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Attempting to update an old server application (Sympa) to a newer OS. Fun. This includes related services (Sendmail to Postfix). More Fun.

Going through the sendmail.mc, we have

MASQUERADE_AS(`propersubdomain.domain.com')dnl
FEATURE(`masquerade_entire_domain')dnl
FEATURE(`allmasquerade')dnl
MASQUERADE_DOMAIN(localhost)dnl
MASQUERADE_DOMAIN(localhost.localdomain)dnl
MASQUERADE_DOMAIN(actualhostname.domain.com)dnl

The actual hostname is being masqueraded as propersubdomain. The easy fix is changing the hostname. Can't be done.

In Postfix, I am not sure what is the equivalent behavior, or combinations. Inbound, I add the propersubdomain.domain.com to $mydestinations. Postfix will handle everything for propersubdomain.

Outbound, I am not sure. I believe $myorigin would be part of it. But I also see references to generic mapping? Or is it something else?

Which one should I use?

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It's been a long time since I've had to use Sendmail, so I don't recall all the nuances of what MASQUERADE_AS does, but based on a reading of the docs, I'm pretty sure myorigin is what you want ("The domain name that locally-posted mail appears to come from, and that locally posted mail is delivered to").

There is no direct equivalent to MASQUERADE_DOMAIN, but as you suggested, generic maps are what you want to use to achieve the same end result.

Finally, for complete masquerading, you may also want to look into smtp_helo_name.

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