sending emails to @gmail.com

[rrq]

This morning I got a blurb here about the pains of sending emails to addresses @gmail.com, detailing a bit about how finicky they, Google, are.

Whilst that is true, I've held this email address some 20 years mostly because their spam filtering has been quite outstanding. During that time I have set up some number of MTA (typically small and smallish ones), and like apparently this forum, come to realize both that in order to deliver to @gmail.com addresses all the "ducks" need to be in perfect order, and that getting attention and assistance by Google staff to figure out the "ducks" is near impossible.

This forum is close to perfect in its setup apart from lacking its reverse DNS setup, which I believe is one of the "ducks", i.e. one thing that @gmail.com is finicky about.

(And if it'd be of any help. I'm more than happy to be a trial target for MTA configuration trials.)

[itistoday]

Alas, even our reverse IP is setup correctly. Results from check-auth@verifier.port25.com:

Code Select Expand

==========================================================
Summary of Results
==========================================================
SPF check:          pass
"iprev" check:      pass
DKIM check:         pass

It is just Google being Google, trying to destroy the Internet's decentralization.

[rrq]

Ah; I looked up rDNS for 168.235.93.184 and got 168-235-93-184.cloud.ramnode.com rather than newlispfanclub.com, which would be the origin of an email.

[itistoday]

Yeah the reverse IP is based on the mail server which is a different machine and domain.

[rrq]

Yes, the MTA setup would be fine, but afaik gmail will want the original sender (newlispfanclub.com) to have rDNS set up (as well), especially for resolvable hosts "without history".

[itistoday]

Hmm. Well, I self-host email for multiple domains. This is perfectly normal.

If Google for some inexplicable reason wants people to host an entire mail server for each domain they own, they should consider how bad for the environment that would be.

The whole concept of having a reputational history is also rather dystopic. How are people supposed to spin up new mail servers? EDIT: maybe it wouldn't be so bad if all new mail servers started with a perfect reputation.

I thought Google engineers were supposed to be smart? I'm sure, if they want to "not be evil", they can figure out how to handle spam without destroying the fabric of the Internet.

In the meantime these providers manage it just fine, and without spying on their customers:

- https://tutanota.com
- https://www.startmail.com
- https://lavabit.com
- https://protonmail.com
- https://www.fastmail.com

[rrq]

Well, I'm not trying to support any of Google's business practices; just trying to assist in getting the forum emails delivered to @gmail.com addresses (especially since I happen to have one).

And for that I believe it would be good getting the rDNS sorted for newlispfanclub.com.

[itistoday]

And for that I believe it would be good getting the rDNS sorted for newlispfanclub.com.

The only way to do that would be to setup a dedicated email server for newlispfanclub.com, which I'm not going to do because it would be setting a terrible example for how people should react to Google's bullying.

Instead, we've explained the situation in the registration text for newcomers while sharing Gmail alternatives. I'm doing this on the forums for my small business as well.

[rrq]

Eh? Doesn't your ISP provide rDNS setup?

EDIT: it's not related to email as such, and I agree that setting up your own MTA would be too much.

EDIT 2: not sure if relevant:
https://clientarea.ramnode.com/knowledgebase/19/How-do-I-set-reverse-DNS-RDNSorPTR.html

[itistoday]

Ah I see what you're saying!

OK, so yes, as I mentioned the rDNS for the mail server is correctly setup to point to the mail server's domain.

However the rDNS for the machine hosting this website doesn't currently point to anything as you pointed out. So yes that's something I can fix - just did that. I don't know how long it takes to propagate, but hopefully should be showing newlispfanclub.com soon. We'll see if that helps with @gmail.com. (EDIT: I will be surprised if it does, because it's a completely different IP from the IP that Gmail sees for the mail server.)

Still, it's very common for one machine to host dozens of domains, and per-machine the rDNS can only point to one of those domains. So this isn't something Google should be checking for when handling email.

Proper spam prevention should not rely on such things IMO, but rather they should use machine learning / deep learning to classify messages. I'm honestly surprised and disappointed that we don't have a good open source solution to this yet.

[itistoday]

(EDIT: I will be surprised if it does, because it's a completely different IP from the IP that Gmail sees for the mail server.)

Indeed it doesn't seem to have helped. But I guess it was worth a try. 

[rrq]

Au contraire I, at gmail.com, got the notification email from this forum today. Which is great. Something got improved ...

[itistoday]

That's great news!