Last week I updated to current. After the update, I was unable to establish an ikev2 VPN with any iOS devices. A OBSD6.1<->OBSD6.1 ikev2 VPN continued to work. All tunnels use certificates, and nothing was changed in the configuration/certificates during the system update. Prior to this update, iked had been working with iOS for at least 6 months.
Thanks to some detailed direction, it appears that iked fails after CVS patchset 394, dated 2017/03/23. Anyway, prior to the update, I had no issues. A connection from iOS to iked worked fine. To regress to prior version, I did: cd /usr/src TZ=UTC cvs up -D '2017/03/23 05:29:48' -P sbin/iked usr.sbin/ikectlcd sbin/iked make obj && make && sudo make install cd ../../usr.sbin/ikectl make obj && make && sudo make install Then started iked: (I have obfuscated the output a little) iked -dvv (...after loading configuration...) /etc/iked.conf: loaded 7 configuration rules ca_privkey_serialize: type RSA_KEY length 2349 ca_pubkey_serialize: type RSA_KEY length 526 config_getpolicy: received policy ca_getkey: received private key type RSA_KEY length 2349 ca_getkey: received public key type RSA_KEY length 526 ca_dispatch_parent: config reset config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpfkey: received pfkey fd 3 config_getcompile: compilation done config_getsocket: received socket fd 4 config_getsocket: received socket fd 5 config_getsocket: received socket fd 6 config_getsocket: received socket fd 7 ca_reload: loaded ca file ca.crt ca_reload: /C=US/ST=Illinois/... ca_reload: loaded 1 ca certificate ca_reload: loaded cert file ipsec1.myfqdn.com.crt ca_reload: loaded cert file ikesync.myfqdn.com.crt ca_validate_cert: /C=US/ST=Illinois/... ok ca_validate_cert: /C=US/ST=Illinois/... ok ca_reload: local cert type X509_CERT config_getocsp: ocsp_url none ikev2_dispatch_cert: updated local CERTREQ type X509_CERT length 20 ikev2_dispatch_cert: updated local CERTREQ type X509_CERT length 20 ikev2_recv: IKE_SA_INIT request from initiator xxx.yyy.1.254:61856 to xxx.yyy.1.20:500 policy 'ios1_vpn' id 0, 432 bytes ikev2_recv: ispi 0x08167d0d9b45d2a1 rspi 0x0000000000000000 ikev2_policy2id: srcid FQDN/ikesync.myfqdn.com length 27 ikev2_pld_parse: header ispi 0x08167d0d9b45d2a1 rspi 0x0000000000000000 nextpayload SA version 0x20 exchange IKE_SA_INIT flags 0x08 msgid 0 length 432 response 0 ikev2_pld_payloads: payload SA nextpayload KE critical 0x00 length 48 ikev2_pld_sa: more 0 reserved 0 length 44 proposal #1 protoid IKE spisize 0 xforms 4 spi 0 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type PRF id HMAC_SHA2_256 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type DH id MODP_2048 ikev2_pld_payloads: payload KE nextpayload NONCE critical 0x00 length 264 ikev2_pld_ke: dh group MODP_2048 reserved 0 ikev2_pld_payloads: payload NONCE nextpayload NOTIFY critical 0x00 length 20 ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type REDIRECT_SUPPORTED ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_SOURCE_IP ikev2_nat_detection: peer source 0x08167d0d9b45d2a1 0x0000000000000000 xxx.yyy.1.254:61856 ikev2_pld_notify: NAT_DETECTION_SOURCE_IP detected NAT, enabling UDP encapsulation ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_DESTINATION_IP ikev2_nat_detection: peer destination 0x08167d0d9b45d2a1 0x0000000000000000 xxx.yyy.1.20:500 ikev2_pld_payloads: payload NOTIFY nextpayload NONE critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type FRAGMENTATION_SUPPORTED sa_state: INIT -> SA_INIT ikev2_sa_negotiate: score 4 sa_stateok: SA_INIT flags 0x0000, require 0x0000 sa_stateflags: 0x0000 -> 0x0020 sa (required 0x0000 ) ikev2_sa_keys: SKEYSEED with 32 bytes ikev2_sa_keys: S with 64 bytes ikev2_prfplus: T1 with 32 bytes ikev2_prfplus: T2 with 32 bytes ikev2_prfplus: T3 with 32 bytes ikev2_prfplus: T4 with 32 bytes ikev2_prfplus: T5 with 32 bytes ikev2_prfplus: T6 with 32 bytes ikev2_prfplus: T7 with 32 bytes ikev2_prfplus: Tn with 224 bytes ikev2_sa_keys: SK_d with 32 bytes ikev2_sa_keys: SK_ai with 32 bytes ikev2_sa_keys: SK_ar with 32 bytes ikev2_sa_keys: SK_ei with 32 bytes ikev2_sa_keys: SK_er with 32 bytes ikev2_sa_keys: SK_pi with 32 bytes ikev2_sa_keys: SK_pr with 32 bytes ikev2_add_proposals: length 44 ikev2_next_payload: length 48 nextpayload KE ikev2_next_payload: length 264 nextpayload NONCE ikev2_next_payload: length 36 nextpayload NOTIFY ikev2_nat_detection: local source 0x08167d0d9b45d2a1 0x4c664ee08c8afe58 xxx.yyy.1.20:500 ikev2_next_payload: length 28 nextpayload NOTIFY ikev2_nat_detection: local destination 0x08167d0d9b45d2a1 0x4c664ee08c8afe58 xxx.yyy.1.254:61856 ikev2_next_payload: length 28 nextpayload CERTREQ ikev2_add_certreq: type X509_CERT length 21 ikev2_next_payload: length 25 nextpayload NONE ikev2_pld_parse: header ispi 0x08167d0d9b45d2a1 rspi 0x4c664ee08c8afe58 nextpayload SA version 0x20 exchange IKE_SA_INIT flags 0x20 msgid 0 length 457 response 1 ikev2_pld_payloads: payload SA nextpayload KE critical 0x00 length 48 ikev2_pld_sa: more 0 reserved 0 length 44 proposal #1 protoid IKE spisize 0 xforms 4 spi 0 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type PRF id HMAC_SHA2_256 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type DH id MODP_2048 ikev2_pld_payloads: payload KE nextpayload NONCE critical 0x00 length 264 ikev2_pld_ke: dh group MODP_2048 reserved 0 ikev2_pld_payloads: payload NONCE nextpayload NOTIFY critical 0x00 length 36 ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_SOURCE_IP ikev2_pld_payloads: payload NOTIFY nextpayload CERTREQ critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_DESTINATION_IP ikev2_pld_payloads: payload CERTREQ nextpayload NONE critical 0x00 length 25 ikev2_pld_certreq: type X509_CERT length 20 ikev2_msg_send: IKE_SA_INIT response from xxx.yyy.1.20:500 to xxx.yyy.1.254:61856 msgid 0, 457 bytes config_free_proposals: free 0x1b1485a1c380 ikev2_recv: IKE_AUTH request from initiator xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios1_vpn' id 1, 2928 bytes ikev2_recv: ispi 0x08167d0d9b45d2a1 rspi 0x4c664ee08c8afe58 ikev2_recv: updated SA to peer xxx.yyy.1.254:62164 local xxx.yyy.1.20:4500 ikev2_pld_parse: header ispi 0x08167d0d9b45d2a1 rspi 0x4c664ee08c8afe58 nextpayload SK version 0x20 exchange IKE_AUTH flags 0x08 msgid 1 length 2928 response 0 ikev2_pld_payloads: payload SK nextpayload IDi critical 0x00 length 2900 ikev2_msg_decrypt: IV length 16 ikev2_msg_decrypt: encrypted payload length 2864 ikev2_msg_decrypt: integrity checksum length 16 ikev2_msg_decrypt: integrity check succeeded ikev2_msg_decrypt: decrypted payload length 2864/2864 padding 14 ikev2_pld_payloads: decrypted payload IDi nextpayload NOTIFY critical 0x00 length 40 ikev2_pld_id: id FQDN/ios2.ikev2.myfqdn.com length 36 ikev2_pld_payloads: decrypted payload NOTIFY nextpayload IDr critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type INITIAL_CONTACT ikev2_pld_payloads: decrypted payload IDr nextpayload AUTH critical 0x00 length 31 ikev2_pld_id: id FQDN/ikesync.myfqdn.com length 27 ikev2_pld_id: unexpected id payload ikev2_pld_payloads: decrypted payload AUTH nextpayload CERT critical 0x00 length 520 ikev2_pld_auth: method RSA_SIG length 512 sa_state: SA_INIT -> AUTH_REQUEST ikev2_pld_payloads: decrypted payload CERT nextpayload CP critical 0x00 length 1997 ikev2_pld_cert: type X509_CERT length 1992 ikev2_pld_payloads: decrypted payload CP nextpayload NOTIFY critical 0x00 length 65 ikev2_pld_cp: type REQUEST length 57 ikev2_pld_cp: INTERNAL_IP4_ADDRESS 0x0001 length 0 ikev2_pld_cp: INTERNAL_IP4_SUBNET 0x000d length 0 ikev2_pld_cp: INTERNAL_IP4_DHCP 0x0006 length 0 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 0 ikev2_pld_cp: INTERNAL_IP4_NETMASK 0x0002 length 0 ikev2_pld_cp: INTERNAL_IP6_ADDRESS 0x0008 length 0 ikev2_pld_cp: INTERNAL_IP6_SUBNET 0x000f length 17 ikev2_pld_cp: INTERNAL_IP6_DHCP 0x000c length 0 ikev2_pld_cp: INTERNAL_IP6_DNS 0x000a length 0 ikev2_pld_cp: <UNKNOWN:25> 0x0019 length 0 ikev2_pld_payloads: decrypted payload NOTIFY nextpayload NOTIFY critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type ESP_TFC_PADDING_NOT_SUPPORTED ikev2_pld_payloads: decrypted payload NOTIFY nextpayload SA critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type NON_FIRST_FRAGMENTS_ALSO ikev2_pld_payloads: decrypted payload SA nextpayload TSi critical 0x00 length 44 ikev2_pld_sa: more 0 reserved 0 length 40 proposal #1 protoid ESP spisize 4 xforms 3 spi 0x08faa176 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type ESN id NONE ikev2_pld_payloads: decrypted payload TSi nextpayload TSr critical 0x00 length 64 ikev2_pld_ts: count 2 length 56 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_pld_ts: type IPV6_ADDR_RANGE protoid 0 length 40 startport 0 endport 65535 ikev2_pld_ts: start :: end ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff ikev2_pld_payloads: decrypted payload TSr nextpayload NONE critical 0x00 length 64 ikev2_pld_ts: count 2 length 56 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_pld_ts: type IPV6_ADDR_RANGE protoid 0 length 40 startport 0 endport 65535 ikev2_pld_ts: start :: end ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff ikev2_resp_recv: NAT-T message received, updated SA sa_stateok: SA_INIT flags 0x0000, require 0x0000 policy_lookup: peerid 'ios2.ikev2.myfqdn.com' ikev2_msg_auth: responder auth data length 505 ca_setauth: auth length 505 ikev2_msg_auth: initiator auth data length 496 ikev2_msg_authverify: method RSA_SIG keylen 1992 type X509_CERT ikev2_msg_authverify: authentication successful sa_state: AUTH_REQUEST -> AUTH_SUCCESS sa_stateflags: 0x0020 -> 0x0030 authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) ikev2_sa_negotiate: score 4 sa_stateflags: 0x0030 -> 0x0030 authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x0030, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: cannot switch: AUTH_SUCCESS -> VALID ikev2_ike_auth: no CERTREQ, using default ikev2_policy2id: srcid FQDN/ikesync.myfqdn.com length 27 sa_stateflags: 0x0030 -> 0x0034 certreq,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) config_free_proposals: free 0x1b1485a1ca80 ca_setauth: auth length 512 ca_x509_subjectaltname: FQDN/ios2.ikev2.myfqdn.com ca_validate_cert: /C=US/ST=Illinois/... ok ca_getreq: found CA /C=US/ST=Illinois/... ikev2_getimsgdata: imsg 23 rspi 0x4c664ee08c8afe58 ispi 0x08167d0d9b45d2a1 initiator 0 sa valid type 1 data length 512 ikev2_dispatch_cert: AUTH type 1 len 512 sa_stateflags: 0x0034 -> 0x003c certreq,auth,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x0038, require 0x003b cert,certvalid,auth,authvalid,sa ca_x509_subjectaltname: FQDN/ipsec1.myfqdn.com sa_state: cannot switch: AUTH_SUCCESS -> VALID ca_x509_subjectaltname_cmp: FQDN/ipsec1.myfqdn.com mismatched ikev2_dispatch_cert: peer certificate is valid sa_stateflags: 0x003c -> 0x003e certvalid,certreq,auth,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) ca_x509_subjectaltname: FQDN/ikesync.myfqdn.com sa_stateok: VALID flags 0x003a, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: cannot switch: AUTH_SUCCESS -> VALID ca_getreq: found local certificate /C=US/ST=Illinois/... ikev2_getimsgdata: imsg 18 rspi 0x4c664ee08c8afe58 ispi 0x08167d0d9b45d2a1 initiator 0 sa valid type 4 data length 1976 ikev2_dispatch_cert: cert type X509_CERT length 1976, ok sa_stateflags: 0x003e -> 0x003f cert,certvalid,certreq,auth,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x003b, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: AUTH_SUCCESS -> VALID sa_stateok: VALID flags 0x003b, require 0x003b cert,certvalid,auth,authvalid,sa sa_stateok: VALID flags 0x003b, require 0x003b cert,certvalid,auth,authvalid,sa ikev2_sa_tag: (0) ikev2_childsa_negotiate: proposal 1 ikev2_childsa_negotiate: key material length 128 ikev2_prfplus: T1 with 32 bytes ikev2_prfplus: T2 with 32 bytes ikev2_prfplus: T3 with 32 bytes ikev2_prfplus: T4 with 32 bytes ikev2_prfplus: Tn with 128 bytes pfkey_sa_getspi: spi 0x7d9d47d1 pfkey_sa_init: new spi 0x7d9d47d1 ikev2_next_payload: length 31 nextpayload CERT ikev2_next_payload: length 1981 nextpayload AUTH ikev2_next_payload: length 520 nextpayload CP ikev2_next_payload: length 48 nextpayload SA ikev2_add_proposals: length 40 ikev2_next_payload: length 44 nextpayload TSi ikev2_next_payload: length 24 nextpayload TSr ikev2_next_payload: length 24 nextpayload NONE ikev2_msg_encrypt: decrypted length 2672 ikev2_msg_encrypt: padded length 2688 ikev2_msg_encrypt: length 2673, padding 15, output length 2720 ikev2_next_payload: length 2724 nextpayload IDr ikev2_msg_integr: message length 2752 ikev2_msg_integr: integrity checksum length 16 ikev2_pld_parse: header ispi 0x08167d0d9b45d2a1 rspi 0x4c664ee08c8afe58 nextpayload SK version 0x20 exchange IKE_AUTH flags 0x20 msgid 1 length 2752 response 1 ikev2_pld_payloads: payload SK nextpayload IDr critical 0x00 length 2724 ikev2_msg_decrypt: IV length 16 ikev2_msg_decrypt: encrypted payload length 2688 ikev2_msg_decrypt: integrity checksum length 16 ikev2_msg_decrypt: integrity check succeeded ikev2_msg_decrypt: decrypted payload length 2688/2688 padding 15 ikev2_pld_payloads: decrypted payload IDr nextpayload CERT critical 0x00 length 31 ikev2_pld_id: id FQDN/ikesync.myfqdn.com length 27 ikev2_pld_payloads: decrypted payload CERT nextpayload AUTH critical 0x00 length 1981 ikev2_pld_cert: type X509_CERT length 1976 ikev2_pld_payloads: decrypted payload AUTH nextpayload CP critical 0x00 length 520 ikev2_pld_auth: method RSA_SIG length 512 ikev2_pld_payloads: decrypted payload CP nextpayload SA critical 0x00 length 48 ikev2_pld_cp: type REPLY length 40 ikev2_pld_cp: INTERNAL_IP4_ADDRESS 0x0001 length 4 ikev2_pld_cp: INTERNAL_IP4_NETMASK 0x0002 length 4 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 4 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 4 ikev2_pld_cp: INTERNAL_IP4_NBNS 0x0004 length 4 ikev2_pld_payloads: decrypted payload SA nextpayload TSi critical 0x00 length 44 ikev2_pld_sa: more 0 reserved 0 length 40 proposal #1 protoid ESP spisize 4 xforms 3 spi 0x7d9d47d1 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type ESN id NONE ikev2_pld_payloads: decrypted payload TSi nextpayload TSr critical 0x00 length 24 ikev2_pld_ts: count 1 length 16 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start xxx.yyy.15.0 end xxx.yyy.15.255 ikev2_pld_payloads: decrypted payload TSr nextpayload NONE critical 0x00 length 24 ikev2_pld_ts: count 1 length 16 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_msg_send: IKE_AUTH response from xxx.yyy.1.20:4500 to xxx.yyy.1.254:62164 msgid 1, 2752 bytes, NAT-T pfkey_sa_add: update spi 0x7d9d47d1 pfkey_sa: udpencap port 62164 ikev2_childsa_enable: loaded CHILD SA spi 0x7d9d47d1 pfkey_sa_add: add spi 0x08faa176 pfkey_sa: udpencap port 62164 ikev2_childsa_enable: loaded CHILD SA spi 0x08faa176 ikev2_childsa_enable: loaded flow 0x1b143bce6c00 ikev2_childsa_enable: loaded flow 0x1b142e8f8c00 sa_state: VALID -> ESTABLISHED from xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios2_vpn' ^Cikev2 exiting, pid 68371 ca exiting, pid 65397 control exiting, pid 51297 parent terminating But, when I compile from the next patchset - same procedure as above except: TZ=UTC cvs up -D '2017/03/27 11:06:41' -P sbin/iked usr.sbin/ikectl Now, when I try to connect with iOS, the VPN fails. iked -dvv (...after loading configuration...) /etc/iked.conf: loaded 7 configuration rules ca_privkey_serialize: type RSA_KEY length 2349 ca_pubkey_serialize: type RSA_KEY length 526 config_getpolicy: received policy ca_privkey_to_method: type RSA_KEY method RSA_SIG ca_getkey: received private key type RSA_KEY length 2349 ca_getkey: received public key type RSA_KEY length 526 ca_dispatch_parent: config reset config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpfkey: received pfkey fd 3 config_getcompile: compilation done config_getsocket: received socket fd 4 config_getsocket: received socket fd 5 config_getsocket: received socket fd 6 config_getsocket: received socket fd 7 ca_reload: loaded ca file ca.crt ca_reload: /C=US/ST=Illinois/... ca_reload: loaded 1 ca certificate ca_reload: loaded cert file ipsec1.myfqdn.com.crt ca_reload: loaded cert file ikesync.myfqdn.com.crt ca_validate_cert: /C=US/ST=Illinois/... ok ca_validate_cert: /C=US/ST=Illinois/... ok ca_reload: local cert type X509_CERT config_getocsp: ocsp_url none ikev2_dispatch_cert: updated local CERTREQ type X509_CERT length 20 ikev2_dispatch_cert: updated local CERTREQ type X509_CERT length 20 ikev2_recv: IKE_SA_INIT request from initiator xxx.yyy.1.254:57991 to xxx.yyy.1.20:500 policy 'ios1_vpn' id 0, 432 bytes ikev2_recv: ispi 0x36d074d6d42e05d3 rspi 0x0000000000000000 ikev2_policy2id: srcid FQDN/ikesync.myfqdn.com length 27 ikev2_pld_parse: header ispi 0x36d074d6d42e05d3 rspi 0x0000000000000000 nextpayload SA version 0x20 exchange IKE_SA_INIT flags 0x08 msgid 0 length 432 response 0 ikev2_pld_payloads: payload SA nextpayload KE critical 0x00 length 48 ikev2_pld_sa: more 0 reserved 0 length 44 proposal #1 protoid IKE spisize 0 xforms 4 spi 0 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type PRF id HMAC_SHA2_256 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type DH id MODP_2048 ikev2_pld_payloads: payload KE nextpayload NONCE critical 0x00 length 264 ikev2_pld_ke: dh group MODP_2048 reserved 0 ikev2_pld_payloads: payload NONCE nextpayload NOTIFY critical 0x00 length 20 ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type REDIRECT_SUPPORTED ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_SOURCE_IP ikev2_nat_detection: peer source 0x36d074d6d42e05d3 0x0000000000000000 xxx.yyy.1.254:57991 ikev2_pld_notify: NAT_DETECTION_SOURCE_IP detected NAT, enabling UDP encapsulation ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_DESTINATION_IP ikev2_nat_detection: peer destination 0x36d074d6d42e05d3 0x0000000000000000 xxx.yyy.1.20:500 ikev2_pld_payloads: payload NOTIFY nextpayload NONE critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type FRAGMENTATION_SUPPORTED sa_state: INIT -> SA_INIT ikev2_sa_negotiate: score 4 sa_stateok: SA_INIT flags 0x0000, require 0x0000 sa_stateflags: 0x0000 -> 0x0020 sa (required 0x0000 ) ikev2_sa_keys: SKEYSEED with 32 bytes ikev2_sa_keys: S with 64 bytes ikev2_prfplus: T1 with 32 bytes ikev2_prfplus: T2 with 32 bytes ikev2_prfplus: T3 with 32 bytes ikev2_prfplus: T4 with 32 bytes ikev2_prfplus: T5 with 32 bytes ikev2_prfplus: T6 with 32 bytes ikev2_prfplus: T7 with 32 bytes ikev2_prfplus: Tn with 224 bytes ikev2_sa_keys: SK_d with 32 bytes ikev2_sa_keys: SK_ai with 32 bytes ikev2_sa_keys: SK_ar with 32 bytes ikev2_sa_keys: SK_ei with 32 bytes ikev2_sa_keys: SK_er with 32 bytes ikev2_sa_keys: SK_pi with 32 bytes ikev2_sa_keys: SK_pr with 32 bytes ikev2_add_proposals: length 44 ikev2_next_payload: length 48 nextpayload KE ikev2_next_payload: length 264 nextpayload NONCE ikev2_next_payload: length 36 nextpayload NOTIFY ikev2_nat_detection: local source 0x36d074d6d42e05d3 0x1b014b76b97d2731 xxx.yyy.1.20:500 ikev2_next_payload: length 28 nextpayload NOTIFY ikev2_nat_detection: local destination 0x36d074d6d42e05d3 0x1b014b76b97d2731 xxx.yyy.1.254:57991 ikev2_next_payload: length 28 nextpayload CERTREQ ikev2_add_certreq: type X509_CERT length 21 ikev2_next_payload: length 25 nextpayload NONE ikev2_pld_parse: header ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 nextpayload SA version 0x20 exchange IKE_SA_INIT flags 0x20 msgid 0 length 457 response 1 ikev2_pld_payloads: payload SA nextpayload KE critical 0x00 length 48 ikev2_pld_sa: more 0 reserved 0 length 44 proposal #1 protoid IKE spisize 0 xforms 4 spi 0 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type PRF id HMAC_SHA2_256 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type DH id MODP_2048 ikev2_pld_payloads: payload KE nextpayload NONCE critical 0x00 length 264 ikev2_pld_ke: dh group MODP_2048 reserved 0 ikev2_pld_payloads: payload NONCE nextpayload NOTIFY critical 0x00 length 36 ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_SOURCE_IP ikev2_pld_payloads: payload NOTIFY nextpayload CERTREQ critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_DESTINATION_IP ikev2_pld_payloads: payload CERTREQ nextpayload NONE critical 0x00 length 25 ikev2_pld_certreq: type X509_CERT length 20 ikev2_msg_send: IKE_SA_INIT response from xxx.yyy.1.20:500 to xxx.yyy.1.254:57991 msgid 0, 457 bytes config_free_proposals: free 0xc5bdb73c680 ikev2_recv: IKE_AUTH request from initiator xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios1_vpn' id 1, 2928 bytes ikev2_recv: ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 ikev2_recv: updated SA to peer xxx.yyy.1.254:62164 local xxx.yyy.1.20:4500 ikev2_pld_parse: header ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 nextpayload SK version 0x20 exchange IKE_AUTH flags 0x08 msgid 1 length 2928 response 0 ikev2_pld_payloads: payload SK nextpayload IDi critical 0x00 length 2900 ikev2_msg_decrypt: IV length 16 ikev2_msg_decrypt: encrypted payload length 2864 ikev2_msg_decrypt: integrity checksum length 16 ikev2_msg_decrypt: integrity check succeeded ikev2_msg_decrypt: decrypted payload length 2864/2864 padding 14 ikev2_pld_payloads: decrypted payload IDi nextpayload NOTIFY critical 0x00 length 40 ikev2_pld_id: id FQDN/ios2.ikev2.myfqdn.com length 36 ikev2_pld_payloads: decrypted payload NOTIFY nextpayload IDr critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type INITIAL_CONTACT ikev2_pld_payloads: decrypted payload IDr nextpayload AUTH critical 0x00 length 31 ikev2_pld_id: id FQDN/ikesync.myfqdn.com length 27 ikev2_pld_id: unexpected id payload ikev2_pld_payloads: decrypted payload AUTH nextpayload CERT critical 0x00 length 520 ikev2_pld_auth: method RSA_SIG length 512 sa_state: SA_INIT -> AUTH_REQUEST ikev2_pld_payloads: decrypted payload CERT nextpayload CP critical 0x00 length 1997 ikev2_pld_cert: type X509_CERT length 1992 ikev2_pld_payloads: decrypted payload CP nextpayload NOTIFY critical 0x00 length 65 ikev2_pld_cp: type REQUEST length 57 ikev2_pld_cp: INTERNAL_IP4_ADDRESS 0x0001 length 0 ikev2_pld_cp: INTERNAL_IP4_SUBNET 0x000d length 0 ikev2_pld_cp: INTERNAL_IP4_DHCP 0x0006 length 0 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 0 ikev2_pld_cp: INTERNAL_IP4_NETMASK 0x0002 length 0 ikev2_pld_cp: INTERNAL_IP6_ADDRESS 0x0008 length 0 ikev2_pld_cp: INTERNAL_IP6_SUBNET 0x000f length 17 ikev2_pld_cp: INTERNAL_IP6_DHCP 0x000c length 0 ikev2_pld_cp: INTERNAL_IP6_DNS 0x000a length 0 ikev2_pld_cp: <UNKNOWN:25> 0x0019 length 0 ikev2_pld_payloads: decrypted payload NOTIFY nextpayload NOTIFY critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type ESP_TFC_PADDING_NOT_SUPPORTED ikev2_pld_payloads: decrypted payload NOTIFY nextpayload SA critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type NON_FIRST_FRAGMENTS_ALSO ikev2_pld_payloads: decrypted payload SA nextpayload TSi critical 0x00 length 44 ikev2_pld_sa: more 0 reserved 0 length 40 proposal #1 protoid ESP spisize 4 xforms 3 spi 0x0a7c828c ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type ESN id NONE ikev2_pld_payloads: decrypted payload TSi nextpayload TSr critical 0x00 length 64 ikev2_pld_ts: count 2 length 56 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_pld_ts: type IPV6_ADDR_RANGE protoid 0 length 40 startport 0 endport 65535 ikev2_pld_ts: start :: end ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff ikev2_pld_payloads: decrypted payload TSr nextpayload NONE critical 0x00 length 64 ikev2_pld_ts: count 2 length 56 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_pld_ts: type IPV6_ADDR_RANGE protoid 0 length 40 startport 0 endport 65535 ikev2_pld_ts: start :: end ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff ikev2_resp_recv: NAT-T message received, updated SA sa_stateok: SA_INIT flags 0x0000, require 0x0000 policy_lookup: peerid 'ios2.ikev2.myfqdn.com' ikev2_msg_auth: responder auth data length 505 ca_setauth: using SIG (RFC7427) ca_setauth: auth length 505 ikev2_ike_auth_recv: unexpected auth method RSA_SIG, was expecting SIG ikev2_resp_recv: failed to send auth response sa_state: AUTH_REQUEST -> CLOSED from xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios2_vpn' ikev2_recv: closing SA sa_free: ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 config_free_proposals: free 0xc5bdb73c380 config_free_proposals: free 0xc5bdb73c000 ca_setauth: auth length 528 ca_x509_subjectaltname: FQDN/ios2.ikev2.myfqdn.com ca_validate_cert: /C=US/ST=Illinois/... ok ikev2_getimsgdata: imsg 24 rspi 0x1b014b76b97d2731 ispi 0x36d074d6d42e05d3 initiator 0 sa invalid type 14 data length 528 ikev2_dispatch_cert: invalid auth reply ikev2_recv: IKE_AUTH request from initiator xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios1_vpn' id 1, 2928 bytes ikev2_recv: ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 ikev2_recv: IKE_AUTH request from initiator xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios1_vpn' id 1, 2928 bytes ikev2_recv: ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 ikev2_recv: IKE_AUTH request from initiator xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios1_vpn' id 1, 2928 bytes ikev2_recv: ispi 0x36d074d6d42e05d3 rspi 0x1b014b76b97d2731 ^Cikev2 exiting, pid 1899 ca exiting, pid 95316 control exiting, pid 71888 parent terminating In this case, there is an error, and the tunnel is CLOSED. ikev2_ike_auth_recv: unexpected auth method RSA_SIG, was expecting SIG ikev2_resp_recv: failed to send auth response sa_state: AUTH_REQUEST -> CLOSED from xxx.yyy.1.254:62164 to xxx.yyy.1.20:4500 policy 'ios2_vpn' Before learning how to go back in time, I found a suggestion that placing an RSA public certificate on the local OBSD machine could help. So, I used: # openssl rsa -in private.key -pubout > /etc/iked/pubkeys/fqdn/ios.ikev2.myfqdn.com When this is done with the newer updates (the ones that fail to create a VPN with iOS), then the OBSD machine indicates that a tunnel has been formed, but the iOS device fails to create the tunnel, and indicates that no VPN has been established. set_policy_auth_method: using rsa for peer /etc/iked/pubkeys/fqdn/ios.ikev2.myfqdn.com set_policy: found pubkey for /etc/iked/pubkeys/fqdn/ios.ikev2.myfqdn.com ikev2 "ios_vpn" passive esp inet from 0.0.0.0/0 to xxx.yyy.15.0/24 local xxx.yyy.1.20 peer any ikesa enc aes-256,aes-192,aes-128,3des prf hmac-sha2-256,hmac-sha1 auth hmac-sha2-256,hmac-sha1 group modp2048,modp1536,modp1024 childsa enc aes-256,aes-192,aes-128 auth hmac-sha2-256,hmac-sha1 srcid ikesync.myfqdn.com dstid ios.ikev2.myfqdn.com ikelifetime 1800 lifetime 1800 bytes 536870912 rsa config address xxx.yyy.15.131 config netmask 255.255.255.0 config name-server xxx.yyy.1.128 config name-server xxx.yyy.1.129 config netbios-server xxx.yyy.2.99 ca_privkey_serialize: type RSA_KEY length 2349 ca_pubkey_serialize: type RSA_KEY length 526 ca_privkey_to_method: type RSA_KEY method RSA_SIG config_getpolicy: received policy ca_getkey: received private key type RSA_KEY length 2349 ca_getkey: received public key type RSA_KEY length 526 ca_dispatch_parent: config reset config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpolicy: received policy config_getpfkey: received pfkey fd 3 config_getcompile: compilation done config_getsocket: received socket fd 4 config_getsocket: received socket fd 5 config_getsocket: received socket fd 6 config_getsocket: received socket fd 7 ca_reload: loaded ca file ca.crt ca_reload: /C=US/ST=Illinois... ca_reload: loaded 1 ca certificate ca_reload: loaded cert file local.myfqdn.com.crt ca_reload: loaded cert file ikesync.myfqdn.com.crt ca_validate_cert: /C=US/ST=Illinois... ok ca_validate_cert: /C=US/ST=Illinois... ok ca_reload: local cert type X509_CERT config_getocsp: ocsp_url none ikev2_dispatch_cert: updated local CERTREQ type X509_CERT length 20 ikev2_dispatch_cert: updated local CERTREQ type X509_CERT length 20 ikev2_recv: IKE_SA_INIT request from initiator xxx.yyy.1.254:55008 to xxx.yyy.1.20:500 policy 'jacqueline_iphone_vpn' id 0, 432 bytes ikev2_recv: ispi 0xd14315b81593285a rspi 0x0000000000000000 ikev2_policy2id: srcid FQDN/ikesync.myfqdn.com length 27 ikev2_pld_parse: header ispi 0xd14315b81593285a rspi 0x0000000000000000 nextpayload SA version 0x20 exchange IKE_SA_INIT flags 0x08 msgid 0 length 432 response 0 ikev2_pld_payloads: payload SA nextpayload KE critical 0x00 length 48 ikev2_pld_sa: more 0 reserved 0 length 44 proposal #1 protoid IKE spisize 0 xforms 4 spi 0 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type PRF id HMAC_SHA2_256 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type DH id MODP_2048 ikev2_pld_payloads: payload KE nextpayload NONCE critical 0x00 length 264 ikev2_pld_ke: dh group MODP_2048 reserved 0 ikev2_pld_payloads: payload NONCE nextpayload NOTIFY critical 0x00 length 20 ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type REDIRECT_SUPPORTED ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_SOURCE_IP ikev2_nat_detection: peer source 0xd14315b81593285a 0x0000000000000000 xxx.yyy.1.254:55008 ikev2_pld_notify: NAT_DETECTION_SOURCE_IP detected NAT, enabling UDP encapsulation ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_DESTINATION_IP ikev2_nat_detection: peer destination 0xd14315b81593285a 0x0000000000000000 xxx.yyy.1.20:500 ikev2_pld_payloads: payload NOTIFY nextpayload NONE critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type FRAGMENTATION_SUPPORTED sa_state: INIT -> SA_INIT ikev2_sa_negotiate: score 4 sa_stateok: SA_INIT flags 0x0000, require 0x0000 sa_stateflags: 0x0000 -> 0x0020 sa (required 0x0000 ) ikev2_sa_keys: SKEYSEED with 32 bytes ikev2_sa_keys: S with 64 bytes ikev2_prfplus: T1 with 32 bytes ikev2_prfplus: T2 with 32 bytes ikev2_prfplus: T3 with 32 bytes ikev2_prfplus: T4 with 32 bytes ikev2_prfplus: T5 with 32 bytes ikev2_prfplus: T6 with 32 bytes ikev2_prfplus: T7 with 32 bytes ikev2_prfplus: Tn with 224 bytes ikev2_sa_keys: SK_d with 32 bytes ikev2_sa_keys: SK_ai with 32 bytes ikev2_sa_keys: SK_ar with 32 bytes ikev2_sa_keys: SK_ei with 32 bytes ikev2_sa_keys: SK_er with 32 bytes ikev2_sa_keys: SK_pi with 32 bytes ikev2_sa_keys: SK_pr with 32 bytes ikev2_add_proposals: length 44 ikev2_next_payload: length 48 nextpayload KE ikev2_next_payload: length 264 nextpayload NONCE ikev2_next_payload: length 36 nextpayload NOTIFY ikev2_nat_detection: local source 0xd14315b81593285a 0x9f30f9d2ed8dfd11 xxx.yyy.1.20:500 ikev2_next_payload: length 28 nextpayload NOTIFY ikev2_nat_detection: local destination 0xd14315b81593285a 0x9f30f9d2ed8dfd11 xxx.yyy.1.254:55008 ikev2_next_payload: length 28 nextpayload CERTREQ ikev2_add_certreq: type X509_CERT length 21 ikev2_next_payload: length 25 nextpayload CERTREQ ikev2_add_certreq: type RSA_KEY length 1 ikev2_next_payload: length 5 nextpayload NONE ikev2_pld_parse: header ispi 0xd14315b81593285a rspi 0x9f30f9d2ed8dfd11 nextpayload SA version 0x20 exchange IKE_SA_INIT flags 0x20 msgid 0 length 462 response 1 ikev2_pld_payloads: payload SA nextpayload KE critical 0x00 length 48 ikev2_pld_sa: more 0 reserved 0 length 44 proposal #1 protoid IKE spisize 0 xforms 4 spi 0 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type PRF id HMAC_SHA2_256 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type DH id MODP_2048 ikev2_pld_payloads: payload KE nextpayload NONCE critical 0x00 length 264 ikev2_pld_ke: dh group MODP_2048 reserved 0 ikev2_pld_payloads: payload NONCE nextpayload NOTIFY critical 0x00 length 36 ikev2_pld_payloads: payload NOTIFY nextpayload NOTIFY critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_SOURCE_IP ikev2_pld_payloads: payload NOTIFY nextpayload CERTREQ critical 0x00 length 28 ikev2_pld_notify: protoid NONE spisize 0 type NAT_DETECTION_DESTINATION_IP ikev2_pld_payloads: payload CERTREQ nextpayload CERTREQ critical 0x00 length 25 ikev2_pld_certreq: type X509_CERT length 20 ikev2_pld_payloads: payload CERTREQ nextpayload NONE critical 0x00 length 5 ikev2_pld_certreq: type RSA_KEY length 0 ikev2_msg_send: IKE_SA_INIT response from xxx.yyy.1.20:500 to xxx.yyy.1.254:55008 msgid 0, 462 bytes config_free_proposals: free 0x1529d4096700 ikev2_recv: IKE_AUTH request from initiator xxx.yyy.1.254:52833 to xxx.yyy.1.20:4500 policy 'jacqueline_iphone_vpn' id 1, 2928 bytes ikev2_recv: ispi 0xd14315b81593285a rspi 0x9f30f9d2ed8dfd11 ikev2_recv: updated SA to peer xxx.yyy.1.254:52833 local xxx.yyy.1.20:4500 ikev2_pld_parse: header ispi 0xd14315b81593285a rspi 0x9f30f9d2ed8dfd11 nextpayload SK version 0x20 exchange IKE_AUTH flags 0x08 msgid 1 length 2928 response 0 ikev2_pld_payloads: payload SK nextpayload IDi critical 0x00 length 2900 ikev2_msg_decrypt: IV length 16 ikev2_msg_decrypt: encrypted payload length 2864 ikev2_msg_decrypt: integrity checksum length 16 ikev2_msg_decrypt: integrity check succeeded ikev2_msg_decrypt: decrypted payload length 2864/2864 padding 14 ikev2_pld_payloads: decrypted payload IDi nextpayload NOTIFY critical 0x00 length 40 ikev2_pld_id: id FQDN/ios.ikev2.myfqdn.com length 36 ikev2_pld_payloads: decrypted payload NOTIFY nextpayload IDr critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type INITIAL_CONTACT ikev2_pld_payloads: decrypted payload IDr nextpayload AUTH critical 0x00 length 31 ikev2_pld_id: id FQDN/ikesync.myfqdn.com length 27 ikev2_pld_id: unexpected id payload ikev2_pld_payloads: decrypted payload AUTH nextpayload CERT critical 0x00 length 520 ikev2_pld_auth: method RSA_SIG length 512 sa_state: SA_INIT -> AUTH_REQUEST ikev2_pld_payloads: decrypted payload CERT nextpayload CP critical 0x00 length 1997 ikev2_pld_cert: type X509_CERT length 1992 ikev2_pld_payloads: decrypted payload CP nextpayload NOTIFY critical 0x00 length 65 ikev2_pld_cp: type REQUEST length 57 ikev2_pld_cp: INTERNAL_IP4_ADDRESS 0x0001 length 0 ikev2_pld_cp: INTERNAL_IP4_SUBNET 0x000d length 0 ikev2_pld_cp: INTERNAL_IP4_DHCP 0x0006 length 0 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 0 ikev2_pld_cp: INTERNAL_IP4_NETMASK 0x0002 length 0 ikev2_pld_cp: INTERNAL_IP6_ADDRESS 0x0008 length 0 ikev2_pld_cp: INTERNAL_IP6_SUBNET 0x000f length 17 ikev2_pld_cp: INTERNAL_IP6_DHCP 0x000c length 0 ikev2_pld_cp: INTERNAL_IP6_DNS 0x000a length 0 ikev2_pld_cp: <UNKNOWN:25> 0x0019 length 0 ikev2_pld_payloads: decrypted payload NOTIFY nextpayload NOTIFY critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type ESP_TFC_PADDING_NOT_SUPPORTED ikev2_pld_payloads: decrypted payload NOTIFY nextpayload SA critical 0x00 length 8 ikev2_pld_notify: protoid NONE spisize 0 type NON_FIRST_FRAGMENTS_ALSO ikev2_pld_payloads: decrypted payload SA nextpayload TSi critical 0x00 length 44 ikev2_pld_sa: more 0 reserved 0 length 40 proposal #1 protoid ESP spisize 4 xforms 3 spi 0x0f9dc45e ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type ESN id NONE ikev2_pld_payloads: decrypted payload TSi nextpayload TSr critical 0x00 length 64 ikev2_pld_ts: count 2 length 56 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_pld_ts: type IPV6_ADDR_RANGE protoid 0 length 40 startport 0 endport 65535 ikev2_pld_ts: start :: end ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff ikev2_pld_payloads: decrypted payload TSr nextpayload NONE critical 0x00 length 64 ikev2_pld_ts: count 2 length 56 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_pld_ts: type IPV6_ADDR_RANGE protoid 0 length 40 startport 0 endport 65535 ikev2_pld_ts: start :: end ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff ikev2_resp_recv: NAT-T message received, updated SA sa_stateok: SA_INIT flags 0x0000, require 0x0000 policy_lookup: peerid 'ios.ikev2.myfqdn.com' ikev2_msg_auth: responder auth data length 510 ca_setauth: auth length 510 ikev2_msg_auth: initiator auth data length 496 ikev2_msg_authverify: method RSA_SIG keylen 1992 type X509_CERT ikev2_msg_authverify: authentication successful sa_state: AUTH_REQUEST -> AUTH_SUCCESS sa_stateflags: 0x0020 -> 0x0030 authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) ikev2_sa_negotiate: score 4 sa_stateflags: 0x0030 -> 0x0030 authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x0030, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: cannot switch: AUTH_SUCCESS -> VALID ikev2_ike_auth: no CERTREQ, using default ikev2_policy2id: srcid FQDN/ikesync.myfqdn.com length 27 sa_stateflags: 0x0030 -> 0x0034 certreq,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) config_free_proposals: free 0x152981361380 ca_setauth: auth length 512 ca_validate_pubkey: valid public key in file pubkeys/fqdn/ios.ikev2.myfqdn.com ca_validate_cert: /C=US/ST=Illinois... in public key file, ok ca_getreq: using local public key of type RSA_KEY ikev2_getimsgdata: imsg 24 rspi 0x9f30f9d2ed8dfd11 ispi 0xd14315b81593285a initiator 0 sa valid type 1 data length 512 ikev2_dispatch_cert: AUTH type 1 len 512 sa_stateflags: 0x0034 -> 0x003c certreq,auth,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x0038, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: cannot switch: AUTH_SUCCESS -> VALID ikev2_dispatch_cert: peer certificate is valid sa_stateflags: 0x003c -> 0x003e certvalid,certreq,auth,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x003a, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: cannot switch: AUTH_SUCCESS -> VALID ikev2_getimsgdata: imsg 19 rspi 0x9f30f9d2ed8dfd11 ispi 0xd14315b81593285a initiator 0 sa valid type 11 data length 526 ikev2_dispatch_cert: cert type RSA_KEY length 526, ok sa_stateflags: 0x003e -> 0x003f cert,certvalid,certreq,auth,authvalid,sa (required 0x003b cert,certvalid,auth,authvalid,sa) sa_stateok: VALID flags 0x003b, require 0x003b cert,certvalid,auth,authvalid,sa sa_state: AUTH_SUCCESS -> VALID sa_stateok: VALID flags 0x003b, require 0x003b cert,certvalid,auth,authvalid,sa sa_stateok: VALID flags 0x003b, require 0x003b cert,certvalid,auth,authvalid,sa ikev2_sa_tag: (0) ikev2_childsa_negotiate: proposal 1 ikev2_childsa_negotiate: key material length 128 ikev2_prfplus: T1 with 32 bytes ikev2_prfplus: T2 with 32 bytes ikev2_prfplus: T3 with 32 bytes ikev2_prfplus: T4 with 32 bytes ikev2_prfplus: Tn with 128 bytes pfkey_sa_getspi: spi 0x5fb0e721 pfkey_sa_init: new spi 0x5fb0e721 ikev2_next_payload: length 31 nextpayload CERT ikev2_next_payload: length 531 nextpayload AUTH ikev2_next_payload: length 520 nextpayload CP ikev2_next_payload: length 48 nextpayload SA ikev2_add_proposals: length 40 ikev2_next_payload: length 44 nextpayload TSi ikev2_next_payload: length 24 nextpayload TSr ikev2_next_payload: length 24 nextpayload NONE ikev2_msg_encrypt: decrypted length 1222 ikev2_msg_encrypt: padded length 1232 ikev2_msg_encrypt: length 1223, padding 9, output length 1264 ikev2_next_payload: length 1268 nextpayload IDr ikev2_msg_integr: message length 1296 ikev2_msg_integr: integrity checksum length 16 ikev2_pld_parse: header ispi 0xd14315b81593285a rspi 0x9f30f9d2ed8dfd11 nextpayload SK version 0x20 exchange IKE_AUTH flags 0x20 msgid 1 length 1296 response 1 ikev2_pld_payloads: payload SK nextpayload IDr critical 0x00 length 1268 ikev2_msg_decrypt: IV length 16 ikev2_msg_decrypt: encrypted payload length 1232 ikev2_msg_decrypt: integrity checksum length 16 ikev2_msg_decrypt: integrity check succeeded ikev2_msg_decrypt: decrypted payload length 1232/1232 padding 9 ikev2_pld_payloads: decrypted payload IDr nextpayload CERT critical 0x00 length 31 ikev2_pld_id: id FQDN/ikesync.myfqdn.com length 27 ikev2_pld_payloads: decrypted payload CERT nextpayload AUTH critical 0x00 length 531 ikev2_pld_cert: type RSA_KEY length 526 ikev2_pld_payloads: decrypted payload AUTH nextpayload CP critical 0x00 length 520 ikev2_pld_auth: method RSA_SIG length 512 ikev2_pld_payloads: decrypted payload CP nextpayload SA critical 0x00 length 48 ikev2_pld_cp: type REPLY length 40 ikev2_pld_cp: INTERNAL_IP4_ADDRESS 0x0001 length 4 ikev2_pld_cp: INTERNAL_IP4_NETMASK 0x0002 length 4 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 4 ikev2_pld_cp: INTERNAL_IP4_DNS 0x0003 length 4 ikev2_pld_cp: INTERNAL_IP4_NBNS 0x0004 length 4 ikev2_pld_payloads: decrypted payload SA nextpayload TSi critical 0x00 length 44 ikev2_pld_sa: more 0 reserved 0 length 40 proposal #1 protoid ESP spisize 4 xforms 3 spi 0x5fb0e721 ikev2_pld_xform: more 3 reserved 0 length 12 type ENCR id AES_CBC ikev2_pld_attr: attribute type KEY_LENGTH length 256 total 4 ikev2_pld_xform: more 3 reserved 0 length 8 type INTEGR id HMAC_SHA2_256_128 ikev2_pld_xform: more 0 reserved 0 length 8 type ESN id NONE ikev2_pld_payloads: decrypted payload TSi nextpayload TSr critical 0x00 length 24 ikev2_pld_ts: count 1 length 16 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start xxx.yyy.15.0 end xxx.yyy.15.255 ikev2_pld_payloads: decrypted payload TSr nextpayload NONE critical 0x00 length 24 ikev2_pld_ts: count 1 length 16 ikev2_pld_ts: type IPV4_ADDR_RANGE protoid 0 length 16 startport 0 endport 65535 ikev2_pld_ts: start 0.0.0.0 end 255.255.255.255 ikev2_msg_send: IKE_AUTH response from xxx.yyy.1.20:4500 to xxx.yyy.1.254:52833 msgid 1, 1296 bytes, NAT-T pfkey_sa_add: update spi 0x5fb0e721 pfkey_sa: udpencap port 52833 ikev2_childsa_enable: loaded CHILD SA spi 0x5fb0e721 pfkey_sa_add: add spi 0x0f9dc45e pfkey_sa: udpencap port 52833 ikev2_childsa_enable: loaded CHILD SA spi 0x0f9dc45e ikev2_childsa_enable: loaded flow 0x1529ef902400 ikev2_childsa_enable: loaded flow 0x1529ef902800 sa_state: VALID -> ESTABLISHED from xxx.yyy.1.254:52833 to xxx.yyy.1.20:4500 policy 'ios_vpn' And, if I run as a daemon, I can see: # ipsecctl -s all FLOWS: flow esp in from xxx.yyy.15.0/24 to 0.0.0.0/0 peer xxx.yyy.1.254 srcid FQDN/ikesync.myfqdn.com dstid FQDN/ios.ikev2.myfqdn.com type use flow esp out from 0.0.0.0/0 to xxx.yyy.15.0/24 peer xxx.yyy.1.254 srcid FQDN/ikesync.myfqdn.com dstid FQDN/ios.ikev2.myfqdn.com type require SAD: esp tunnel from xxx.yyy.1.20 to xxx.yyy.1.254 spi 0x05b906be auth hmac-sha2-256 enc aes-256 esp tunnel from xxx.yyy.1.254 to xxx.yyy.1.20 spi 0xebe5b208 auth hmac-sha2-256 enc aes-256 At the same time, the iphone logs: Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Error>: Not hashing value with class __NSDate Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Notice>: NESMIKEv2VPNSession[Wynnychenko VPN:D636E9EF-3B66-4537-93E8-0E3DEC18D7AB]: Received a start command from Preferences[200] Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Notice>: NESMIKEv2VPNSession[Wynnychenko VPN:D636E9EF-3B66-4537-93E8-0E3DEC18D7AB]: status changed to connecting Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Error>: Plugin com.apple.neplugin.IKEv2 does not have a bundle URL Jun 6 14:54:14 iPhone kernel(Sandbox)[0] <Notice>: SandboxViolation: nesessionmanager(124) deny(1) file-issue-extension target: /System/Library/Frameworks/NetworkExtension.framework/PluginIKEv2.vpnplugi n class: com.apple.vpn-plugin Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Error>: sendInitCommand: failed to create a com.apple.vpn-plugin sandbox extension for /System/Library/Frameworks/NetworkExtension.framework/PluginIKEv2.vpnplugi n Jun 6 14:54:14 iPhone neagent(NetworkExtension)[824] <Error>: Certificate at index 0 could not be created Jun 6 14:54:14 iPhone neagent(NetworkExtension)[824] <Error>: Certificate authentication data could not be verified Jun 6 14:54:14 iPhone neagent(NetworkExtension)[824] <Error>: Failed to process IKE Auth packet Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Notice>: NESMIKEv2VPNSession[Wynnychenko VPN:D636E9EF-3B66-4537-93E8-0E3DEC18D7AB]: status changed to disconnecting Jun 6 14:54:14 iPhone configd[32] <Notice>: network changed Jun 6 14:54:14 iPhone kernel[0] <Notice>: SIOCPROTODETACH_IN6: ipsec3 error=6 Jun 6 14:54:14 iPhone configd(IPConfiguration)[32] <Notice>: siocprotodetach(pdp_ip0) failed, Resource busy (16) Jun 6 14:54:14 iPhone nesessionmanager(NetworkExtension)[124] <Notice>: NESMIKEv2VPNSession[Wynnychenko VPN:D636E9EF-3B66-4537-93E8-0E3DEC18D7AB]: status changed to disconnected, last stop reason Plugin initiated I also note the same behavior (OBSD stating VPN is up, and iOS stating no VPN is present) if I leave the RSA encoded keys in /etc/iked/pubkeys/fqdn/ with the earlier versions of iked (the ones that work with iOS). But when the RSA encoded keys are not present, the iOS<>OBSD VPN works. I hope this report is understandable and complete. If I can help in any way, please let me know. Thank you Ted
