400 seconds (24 hours) 3,600 seconds (1 hour)
Traffic protected IKE negotiation messages only Actual user data (the VPN traffic)
Number of SAs created 1 bidirectional ISAKMP SA 2 unidirectional IPsec SAs (one inbound, one outbound)

9. Site-to-Site IPsec VPN – End-to-End Flow

Putting it all together, here is the complete sequence of events when a site-to-site IPsec VPN is established between two branch offices connected over the internet:

Step Event Protocol
1 Host A at Site 1 sends a packet destined for Host B at Site 2. The packet matches the crypto ACL (interesting traffic — see ACL Overview) on Router 1 — IPsec is triggered. IP routing
2 Router 1 initiates IKE Phase 1 with Router 2. Both peers exchange ISAKMP policy proposals. They agree on encryption, hash, authentication method, and DH group. IKE / ISAKMP (UDP 500)
3 Diffie-Hellman exchange occurs — both routers compute the same shared secret without transmitting it. Session keys are derived from the DH shared secret. IKE / DH
4 Peer authentication — each router verifies the other's identity using the pre-shared key or digital certificate. IKE (PSK or PKI)
5 Phase 1 completes — the ISAKMP SA (bidirectional secure management channel) is established. IKE
6 Router 1 initiates IKE Phase 2 (Quick Mode) inside the Phase 1 tunnel. Both peers negotiate the transform set (ESP algorithm, integrity algorithm, mode, lifetime, PFS). IKE Phase 2 (inside ISAKMP SA)
7 Phase 2 completes — two unidirectional IPsec SAs are created: one for Router 1 → Router 2 traffic, one for Router 2 → Router 1 traffic. IKE Phase 2
8 The original packet from Host A is encapsulated in ESP tunnel mode: the original IP packet becomes the encrypted payload of a new packet with outer IP header (Router 1 public IP → Router 2 public IP). ESP (IP Protocol 50)
9 Router 2 receives the ESP packet, looks up the SA using the SPI, decrypts and verifies integrity, strips the ESP encapsulation, and delivers the original packet to Host B. ESP
10 When the Phase 2 SA lifetime expires, a new Phase 2 is negotiated automatically (without user disruption) using the still-active Phase 1 SA. IKE Phase 2 renegotiation

10. Cisco IOS IPsec VPN Configuration Overview

A site-to-site IPsec VPN on Cisco IOS (IKEv1 / crypto map method) requires five configuration components. The following is a conceptual overview — see the Site-to-Site IPsec VPN Lab for the full step-by-step configuration, and GRE Tunnels if you also need to carry dynamic routing protocols (OSPF/EIGRP) over the VPN.

10.1 Step 1 – Define the ISAKMP Policy (Phase 1)

Router(config)# crypto isakmp policy 10
Router(config-isakmp)# encryption aes 256
Router(config-isakmp)# hash sha256
Router(config-isakmp)# authentication pre-share
Router(config-isakmp)# group 14
Router(config-isakmp)# lifetime 86400
Router(config-isakmp)# exit

! Set the pre-shared key for the remote peer
Router(config)# crypto isakmp key SECRETKEY123 address 203.0.113.2

10.2 Step 2 – Define the Transform Set (Phase 2)

! Name the transform set and specify ESP with AES-256 encryption and SHA-256 integrity
Router(config)# crypto ipsec transform-set MYSET esp-aes 256 esp-sha256-hmac
Router(cfg-crypto-trans)# mode tunnel
Router(cfg-crypto-trans)# exit

10.3 Step 3 – Define Interesting Traffic (Crypto ACL)

! Identify which traffic should be encrypted (site 1 subnet to site 2 subnet)
Router(config)# ip access-list extended VPN_TRAFFIC
Router(config-ext-nacl)# permit ip 192.168.1.0 0.0.0.255 10.0.2.0 0.0.0.255
Router(config-ext-nacl)# exit

10.4 Step 4 – Create the Crypto Map

! Bind the ISAKMP policy, transform set, and ACL together, pointing to the remote peer
Router(config)# crypto map MYMAP 10 ipsec-isakmp
Router(config-crypto-map)# set peer 203.0.113.2
Router(config-crypto-map)# set transform-set MYSET
Router(config-crypto-map)# match address VPN_TRAFFIC
Router(config-crypto-map)# set pfs group14
Router(config-crypto-map)# exit

10.5 Step 5 – Apply Crypto Map to the Outside Interface

! Apply to the interface facing the internet / untrusted network
Router(config)# interface GigabitEthernet0/0
Router(config-if)# crypto map MYMAP
Router(config-if)# exit

11. IPsec VPN Verification Commands

Command Output / Purpose
show crypto isakmp sa Phase 1 ISAKMP SAs — state (QM_IDLE = active), peer IP, and lifetime remaining. QM_IDLE means Phase 1 is up and Phase 2 negotiation can proceed.
show crypto ipsec sa Phase 2 IPsec SAs — inbound and outbound SAs per peer, SPI values, encap/decap packet counts, encryption algorithm, and lifetime
show crypto isakmp policy Lists all configured ISAKMP policies with their priority, encryption, hash, auth method, DH group, and lifetime
show crypto ipsec transform-set Lists all configured transform sets — protocol, algorithms, and mode
show crypto map Shows all crypto maps — peer address, transform set, ACL, and which interface the map is applied to
show crypto engine connections active Currently active IPsec connections and packet counts; useful for confirming traffic is being encrypted
debug crypto isakmp Real-time Phase 1 negotiation messages — shows policy matching, DH exchange, and authentication events. Use with caution in production.
debug crypto ipsec Real-time Phase 2 negotiation and ESP encapsulation/decapsulation events
clear crypto isakmp Clears all Phase 1 ISAKMP SAs — forces renegotiation; also clears dependent Phase 2 SAs
clear crypto sa Clears all IPsec SAs — forces Phase 2 renegotiation without clearing Phase 1

12. IPsec VPN Quick-Reference Summary

IPsec Concept Key Fact
Framework RFC RFC 4301
Operating layer Layer 3 (Network layer)
ESP protocol number IP Protocol 50
AH protocol number IP Protocol 51
ESP provides Encryption + Integrity + Anti-replay (does NOT protect outer IP header)
AH provides Integrity + Anti-replay + outer IP header protection (NO encryption)
AH + NAT Incompatible — NAT breaks AH's outer header integrity check
Tunnel mode Entire original IP packet encrypted — new outer header added; used for site-to-site VPNs
Transport mode Only payload encrypted — original IP header retained; used for host-to-host
IKE port UDP 500 (NAT-T uses UDP 4500)
IKE Phase 1 purpose Establish ISAKMP SA — secure management channel for Phase 2
IKE Phase 1 Cisco config crypto isakmp policy <priority>
IKE Phase 1 default lifetime 86,400 seconds (24 hours)
IKE Phase 2 purpose Negotiate IPsec SAs for data encryption
IKE Phase 2 Cisco config crypto ipsec transform-set
IKE Phase 2 default lifetime 3,600 seconds (1 hour)
SAs needed per direction 1 SA per direction = 2 IPsec SAs for bidirectional traffic
DH purpose Securely derive shared secret key without transmitting it
Verify Phase 1 show crypto isakmp sa
Verify Phase 2 show crypto ipsec sa

Test Your Knowledge – IPsec VPN Quiz

1. Which IPsec protocol provides both encryption AND data integrity, and what is its IP protocol number?

Correct answer is C. ESP (IP Protocol 50) is the workhorse of IPsec — it provides encryption (confidentiality), data integrity via HMAC, origin authentication, and anti-replay protection. AH (Protocol 51) provides integrity and authentication but NO encryption. ESP is used in virtually all modern IPsec deployments.

2. Why is AH incompatible with NAT?

Correct answer is D. AH authenticates the entire IP packet including the outer IP header's source address. When a NAT device translates the source IP address, the HMAC calculated over the original packet no longer matches — the receiving IPsec peer discards the packet as tampered. ESP does not have this problem because it does not authenticate the outer IP header; NAT-T encapsulates ESP in UDP 4500 for additional compatibility.

3. What is the key difference between IPsec tunnel mode and transport mode?

Correct answer is B. In tunnel mode, the entire original IP packet (header + payload) is encrypted and becomes the payload of a new packet with a new outer IP header containing the VPN gateway addresses. This hides the original source and destination IPs. In transport mode, only the transport-layer payload is encrypted; the original IP header remains in cleartext. Tunnel mode is used for site-to-site VPNs; transport mode for host-to-host IPsec.

4. What is the purpose of IKE Phase 1 in an IPsec VPN establishment?

Correct answer is A. IKE Phase 1 creates the ISAKMP SA — a bidirectional secure channel between the two IPsec peers. This management tunnel protects the Phase 2 negotiation that follows. Phase 1 involves: agreeing on algorithms (encryption, hash, DH group), performing the Diffie-Hellman exchange, and authenticating each peer's identity. Phase 1 carries no data traffic itself.

5. What does a Cisco IOS transform set define in an IPsec configuration?

Correct answer is C. A transform set (configured with crypto ipsec transform-set) defines the Phase 2 parameters: which IPsec protocol to use (ESP, AH), which encryption algorithm (AES-256, 3DES), which integrity/authentication algorithm (HMAC-SHA-256), and the mode (tunnel or transport). The ISAKMP policy defines Phase 1 parameters separately.

6. How many IPsec SAs are required for bidirectional traffic between two VPN peers, and why?

Correct answer is B. A Security Association is a one-way agreement — it only defines the parameters for traffic flowing in a single direction. To protect traffic in both directions, you need two IPsec SAs: one for Router A → Router B (outbound from A's perspective) and one for Router B → Router A (inbound to A). This is why show crypto ipsec sa always shows two sets of SAs per peer.

7. What is the purpose of Diffie-Hellman in IKE Phase 1?

Correct answer is D. Diffie-Hellman is a public-key algorithm that solves the key distribution problem. Each peer generates a DH public/private key pair, exchanges only the public keys, and independently computes the same shared secret. This shared secret is never transmitted — an eavesdropper seeing both public keys cannot compute the shared secret without solving the discrete logarithm problem. The shared secret is then used to derive symmetric session keys for the Phase 1 SA.

8. What does the Cisco IOS command show crypto isakmp sa display, and what state indicates a healthy Phase 1 SA?

Correct answer is A. show crypto isakmp sa displays all Phase 1 ISAKMP Security Associations. The state QM_IDLE (Quick Mode Idle) means Phase 1 is fully established and ready — the peers have authenticated and have an active ISAKMP SA. From this state, Phase 2 (Quick Mode) negotiations can proceed. A state of MM_NO_STATE or deletion indicates Phase 1 failed.

9. What is Perfect Forward Secrecy (PFS) in IPsec, and why is it used?

Correct answer is C. Without PFS, Phase 2 SAs derive their keys from the same DH shared secret established in Phase 1. If an attacker eventually obtains the Phase 1 key material, they could potentially decrypt all past and future Phase 2 sessions derived from it. PFS breaks this dependency by performing a fresh Diffie-Hellman exchange for every Phase 2 renegotiation, ensuring each session's keys are independent of all others.

10. An IPsec VPN tunnel is established, but no data traffic is being encrypted. show crypto isakmp sa shows QM_IDLE (Phase 1 up), but show crypto ipsec sa shows zero encaps/decaps. What is the most likely cause?

Correct answer is B. When Phase 1 is up (QM_IDLE) but no packets are being encrypted (zero encaps in show crypto ipsec sa), the most common cause is a misconfigured crypto ACL. The ACL defines "interesting traffic" — the traffic that should trigger IPsec encryption. If the source/destination subnets in the ACL on either end do not exactly match (they must be mirror images of each other), no traffic will match the ACL and Phase 2 will never be triggered. Verify with show crypto map and check that the ACL entries correctly reflect the local and remote subnets.

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