Key management attacks¶
Attack pattern¶
Before IPsec protects anything, IKE has to agree the keys and prove who each peer is, and that setup is the softest part. A pre-shared key chosen by a human and reused for years; IKEv1’s aggressive mode, which leaks enough to crack that key offline; a certificate authority that, once compromised, vouches for the attacker: break the key exchange and the tunnel it protects is open from the first packet.
1. Key management attacks [OR]
1.1 IKEv1/IKEv2 key negotiation flaws [OR]
1.1.1 IKEv1 Aggressive Mode weaknesses [OR]
1.1.1.1 PSK exposure to offline attacks
1.1.1.1.1 Capture of AM handshake for dictionary attack
1.1.1.1.2 Identity (IDi) leakage aids selection of candidate PSKs
1.1.1.1.3 Low-entropy PSKs enable rapid guessing
1.1.1.2 Authentication bypass via legacy IKEv1 modes (rare edge cases)
1.1.2 IKE state exhaustion / DoS [OR]
1.1.2.1 Flood of half-open IKE_SA_INIT exchanges
1.1.2.2 Retransmit amplification exploiting UDP-based IKE
1.1.2.3 Mis-implemented cookies or puzzles abused for DoS
1.1.3 Message/replay handling flaws [OR]
1.1.3.1 Replay of IKEv2 Message IDs (including ID 0 in HA setups)
1.1.3.2 Out-of-order or duplicate messages triggering SA inconsistencies
1.1.4 Cryptographic / oracle-style negotiation flaws [OR]
1.1.4.1 Bleichenbacher-style oracles in RSA-based IKEv1
1.1.4.2 Distinct error/notify messages revealing validation state
1.1.5 INITIAL_CONTACT and delete notifies [AND]
1.1.5.1 Spoofing or injection requires bypassing cryptographic binding
1.1.5.2 Potential for unauthenticated traffic to trigger SA changes if misused
1.2 Pre-shared key brute-force attacks [OR]
1.2.1 Offline PSK cracking from captured handshakes [OR]
1.2.1.1 IKEv1 Aggressive Mode handshake capture
1.2.1.2 Weak PSKs susceptible to GPU/cluster attacks
1.2.2 Active-attacker oracles against PSK flows [OR]
1.2.2.1 IKEv2 misconfiguration or legacy modes leak accept/reject
1.2.2.2 Timing or response differences reveal PSK guesses
1.2.3 Poor key derivation assumptions [OR]
1.2.3.1 PRFs are not slow KDFs; entropy counts more than iteration
1.2.3.2 Predictable or human-generated PSKs reduce effective strength
1.2.4 Side-channel / implementation bugs [OR]
1.2.4.1 Non-constant-time comparisons leak information
1.2.4.2 Verbose notify messages reveal validation outcomes
1.3 Certificate authority and trust-store compromise [OR]
1.3.1 Rogue or compromised CA [OR]
1.3.1.1 Issuance of fraudulent certificates
1.3.1.2 Trusted certificate chain compromise
1.3.2 Trust anchor manipulation on endpoints [OR]
1.3.2.1 Malicious root or intermediate insertion
1.3.2.2 Enterprise policy bypass / endpoint compromise
1.3.3 Revocation weaknesses [OR]
1.3.3.1 OCSP responder spoofing or unavailability
1.3.3.2 CRL distribution tampering or unreachability
1.3.4 Intermediate CA key compromise [OR]
1.3.4.1 Valid-looking certificates issued until detection
1.3.4.2 Ecosystem-wide impact until revocation
1.4 Key lifetimes, rekeying, and time-source attacks [OR]
1.4.1 SA lifetime misconfigurations [OR]
1.4.1.1 Excessive lifetime → reduced forward secrecy
1.4.1.2 Unsynchronised rekeying across peers
1.4.2 Forged or skewed time affecting validation [OR]
1.4.2.1 NTP time-shifting attacks impacting cert validation
1.4.2.2 Log timestamp inconsistencies enabling replay or audit gaps
1.4.3 Certificate validity window abuse [OR]
1.4.3.1 Exploiting acceptance of out-of-window certificates
1.4.3.2 Manipulating minor skew to bypass temporal checks
1.4.4 Audit and logging attacks [OR]
1.4.4.1 Unsynchronised clocks undermining non-repudiation
1.4.4.2 Tampering or deletion of logs affecting incident reconstruction
Broken at the handshake¶
IKEv1 Aggressive Mode enables offline PSK cracking; widely documented and formally analysed.
Libreswan IKEv1 retransmit amplification DoS (CVE-2016-5361, disputed by the project) and IKE cookie/puzzle DoS mitigation guidance.
IKEv2 Message ID replay considerations for HA sync (Message ID 0) in RFC 6311.
Bleichenbacher-style oracles and auth bypass in IKE (academic).
INITIAL_CONTACTis a cryptographically protected notify; pairing it with liveness checks reduces the exposure window.SA lifetimes are local policy in IKEv2, though IKEv1 negotiates them as SA attributes; typical hours and rekey behaviour.
Time shifting via NTP attacks can affect certificate validation/logging; RFC 5280 defines validity semantics; industry BRs cap certificate lifetimes.
Rogue CA/trust-store manipulation and real-world CA compromises.