On Fri, Feb 18, 2022 at 11:43 AM I wrote:
> I recently started seeing some ipsec clients fail on newer versions of
> MacOS and iOS. After MacOS 12.1, connecting to my head end now fails
> with NO_PROPOSAL_CHOSEN using mod1024 in my ipsec.conf. I've also
> tried, with no success:
>
> main auth "hmac-sha2" enc "aes" group modp1024
> quick auth "hmac-sha2" enc "aes" group modp1024

Doing further research shows things are just not working out.

I added two different configs that should match in /etc/ipsec.conf

ike passive esp transport proto udp from $public_ip to any \
  main auth "hmac-sha2-256" enc "aes-256" group "modp2048" \
  quick auth "hmac-sha2-256" enc "aes-256" group "modp2048" \
  psk "THIS_IS_MY_IPSEC_PASSPHRASE"

ike passive esp transport proto udp from $public_ip to any \
  main auth "hmac-md5" enc "3des" group "modp1024" \
  quick auth "hmac-md5" enc "3des" group "modp1024" \
  psk "THIS_IS_MY_IPSEC_PASSPHRASE"

Running a packet capture on the server shows that both of these
proposals are being sent by the client and should match in isakmpd.
Alas, they do not.

Here's the pcap -- again, thanks in advance for any assistance.

server# tcpdump -nvvs 16000 -i em0 src host 100.64.10.10 and port 500
13:14:50.662540 64:9e:f3:XX:XX:XX 52:54:00:XX:XX:XX 0800 830:
100.64.10.10.63823 > 203.0.113.1.500: [udp
 sum ok] isakmp v1.0 exchange ID_PROT
        cookie: 197d16ba79870fd2->0000000000000000 msgid: 00000000 len: 788
        payload: SA len: 516 DOI: 1(IPSEC) situation: IDENTITY_ONLY
            payload: PROPOSAL len: 504 proposal: 1 proto: ISAKMP
spisz: 0 xforms: 14
                payload: TRANSFORM len: 36
                    transform: 1 ID: ISAKMP
                        attribute LIFE_TYPE = SECONDS
                        attribute LIFE_DURATION = 3600
                        attribute ENCRYPTION_ALGORITHM = AES_CBC
                        attribute KEY_LENGTH = 256
                        attribute AUTHENTICATION_METHOD = PRE_SHARED
                        attribute HASH_ALGORITHM = SHA2_256
                        attribute GROUP_DESCRIPTION = MODP_2048
[..]
               payload: TRANSFORM len: 32
                    transform: 14 ID: ISAKMP
                        attribute LIFE_TYPE = SECONDS
                       attribute LIFE_DURATION = 3600
                        attribute ENCRYPTION_ALGORITHM = 3DES_CBC
                        attribute AUTHENTICATION_METHOD = PRE_SHARED
                        attribute HASH_ALGORITHM = MD5
                        attribute GROUP_DESCRIPTION = MODP_1024
[..]
13:14:50.667404 52:54:00:XX:XX:XX 64:9e:f3:XX:XX:XX 0800 82:
203.0.113.1.500 > 100.64.10.10.63823: [bad udp cksum 1608! -> 2224]
isakmp v1.0 exchange INFO
        cookie: 3cbfd92c4ea7626d->0000000000000000 msgid: 00000000 len: 40
        payload: NOTIFICATION len: 12
            notification: NO PROPOSAL CHOSEN (ttl 64, id 48652, len 68)
[..]

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