I'm trying to get IPsec set up in transport mode using isakmpd, between OpenBSD 6.0, Windows 2008R2+, and i5/OS 7.1. I've already gotten everything working using PSK, but I'd like to use certificates.

I've created a certificate from our CA for each machine. I've put the CA root chain in /etc/isakmpd/ca, the local machine's private key in private/local.key, the local machine's cert in certs/[ip addr].crt, and the remote machine's cert in certs/[ip addr].crt. The certificates have a subject of CN=hostname.domain.com, and a SAN with DNS=hostname.domain.com, DNS=[ip addr], IP=[ip addr].

I'm thinking that I'm just putting the certs in the wrong place. I've run isakmpd with -D A=99, which is confusing because it appears to still be looking in /etc/isakmpd/keynote despite using -K.

Has anyone else used isakmpd with certificates signed by a non-dedicated CA, or see anything I'm likely doing wrong here? Thanks.

Current uncommented lines in ipsec.conf:
ike esp transport from a.b.c.d to d.b.c.a \
        main    auth hmac-sha1          enc 3des        group modp1024 \
        quick   auth hmac-sha1          enc 3des        group none

ike esp transport from d.b.c.a to a.b.c.d \
        main    auth hmac-sha1          enc 3des        group modp1024 \
        quick   auth hmac-sha1          enc 3des        group none

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