Does anyone know what specifically causes this error?

Oct 11 14:14:10 shadesmar smtpd[3086]: fatal: smtpd: bind: Cannot assign
requested address

Means SMTPD cannot attach itself as a listener to the specified IP address and/or port number.

You specified your host name (!) in smtpd.conf, right? Well, I recall you not having your host name in /etc/hosts, which means that your host name's IP address is unknown at boot time. Hence the above error message, I suspect, as SMTPD does not know the IP to bind on.

Up to the time networkd/DHCP is configuring your network interface, SMTPD is retrying to bind itself to the (unknown) interface over and over again - until SMTPD can get an IP address for "hostname", finally.

Try adding a host name to /etc/hosts, then use that host name in smtpd.conf, or try using "localhost" as host name in smtpd.conf. Either way, the above error should go away.

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