#GMail is harmful to e-mail ecosystem; its antispam blocking policy matches too many valid messages as spam.
It blocked LastPass email leak warning email, because it contained "a link" to a leaked site.
It blocked an e-mail from goverment agency addressed directly to me.
It discriminates all non-gmail servers, and it's pretty much impossible to own a private SMTP server these days, because GMail will classify everything as spam.
It's not how e-mail should work.
Consider dropping GMail.
@lschuermann @antekone I've been running my own mail server for about 15yr now, and I'm finding that sending to G,MS etc servers is actually working very well nowadays, but you do have to ensure you're config is rock solid including rDNS, IPv6, SPF, DKIM and DMARC. Use a tool like mxtoolbox.com to ensure your server's IP is not blacklisted anywhere, and a tool such as mail-tester.com to analyse and report on the email your server sends.
@aran @antekone Yeah, I'm running mine for a few years now and with the big providers (which *know* how to do Email correctly but sometimes deliberately decide to fuck things up) I never had an issue. Its medium to large company's sysadmins which apparently don't know that services other than their domain and the big webmail providers exist. Even worse, I've got my MX on a subdomain (with is.currently.online, that's a must :D).
@aran @antekone @lschuermann you must be using a static IP, which makes a huge difference. Of course by bending over backwards to send to #MACFANG corps, you end up supporting them. I will not, so I run my mail server on a dynamic IP and refuse to email MS/Gmail/Yahoo recipients. I tell them get an ESP that works if they want mail from me.
@lschuermann @antekone @aran The only way that I'm willing to email a #MACFANG user is by old fashioned #FAX. If they have a fax#, then I can send a fax to them without touching their freedom-hostile tech giant, in which case their FAX provider sends a digital image of my msg to the MS/Google/Yahoo server.
@aran @lschuermann @antekone I have no issue in general with delivering to gmail but MS seems to hate my email. Not sure why as I have all the dns stuff setup and passing..
@PeterSanchez @aran @lschuermann @antekone MS has always been more finicky. Gmail pretty much works, even without SPF, DKIM or DMARC (all optional), despite urban legends to the contrary. MS used to have a lot of problems - even deploying servers themselves with broken rDNS etc. However worst problems I've encountered have usually been with techies running their own misconfigured mailservers - it's hard, documentation is lacking, and misinformation is everywhere (eg. "SPF is required").
@dentangle @aran @lschuermann @antekone I have SPF but don't believe it's required. Honestly if DKIM passes, I don't get any other reason for it not to be delivered.
In my case, I find that signing my emails (which is by default) seems to trigger outlook online and on desktop. Sometimes I just don't sign a message when I know it's going to a MS / outlook using recipient.
@aran
I thought that I could mail gmail users to. But I only have a few contacts on gmail. Recently I had to mail a new contact on gmail and.. ended up in his spam folder.
My server has all the bells and whistles, and a score 10/10 on mailchecker.
@lschuermann @antekone
@antekone it also blocks sometimes legit emails from Debian without any reason given. not nice :(
@antekone Gmail sucks, more than ever today. @Tutanota or @protonmail all the way.
@tapaniraja @antekone @Tutanota @protonmail You might take a look at https://posteo.de/en/ and https://mailbox.org/en/ also?
@svenbrier @antekone @Tutanota @protonmail Yes, familiar with both. Great alternatives as well.
@tapaniraja @antekone @Tutanota @protonmail
I don't have any experience with Tutanota, but unless you're using Protonmail for hosting with a custom domain, I strongly recommend against it.
Their encryption setup means that they can't forward emails to another address, making it extremely difficult to leave.
I'd recommend going with a more traditional email or mail hosting provider like Posteo, Fairmail, of Migadu
@th4lia @tapaniraja @antekone Hi there! Although automatic forwarding is indeed not possible with ProtonMail at the moment, paid users can use the Import-Export app to easily export their entire mailbox in the event of a migration: https://protonmail.com/support/knowledge-base/how-to-export-emails-from-your-protonmail-account/
@protonmail @tapaniraja @antekone Import and export are a non-issue for anyone with a decent mail archiving workflow. The problem is that there is no easy way of watching for mail going into the old account without maintained a payed account or staying signed in to the browser or app.
This makes it *really* difficult to switch providers
@antekone The links the send in the reject messages also point to "help" pages that are not helpful and not telling me what they want to see, e.g. https://support.google.com/mail/?p=IPv6AuthError doesn't mention IPv6 at all...
@cm @antekone Speaking of GMail's IPv6 support: even with perfectly configured IPv6 FCrDNS, DMARC, SPF, DKIM, ADSP, etc., Google keeps randomly rejecting e-mail sent using IPv6. Only option: force all outbound e-mail aimed at Google to be sent to a hard-coded IPv4 GMail inbound relay, overriding their DNS. Very clean & convenient... 😕
@antekone The problem with the email service provider market is that people choose their one provider for life. It takes too much time to change hundreds of online (and offline) accounts that have the old address. Most people don’t have a record of who has their email address so they don’t even know who and what needs their new address. This protocol-level vendor lock-in allows for unchallanged abusive policies and hurts competition.
@antekone Longer-from reply at https://www.ctrl.blog/entry/email-identity-provider.html
@antekone I agree with you on most points but "pretty much impossible" does not fully match my experience. I manage my own SMTP server and I interact with Gmail people.
@antekone I completely agree! Consider dropping GMail in favor of some smaller provider (not Yahoo or the likes) - there are many remaining and doing a great job in keeping the Internet as open as they can.
@Ventronik @antekone I really like mail.de for example.
@antekone
Yes, definitely. You should drop it.
@antekone Google provides the dominant service in a number of areas now and shows in all of those areas that if you dominate the market you don't need to provide good service. In many cases the main feature they provide over the competition is unlimited space.
@antekone Okay.
For what?
@antekone gmail should have stayed garfield mail
@antekone Bonus, almost everyone bulk drops any "residential" IP.
@antekone
Drop Gmail. Only use for the account here is for login authentication on Google -powned essential infrastructure. The ASB Bank, for example, now insists on a Google account for NFC payments.
@antekone did that yrs ago.
@antekone is go so far as to say that Gmail isn’t Internet email, and I suspect that their system isn’t even SMTP standards compliant (though I haven’t had a chance to prove that yet).
It’s like any myriad of old proprietary email systems (AOL, Compuserve, etc.), and you’re right, it’s making its users more and more undeliverable.
@antekone Well, I turned that horse around: my mail server auto-responds to mails from Gmail, telling the sender that I won't (and that they should get themselves a "real mail provider" that respects the privacy of their correspondents).
@antekone outlook.com has similar issues. It blocks whole IP ranges (e.g. the whole Hetzner IP space) and drops or bounces mails from there (sometimes even silenty).
@antekone Goog seems to put emails from SDF accts in to spam now.
This problem is bigger then most realize. Tons of companies now outsource their email to goog (or outlook) because they get tired of fighting to say off blacklists. Just because it isn't "@gmail.com" doesn't mean it isn't powered by Gmail. You can get yourdoamin.com powered by gmail.
Goog & Outlook.com basically run a protection racket today. Hire them for your email hosting or risk having your domain labeled as spam. 😡
@antekone this happened to me when using Mailbox.org with custom domain. My mails were considered by spam by Gmail recipients.
I managed to solve this with proper SFP and DKIM configuration.
@antekone I eventually want to move to a different mail provider, maybe s9mething like mail.com which is end to end encrypted...
@antekone it's increasingly seeing more adoption among corporates. For commoners, there's nothing better than free 
This seems a bit hyperbolic. Gmail isn't the reason that self-hosted email servers are increasingly difficult to manage. Spammers and the necessary security responses to them are the reason why most people can't keep up.
@ScottMortimer @antekone the anti-spam response is way overblown & the unnecessary colateral dmg to legit senders is what broke email. The excessive block-all-dynamic-ip approach is very convenience for large providers who want everyone to depend on them anyway.
Niklas
@antekone You're so right,delete that shit.I deleted my Google account years ago and haven't missed it a single time.There are so many good,privacy-respecting and free email providers.If you need one,here are the best: https://tutanota.com , https://dismail.de and https://disroot.org
@antekone The Google argument would be: "if everyone just used Gmail, this wouldn't be a problem."
I'm with you on this, but a couple of thoughts: 1) is this also a problem with G Suite email? and 2) What are the best alternatives to Gmail in your opinion and based on what criteria?
@antekone All links are changed to tracked ones as well.
@antekone anti spam measures can be discriminating, but gmail is a whole new level💁
@antekone and don't drop Gmail for an Outlook/Exchange Online system: they do exactly the same thing. Any SMTP server that is not run by an ISP or a giant mail hosting company is flagged as spam by default.
This is blatant anti-competitive behaviour, but they will claim it is for our own good.
The reality is that they want to control your data and lock you into the privacy nightmare that their ecosystems are.
It is AOL/CompuServe all over again, only much, much worse.
@kicou @antekone that an important point. #Microsoft is actually worse than Google, as MS blanket rejects all dynamic IPs, whereas Google is hit-&-miss (or least that was the case back before I started a full on boycott of both)
But you're completely right: drop GMail (and all other Google services, for that matter).
@antekone fwiw, Microsoft's mail (e.g. outlook.com) is even worse -- it was silently dropping my messages (not even filing them as spam) for several years before I thought to do a "delivery status notification" on one of them, and finally got an error message back.
This caused me to believe that a very dear friend was intentionally ignoring me, which could have resulted in us losing contact if I hadn't investigated further.
It even spams messages from GMail, though at least it doesn't silently delete them.
cc @resist1984
@antekone Another horrible related thing that's starting to happen a lot is that many email sysadmins are getting lazy when it comes to spam set up and simply rejecting all incoming messages from any mail servers that aren't google, ms etc which helps to cement their monopoly even more 😞