On Thu, 12 Aug 2021 11:56:36 -0400, Matt Corallo stated:
>On 8/12/21 09:37, Wietse Venema wrote:
>> Matt Corallo:  
>>> I tried variations of this but never could get it to work - as far
>>> as I could tell the nexthop is fully resolved by the time we get to
>>> the smtp daemon, so there aren't any relevant settings to override
>>> or otherwise set the default on the nexthop there.  
>> 
>> In the FILTER command you specify transport AND nexthop. There is
>> nothing to be resolved BEFORE the SMTP client.  
>
>Ah, thanks. Sadly I'm not sure this solves the immediate issue either
>as it seems to override local domain delivery as well. i.e. it results
>in any of the source addresses which would need proxying to external
>domains being proxied to local domains as well.
>
>For context, this doesn't feel like a crazy setup - some users have
>external addresses they want to be able to send mail as, which we
>(obviously) need to relay via their external providers' smtp with
>authentication. For local-domain mails, there are some providers
>(*cough* Microsoft *cough*) which treat all mail from low-volume IPs
>as spam, no matter what best-practices you comply with, so we want to
>relay anything to Microsoft domains out via a third-party provider.
>
>Its currently working with a second postfix instance and a simple
>socketmap program in transport_maps to lookup if a domain's MX is
>*.outlook.com.
>
>Matt

Have you made any attempt to get your IP 'whitelisted' with Microsoft?

-- 
Gerard

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