Email encryption is here – use STARTTLS everywhere

They are also the only possibilities to provide proper end-to-end encryption. The last thing we need is another proprietary “standard” (remember how those same companies pushed for drm in the w3c spec).

Yet the only real change can come when end users understand the implications of using the free email providers. I think this is harder for most than using a pgp email client plugin.

More like, relying on SpamAssassin to reliably and correctly classify spam is the anachronism here.

Even if SpamAssassin could do a good job of filtering spam today (which it can't), the set of messages that SpamAssassin classifies as spam will inevitably differ from the set of messages that Gmail classifies as spam, so the only thing this achieves is another point where you have to worry about false positives and training the classifiers.

Furthermore, the problem is exacerbated by poor support of forwarding in modern MTAs. They will queue all received messages first, and when Gmail rejects certain messages during the IMAP session (spam with high confidence, or messages it considers invalid), they result in a bounce, and the thus ensuing backscatter further degrades your mail server's reputation.

The closest thing to correct behavior is Exim's cutthrough delivery feature, which has been implemented "relatively" recently, and even so it is not complete and I've run into issues with it with non-textbook setups.

Oh yes it is. I mean for professional sysadmins it may not be, but try talking any normal person through buying a domain, getting an SSL certificate, attaching that at your MTA, configuring all those fiddly DNS records that prove you're emails are who you say you are. And all of that isn't even taking into account how needlessly painful the actual process of just installing the MTA is.

And what do you have for show from all of that? Still no real assurance that half your mail won't end up in spam, no web front end (that step alone adds several additional layers of complexity), less guarantees regarding up time (since you no have a single server that you need to manage yourself), arguably worse security (since you're now asking a layman to harden a Linux box) and the whole thing comes with a heftier price tag than Gsuite.

We're not talking about self hosting an IRC server or other service you can throw up in an hour and then forget about. Email is a frustrating sequence of a multitude of steps where even just one of them could render your set up worthless. Hence why even many of us sysadmins have long since given up self hosting email servers. It's just not worth the effort

The big players (Google, in particular...in case it's not clear, the bulk of this rant is leveled at Google; Microsoft is an offender on perhaps 25% of the level, Yahoo just doesn't seem to care) have ZERO interest in "playing nice" with small e-mail servers. My experience running my own e-mail for almost twenty years then finally throwing in the towel and migrating to Fastmail not only proves this for me, but is, according to other sysadmins I've talked to, quite common.

I did everything right when hosting my e-mail. I did it for myself and maybe four others. The volume of mail going out of my server was so low, I could read the outbound mail.log for myself, and routinely did. Every domain had SPF, DKIM, and DMARC records. The outgoing single IPv4 and IPv6 addresses I used had perfectly-matching forward and reverse DNS lookups. I had a script that checked every blacklist I could find every 24 hours. My IP addresses were allocated from my (professional) colocation provider and SWIP'd to me with valid contact information. My IP addresses had been unchanged for seven years and had been stable for ten years prior to that change. My colo provider had a draconian non-spam policy. Nobody ran an e-mail list or anything. I've used the exact same domain for e-mail for over twenty years.

Still, every couple of months, Google (sometimes Microsoft, but far and away most likely Google) would decide to simply stop delivering messages from my five users--remember, including me--to Google's users. The messages would just...disappear. Sometimes, Google would stop delivering the messages mid-conversation. Replies would be going back and forth but then my reply to a Gmail user would go to /dev/null while their messages to me would still arrive. Most of the time, the mail would go to spam (even with that little yellow tag meaning "verified sender" or some such) but 20% of the time the mails would just disappear.

Worse, the destination would say "250 OK" to every e-mail I sent them so I had no way of knowing that the messages had been sent to the big bitbucket in the sky. I got annoyed.

I signed up for Google's Postmaster Tools and Microsoft's similar offering. Microsoft would at least show me telemetry but it wouldn't do any good. Google? Google would proclaim that I wasn't sending them enough e-mail so I couldn't show up on the dashboard.

Finally, after three years of fighting this, it came to a head when I was, at all places, at a boardgame meetup during one of these "blackout periods" and got introduced to a Google SRE who worked "adjacent" to Gmail. "Oh, hey, you should talk to techsupporter, he does e-mail too!" was the opening line. We talked, I ranted, and he actually said he'd try to help. He escalated internally and the word came down from on high on their SMTP team or some such: "domain [mydomain] has insufficient reputation."

What did that mean? Apparently, their system--at least at that moment--thought my domain was "too new" and they tilted towards just binning the e-mail. I got red, saw stars, then gave Fastmail $390 for three years of service on three e-mail accounts and moved everything to them within five hours. That was the last straw, the final injustice. For me, the "decentralized Internet" died on that day.

Why was I so pissed? Observe these dates from WHOIS:

    Domain Name: MYDOMAIN.ORG
    [...]
    Creation Date: 1997-03-10T05:00:00Z

    Domain Name: GOOGLE.COM
    [....]
    Creation Date: 1997-09-15T04:00:00Z