> Your firewall could prevent smtpd from starting if you have a default "drop 
> all" rule, then you start smtpd and finally your firewall loads the correct 
> rules.
> I had a similar problem in the past due to that and an incorrect hosts(5) 
> file. 
>    Cheers
>      Giovanni

I've looked through my startup logs and picked one of the
latest-starting services I had and set the smtpd service to start after
that, but it didn't make a difference. Even the repeated start attempts
are all failing. The repeated restart attempts are quite a bit after the
rest of the system starts up, so I'm really not sure what it could be.
Again, it starts with no issues if I start it myself.

Does anyone know what specifically causes this error?

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

Again I appreciate all the helpful suggestions thus far.

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