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Date:      Mon, 1 Mar 2021 11:41:28 -0600
From:      Tim Daneliuk <tundra@tundraware.com>
To:        FreeBSD Mailing List <freebsd-questions@freebsd.org>
Subject:   Re: Totally OT comment: Re: Somewhat OT: Mail Relay Services
Message-ID:  <8dc26e45-355a-dadd-0309-02dda1da3d87@tundraware.com>
In-Reply-To: <2edd9853-3af7-c0b8-7118-329d8af346be@kicp.uchicago.edu>
References:  <877d08ef-d533-69f6-4c44-f2cbbe39ba31@tundraware.com> <3926E240-2226-4E94-96E2-10A877B139D0@kicp.uchicago.edu> <3dac8dd5-7751-1823-3cfc-45172cd77b64@FreeBSD.org> <2edd9853-3af7-c0b8-7118-329d8af346be@kicp.uchicago.edu>

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On 3/1/21 9:48 AM, Valeri Galtsev wrote:
> 
> 
> On 3/1/21 9:30 AM, Matthew Seaman wrote:
>>
>> Having worked for an e-mail service provider in the past, I can state that it isn't GMail, Outlook or any of the other big cloud providers intentionally killing off personal e-mail servers.
> 
> No, they are not. It is not they, but their way of doing things does.
> 
>> Well, other than by competition: providing an easy-to-use mail service with little administrative burden.
> 
> Leaving people switching over to "big boys" along, I am considering purely technical aspects of "small time" servers being thrown out of the ability to reliably and consistently providing email services, - because of the way bug boys do things.
> 
>> It's the continuing arms race between the Spam senders and the Spam filtering.  Reputation scoring based on sender IP is one of the best tools in the box for filtering spam, but...
> 
> Yes, and your "BUT" is exactly why I called "barracuda" and friends a brain dead approach. Do we still support mail forwarding? Do we still consider email account owner entitled to receive all mail arriving for his/her account? If both answers are yes, then your server quite likely will be "barracuded".
> 
> Just my $0.02.
> 
> Valeri

I agree with all the above, but I think there is a bit more to it as well ...

The BTAE (Big Tech Axis Of Evil - Google, Facebook, Twitter, et al) don't just host
services people want, they harvest at least the metadata about how those services
get used (and probably some of the data itself, no matter what they say).

email is always going to be a 'postcard' - anyone along the delivery chain can peek inside
the envelope if they really want to.  Even if - as I have done - you host your own domain
on a cloud provider, or even a physical server in your premise - the moment the mail goes into
flight, someone, somewhere is logging it with the potential ability to harvest it.

The question, though, is who is more able to make use of your content?  An mail relay company
of relatively small size, or Google with its billions and advanced tech?

Even when I ran my own mail services at a static IP I controlled, it was a losing
game.  When there were reputation questions, trying to get any of the blackholing
services to pay attention was a major pain.  Some of the smaller ISPs were
equally disinterested because SPAM management was just overwhelming them.

So, for now, I've settled on a compromise - I will run our own email servers and the policies
around them will be under our own control.  But for purposes of external delivery, I am
now using a 3rd party so that the reputation issues (and resolution) accrue to them.
We'll see how this works.

P.S. This did force me to get off my lazy butt and finally get DKIM and DMARC properly
     configured ...



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