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So frustrating that many gmail users are unaware that emails from small independent mail servers are regularly dumped into spam, have attachments and/or links dropped, and then get annoyed at me for it. Especially in non-tech circles, they often don't believe it's even possible.

@o0karen0o gmail anti-spam measures are so "good" because they aggressively scrub emails with little regard to false positives. Based on my experiences hosting my own email servers for over 20 years I am convinced Google believes email should be a centralised service provided only by the tech monopolists...preferably only them.

Running an email server these days is actually pretty easy. The ONLY hard part is jumping through the ridiculous hoops put up by gmail and to some extent Microsoft's email services...almost all of which do next to nothing to mitigate spam.

@msh @o0karen0o At my previous job, we use gmail, using the employer's own domain. All mail was sent via gmail, using authentication, even if sometimes not via the web interface.

I had one co-worker whose emails usually, but not always, ended up in my spam folder, regardless of their content. Never did figure out why.

@liw @msh @o0karen0o My money's on “person's name has a hash collision with spam from 2008”.

@msh @o0karen0o in my experience Microsoft is actually a lot worse in that regard. But I don't think it matters much difderenciating between terrible and " really, really terrible"...

@Bubu @msh @o0karen0o yeah, mirosoft just silently drops emails from whole domains. You will never know someone tried to send you that email. Not even in the spam folder.

@msh @o0karen0o Echo'ing the MS is way worse than Gmail sentiment. With DKIM etc properly set up I've never had issues getting something to a Gmail user. Sending mail to Outlook.com users though, forget it.

@michael @o0karen0o yeah they are both awful, though MSFT is the clumsier of the the two, employing pretty blunt instruments like IP blocks and draconian RBLs. I wouldn't be surprised if they eventually block the IP ranges of all the VPS and public cloud providers by default as they think nobody has any business hosting email without their own data centre.

Google is frustrating in other ways. It isn't too bad to get the DNS incantations right for DKIM, SPF etc for delivery to be accepted but where messages are delivered to can sometimes be a complete mystery that even Google employees aren't even certain of. Is it Junk? Is it "promotional"? what is it?

Only the algorithms know.

Also I suspect BOTH of them don't like Hurricane Electric 6in4 tunnels and the like (just as Cloudflare has started to hate on them). The issues got bad enough that I've had to retire my 6in4 tunnel until I get native ipv6 fibre service in the coming weeks.

Anyways I recommend avoiding both, they are both absolute trash services.

@o0karen0o @bady

Sounds like Facebook=internet.
Same with UPI. Most of my friends don't know it is interoperable. When they sent money, they insist for a private player app, I shown them it is possible to sent money without having the same app

@o0karen0o It is frustrating.

If I had a penny for every time someone has said "have you checked your spam folder" I could buy a ☕ and a 🥯 and have some 💰 left over.

I wonder how that ship can be turned?

Would encouraging the use (and support) of email clients instead of webmail help people realize how email is not a platform?

@edsu @o0karen0o Google is way ahead of you, it's officially difficult to set up standard IMAP clients with Gmail now. And I think admins in managed Gmail accounts can forbid it entirely.

@seachaint @o0karen0o It has never been easy I guess, with acronym soup (IMAP, POP, SMTP, TLS, what what)? But instructions can usually be found if you are persistent?

As a point of reference, I got a new work laptop recently (MacOS) and spent a bit of time getting Mail to talk to my personal Gmail, my work email (Exchange) and my Pobox (now Fastmail) and it worked. I couldn't seem to convince my Android FairEmail app to talk to the work Exchange though, so your point stands.

@seachaint @o0karen0o
Maybe if more people demanded that it work it wouldn't erode away? But it seems like the security threats around email are aligning with moneyed interests to shut off client access, not open it up.

@edsu @o0karen0o Pity there was never a widely used standard for "packaged server settings", so you could just provide people with a little settings file and let them pick a client, load settings, log-in as usual.

@seachaint I know some clients seem to be able to autodetect settings, but I always assumed that worked because the client recognized the corporate platform behind the domain somehow? A little standard for packaging up the details would be super useful.

@edsu Actually I have no idea how that works. I assumed it was basically a limited port-scan followed by a STARTTLS handshake attempt or something.

But now I wonder whether a DNS based solution could work even better - package login settings in a TXT record so clients can fetch them from nothing _but_ login details? (with username being full email address)

@seachaint yes I was immediately thinking the same once you mentioned it; kind of like how SPF works? en.wikipedia.org/wiki/Sender_P

@edsu @seachaint @o0karen0o There's now a protocol for making logging in via a native client easy: you can download a standard configuration over HTTP on supporting email hosts.

Unfortunately clients & servers which support it are rare. So doesn't help much yet.

@edsu @o0karen0o Besides: There's zero hope for usable end-to-end encryption whilst most everyone's using webmail! Though it'd still be hard once email's moved off of the web...

@o0karen0o Which is why I usually refuse to exchange mails with Gmail accounts. If someone writes me from one, my mail server auto-responds suggesting them choosing a different mail provider – with a link to details and a note that I'll probably not respond.

@o0karen0o
I have two customers @ Gmail. My e-mails to them end up very often in the spam folder.

@o0karen0o email is a great example on how to centralize a decentralized network

@o0karen0o one of the issues I've come across is that if you host your own mail server and your residential ISP just happens to be on some random black list (almost all of them), you will never have reliable email. The solution is to pay out the nose for a "business account" which all you're doing is changing your dns to a non-generic one. Apparently this service is worth $100+ extra a month. For one little PTR record change. It's a massive scam.

@minnix
It would be cheaper to get. Vps service then to run your own mail relay on or vpn.
@o0karen0o

@o0karen0o
I’ve had the same issue with Exchange servers as well. I am a sysadmin in a computer science subject organization and I have heard these comments many times. It is almost common ”knowledge” that it’s impossible to run your own mail servers because ”it is just too difficult”

But all servers servers I’m responsible of score 10/10 on mail-tester.com and quite often sent mail will still end up in spam folders among gmail and outlook recipients

@o0karen0o just set up your mail server properly and no problems. never had problems with delivery to gmail.

@o0karen0o someone: "Email is email, it just works, Google wouldn't be able to just meddle in everything!"

Oh my sweet, sweet summer child. They can. And they do. Somehow my server hasn't been confined to /dev/null... Yet.

@o0karen0o

Some of the largest US ISPs block e-mail from basically anywhere except a small number of "known" origins (other big ISPs, Gmail, MS…).

@o0karen0o @brainwane I’ve had occasional issues with all the big providers, but gmail has been the worst for years. Bad false positive rate, minimal feedback, mediocre remediation options.

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