On Thu, 26 May 2022, Arete wrote:
My setup: Re-purposed Mac Mini running MacOS 12.4 Monterey, Postfix &
Dovecot, smtp port-forwarded to this box from my firewall. OpenBSD 7.1
running in a VirtualBox machine on the same Mac Mini, with bridged
networking enabled.

insert obvious comment about OpenBSD's ability to run Postfix and Dovecot.
<hopping off soapbox now>

a connection is never made to the Postfix server on the host machine (192.168.20.15:25).

Sounds like a routing triangle. The host machine should have its default gateway as 192.168.20.16 and not the internet firewall. (for other protocols, you could NAT inbound requests to the .16 address, but this is smtp... you want the source IPs for spamd purposes, etc.)

I’m sure there’s something I’m missing, but I
haven’t been able to figure out what. Any insight is most appreciated.

tcpdump or wireshark are a good way to see requests and responses (or
lack thereof)

P.S. dmesg for the OpenBSD VM:

I suggest adjusting your virtual hardware for higher performance/lower overhead:

wd0 at pciide0 channel 0 drive 0: <VBOX HARDDISK>

OpenBSD supports virtio-scsi, much faster than emulated IDE

em0 at pci0 dev 3 function 0 "Intel 82540EM" rev 0x02: apic 1 int 19, address 
08:00:27:a4:36:7c

OpenBSD supports virtio-net, which has lower overhead than a virtualized EM device. You also get much higher throughput with the host

auich0 at pci0 dev 5 function 0 "Intel 82801AA AC97" rev 0x01: apic 1 int 21, 
ICH

I suggest removing the emulated sound card

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