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by em-bee 874 days ago
this doesn't seem to help for private email.

i want to send email to my friends at google. yet google blocks delivery.

this is not any kind of business or commercial messages. but from my private account to my friends account.

SPF and DMARC check out and surely private emails should not need unsubscribe headers. so your site says everything is fine. then why does google still reject my emails?

4 comments

This really getting crazy. My daughter nearly did not get into the swimming course because google just black holes the registration confirmation because my wife's used her Gmail.

I really hope that this kind of stuff gets illegal: just taking an email and virtually burning it.

this really sums up my feelings. i have sent emails to people past that i have no other way to reach and never got a reply, and i have no idea if they even got my email.

and the same the other way around. which is one reason why i run my own server.

i always believed that spam filtering must be done at the end user, and noone else has the right to block email from reaching me. in particular the most obvious thing, every address that i send to, should automatically be whitelisted as a valid sender, unless i explicitly mark it as spam. the exceptions should be obvious DMARC/DKIM/SPF violations.

at one point i was even working on my own email server to implement this kind of whitelisting/filtering myself.

My social group has been shifting away from using the internet-wide email system to using a private one just among us that we run. It works well in my group because most of the emails we send/receive are amongst ourselves anyway.

All of these antispam measures are fighting a losing battle -- every one of them reduces the utility of email and are only (barely) acceptable because spammers reduce the utility of email to an even greater degree.

By running our own email system that doesn't interconnect with the internet's, email has become actually useful again.

Hah... somehow i have this feeling that we are heading right back into the "good old days" of separated BBS networks, some commercial, some private, but none of them interconnected.

Somehow i like the thought of this...

We've already done this. In effect, we're running a private "internet" that uses the public internet as one of the communications channels, but does not interact with any internet servers beyond that.

It's really beautiful and freeing to have an "internet" that works really well, even if it is a very tiny one.

But running an email system that does not connect to the wider internet also ruins the idea of email as a globally reachable address. Everything is a trade-off :-|
True, but I think the days of email as a globally reachable address are already on their way out. It's not exactly unheard of for some people to be unable to send email to addresses hosted by some common mailservers (including gmail) right now.

However, none of my friends use our mailservers exclusively. They also use the internet mail system. But having our own means that we don't have to worry about deliverability issues, spam, or any of the other problems that exist on the public system.

IP-based rejection may be the answer. You may not be doing anything problematic but if your IP neighbors misbehave, your IP will be blacklisted too.
i am considering that, but it has worked before, and i have this same IP for years now. (i am not 100% certain, but i am pretty sure i already had this same IP when it did work)

anyways, my suggestion here would be that an IP check would be a feature that mailready.info could include.

> then why does google still reject my emails?

Multiple options. For example, your IP address may not have a good reputation. This can happen when a previous tennant used your IP address to send spam, but it also happens when you send very little email to Google/Microsoft servers, not giving you the opportunity to build a good reputation. I briefly considered sending my mail server logs to Gmail so I could get regular whitelisted email delivered, but I changed my mind when I realised Google would probably mark my domain as a bot.

This seems particularly bad on IPv6 for some reason. I'm not sure why, maybe it's because their spam filters are treating every address as a /128 rather than a /64 network?

The worst server in my experience is Microsoft Exchange. I caught the stupid platform taking my email, _rewriting the email address because it didn't like it (despite being compliant!)_, and _then_ checking the DKIM signature, which obviously failed. It doesn't have IPv6 deliverability issues, though, because like many Microsoft cloud products, it doesn't even support IPv6. Microsoft Outlook also sometimes fails the SPF check... because of DNS issues _on Microsoft's side_.

None of this is standards compliant, of course. The best you can do is DKIM+SPF+reverse PTR+strict DMARC+DNSSEC+DANE+using some expensive data center so there aren't many spammers in the nearby IPv4 blocks. Most of these can be generated automatically through online tools or ready-out-of-the-box email servers such as Mailinabox or Mailcow.

Also, _check your configuration regularly_, set up alerts or something; sometimes something may break and your domain/email address will start losing reputation.

It's infuriating to get email delivered, even if you do everything right. I've given up on that stuff, though, and tell everyone I email to check their spam folder and move it to their inbox to train their spam filter.

when you send very little email to Google/Microsoft servers, not giving you the opportunity to build a good reputation

this is something i find really frustrating, because, how am i supposed to fix that?

it's a personal server. there simply isn't that much outgoing traffic. and then, because google rejects my emails i have to use a different server to send mails to gmail.

so how exactly would i generate that neessary traffic that unblocks me? (this is kind of a rethorical question, i don't expect a real answer here because i don't believe a real answer exists)

should i write every email twice? from two different senders? i feel that would make the emails even more suspect than making things better.

send fake emails? that would be like sending spam in order to convince google that i am not sending spam.

seems to me that if low traffic is really the reason then there is no hope, and all i can do is to give up, which for now is what i did.

Exchange is an abomination. A few hours trying to do something with groups was enough to see that for me. As a QA I would reject it until 100 or so bugs were fixed (that I saw in a few hours of use, so maybe 10k+ bugs total?)