On 2024-12-27 07:25, Jaroslaw Rafa via mailop wrote:
I sent one, literally ONE, and quite important, mail, to Gmail user.

I am using a partial solution, and am cogitating on a more comprehensive solution adapted to my need to reach mailboxes at providers such as Google while preserving mail server independence/sovereignty (definition and reasons below).

TL,DR: create accounts with the problematic services (Google anyways require an account to get access to their Postmaster Tools) and relay your mail through those accounts. Easier said than done, and with challenges / conflicts ahead, but this is my way to deal with the balkanization of email until the problems of anti-competitive nature become sufficiently painful and apparent for authorities to fix.

This post has four parts:

(A) PARTIAL SOLUTION: what I am currently doing that fixed my short-term problem of delivering email to recipients captive of Google/Microsoft-services

(B) MORE COMPREHENSIVE SOLUTION: I have not implemented it yet, because other priorities

(C) DEFINITION: mail server sovereignty. why it is important not to go with the flow (or rather: the tsunami of big tech carried by what economists call network effects) and travel the harder way instead

(D) CHALLENGES/CONFLICTS AHEAD. Because it is strategically important to see things in context. Because big tech is typically at least two steps ahead of government and even one step ahead of the combined intelligence on this list. Else it would not have become big tech in the first place.

Dive in with me, thank you in advance for indulging with the personal anecdotes and opinions sprinkled through the dry tech/biz/law stuff.


(A) PARTIAL SOLUTION: Postfix relayhost configuration

SHOUT OUT to Jarland Donnell, one of the ethical people that make this community so valuable. A while ago I opened an account at https://mxroute.com/ and have configured my self-hosted Postfix instances to relay through MXroute. In main.cf:

   relayhost = taylor.mxrouting.net
   smtp_sasl_auth_enable = yes
   smtp_sasl_password_maps = hash:/etc/postfix/mxroute_credentials
   smtp_sasl_security_options = noanonymous
   smtpd_sasl_authenticated_header = no
   smtp_tls_security_level = encrypt

I use various domains/addresses and MXroute kindly accepts that my server, once authorized as m...@example.com, can send also VERY LOW VOLUMES of emails, including for other domains that I control such as m...@example.com or m...@example.org. I do not know how MXroute makes sure that I really control those domains, and generally that I am not an abuser, but I am certainly not the one who will abuse their generosity. I hate spam, and I hate "legitimate" spam as in: reminders, surveys, how did we do, upgrade your stay, rate us five stars, or whatever else the marketing genius are thinking will make me throw more money at their business and instead just irreversibly waste more of my time.


(B) MORE COMPREHENSIVE SOLUTION: destination-based Postfix relayhost

The above is currently all or nothing. Eventually, I will want to improve, set up multiple relays with accounts on the too big to ignore balkanizing providers and automatically relay based on recipient address through accounts at each specific provider, while maintaining the reply-to: address as my original one. I hoped to find time during this Winter break, but, oh well, priorities, priorities.

For now, I got more than one account and credentials ready -- the usual suspects: Google and Microsoft. But I have not had time to actually connect the plumbing and test (not sure that sending to my own account qualifies as enough testing). I expect some challenges, see further below.


(C) DEFINITION: mail server sovereignty

My business model and requirements are different from yours, YMMV. Below are my specific reasons for my choices to take the harder road less traveled rather than the road big tech would like us all to take. Before my specific reasons, however, some more general ones that may apply to more people on this list, and some jabs at some of the expressed opinions (but not to the people expressing them) in this thread.

Mail server sovereignty is first and foremost the *unmediated* control of my own mailbox; and the protection of the messages I sent from interference of all sorts. I do not need a service provider with interests that are not perfectly aligned with mine.

* competition is healthy. it prevents all of us from being lulled into the complacency of the insiders' oligopoly that leads to stagnation and eventually crumbles from its own rot, not without consequences to users and society as a whole. Anti-competitive forces take many different shapes and forms, including convenient anti-spam filtration that at first sight seems to be based upon statistics and mail flows. Heck, simply based upon statistics and mail flow, Google would be the first sender I would block, but, alas, it has grown TBTB. The point is that even if an act or omission is not directly anti-competitive, if its effect is negative on competition it ought to be reviewed by competition watchdogs and corrective enforcement action may be justified. Keeping the door open to new entrants increases competition. Invariably, new entrants start as tiny little volumes and that's why senders like Jaroslaw have my empathy, my sympathy, and ought to be protected by strategically thinking regulators and industry participants (I may have just typed an oxymoron). Hence the argument that it is anti-competitive to perform some kind of filtering when the result of that filtering prevents alternatives to orthodoxy, such as freebie subdomains on a non-governmental domain that has a track record at being better at policing its users than many TLDs set up according to current orthodoxy.

* freeriding is bad. Freeriding is the offloading of the cost or other negative consequences of one's action on someone else. There is plenty of freeriding in email space, specifically from sender to recipient, including dumping HTML on a recipient with color-blindness or other disabilities, and even just plain preferences. Is sender's content irrelevant or uninteresting to you? oh, just hit delete. Don't like RSI from the delete key? just waste more of recipient's computing cycles, energy, money on ever growing sophisticated filtering and other processing that would not be necessary in the first place if senders were better policed to be more respectful of recipients. I am not proposing to go back to email as it was in the seventies. However, I would like to see better enforcement against senders at their service providers who are currently aiding and abetting the onslaught of annoying "legitimate" email.

* price is information. Until it is not. Shrewd business actors try to make pricing as opaque and uninformative as possible to eskew competition and get away with lesser quality or higher price than transparent competition would dictate. Look at your local airline or the hotels at your travel destination for a total disconnect between price and quality. sadly, you will only find out when it is too late. eu.org may be a high quality service with a communication problem, because its price does not communicate the quality it has compared to some TLDs that offer much lesser quality for a higher price.

My professional reasons:

I am a lawyer and I receive, process, and send sensible information. I have professional obligations to my clients. I hold myself to the highest possible standard, and outsourcing to Google/Microsoft does not qualify. I know I am pedantic: many other lawyers in my jurisdiction simply use Google or Microsoft.

IMHO outsourcing my mailbox and, to a lesser extent, my sent messages to big tech is problematic, starting with the jurisdiction in which the servers are located. Continuing with the (over)reach from the jurisdictions that can exercise leverage on said companies (head office and other multi-national establishments). Last but not least it is problematic in terms of business intelligence (anything from industrial spying, down to the surveillance economy model of harvesting consumer data).

If my client uses Google, I am happy to use Google. If my client uses Apple, I am happy to use Apple. If my client uses Microsoft, I am happy to use Microsoft. But I do not want to add to the mix an uninvited party; nor do I want to monitor so many mailboxes at so many providers. I am proficient about encryption but not all of my clients are, and even just the metadata is sensible enough. To tease the list's imagination with an hypothetical: imagine the initial emails between MacKenzie Bezos and her divorce lawyer were going through your server (and its analytics) before the news made it orderly to the stock market and you had some money to invest in (or divest from / short) her husband's company?

I want control over the email-receiving server. I cannot control what clients are sending, so I control second-best where it is received/stored and who/what has access to it and for what purpose. I can trust the sysadmin I hire/contract and on whom I can impress the proper priorities. Big tech's track record has repeatedly demonstrated that big tech cannot be trusted, and keeps adamantly adding to that track record, as if trying to push the limit of what the world will tolerate. The main reason not to use Microsoft Windows on the desktop these days are the leaks by their screenshooting AI. I know defaults can be changed, but defaults matter, and their model of asking for forgiveness rather than asking for permission has more negatives than positives and in my context it is a recipe for disaster, for which it is difficult to hold them accountable (ever read their T&C? I do).

On the sending side, I am less concerned, because I control the message routing and content.


My private reasons:

My time is my most valuable resource, and it is not renewable. My leisure time is even more valuable to me than my professional time, and I sometimes feel ashamed at how high my professional hourly rate is (and it is still in line and even a bargain compared with similar lawyers).

I like controlling my SMTP on the in-way because I can hard-block the various sources of "legitimate" mail that I have requested not to receive, such as the Qualtrics survey (not singling them out, just the most recent piece of legit spam) that a company I do business with commissioned while overriding my preference for no marketing. They may call it a way to "legitimately" engage with me. I am less diplomatic and call it harassment. I know my stand is on an extreme end of the range and that some in those industries who are here on this mailing list, would find themselves unemployed if everyone was like me. I am unapologetic: all of this marketing is a zero-sum game at best. Does anyone seriously believe that it is a good idea to reach an individual who just got seated at a restaurant following an online reservation with a message "you just got seated at your reserved table at restaurant XYZ?" I personally find it unappetizing, and I even jokingly asked my friend if they see the red laser tracker of a sniper on my forehead. Step back, surveillance economy! Needless to say that the restaurant will not see me again any time soon, and so do other abusers using the same abusive booking system. I understand they have a problem with no-show. Do not punish the rest of us for the no-show and require a deposit on reservation instead.


(D) CHALLENGES/CONFLICTS AHEAD.

The practical challenges I foresee for my model of routing through accounts at the various providers are that they will limit sending from the actual account / their domain. That's the whole point of network effects, attracting participant into the closed system (see FaceTime or Whatsapp). Of course Google/Microsoft will want me to migrate my sending and my mailbox to them and will find some technical way to override my reply-to preference, or just to make it known to the people I am communicating with that they should reach me over there, not at my regular mailbox. See what Apple does to move users from (global) text messaging to (Apple-controlled and subject to the purchase of an Apple-device) iMessage. And of course, said service provider with the freemium pricing model wish they could charge ne for the use, or at least benefit from the flow of information like Meta does from WhatsApp users despite assuring the EU to the contrary when that acquisition was under review.

The conflict of interest is pre-programmed in this one, and it is only temporary until regulators recognize the market-dominant position of big tech and force some form of opening / interoperability. Of course it will be of the clumsy sort like the EU got us used to with the Digital Markets Act, that is likely to result in sub-optimal outcomes such as the USB standard across devices despite Apple's Lightning being a mechanically superior connector; all while forgetting to catch the lower value end of rechargeable electric razors and other such devices that still come with their own wall warts and their own incompatible connectors that make traveling with them so cumbersome.

I will find out if things work out when I test the approach of relaying over the different accounts. Thank you for indulging with my writings. I look forward to read of other's experiences from small operators relaying to Google/Microsoft rather than demanding Google/Microsoft bend over for us.

Yuv
--
Ontario-licensed lawyer


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