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Major European payment processor can't send email to Google Workspace users

atha.io

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Re: Major European payment processor can't send email to Google Workspace users

#162
post #69

Earlier quoted context omitted.

I think it's the latter. But, in either case, you're right in that you get the same result. Now, let's assume that if it is the latter (it's spam related), and Google were to accept the message, but then internally bin the message, it would be worse. At least in this case, they are bouncing the message. Because of this, the sender is at least aware that the message wasn't delivered. Also, the author was able to get t…

In my experience, email is an unreliable way to communicate any time-bounded critical information. When I want to be sure an email was transmitted on either side, the only reliable way to ensure this is to use a distinct channel to validate reception and confirm content. That is, when some hotline tell me that they just sent and email with the information, I ensure they hold the line until I got the actual email and…

Email is an unreliable way to communicate any information, in the strictest sense of the word "reliable." The protocol does not guarantee that any email will be delivered, nor does it guarantee that failure will be detected. It's a good-faith effort. The bits could drop on the floor at any point and you might never know.

Re: Major European payment processor can't send email to Google Workspace users

#163
post #156
post #150

Earlier quoted context omitted.

As someone who does systems engineering, the only valid requirements include the word "shall".

In a completely different field, navigating ships at sea, the Collision Regulations which define how people must conduct ships at sea, they use the words "Shall" and "May" to differentiate legal requirements and what may just be best practice. "Should" intuitively means something more like "May" to me

Happily, the meanings in RFCs are clearly specified, see https://www.rfc-editor.org/rfc/rfc2119.

Note "the full implications must be understood and carefully weighed before choosing a different course". Gmail and the other big hosters have full-time spam teams who spend a lot of time weighing implications, so I assume the implications of this was weighed.

Re: Major European payment processor can't send email to Google Workspace users

#164
post #149

Earlier quoted context omitted.

My take, as a postmaster for hosting company, who don't have any sympathy to gmail (that should be visible from my comments history): Message-ID is absolutely MUST in production e-mails. You can send your test stuff without it, but real messages always have it. Not having Message-ID's causes lot of fun things. All somewhat competent software is capable to add Message-ID's, so lack of it is good indication of poorly m…

Why? If I'm writing a mail receiver, and I'm told there is some unique ID generated by the sender in a loosely specified way , the first thing I'm doing is ignoring that value forever . One lesson surely most everyone learns in CS is that unique identifiers are maybe unique to the system generating them , but to rely on foreign generated IDs being unique globally is a terrible idea that will break within the minute.…

MID-s are used by MUA-s for referring earlier messages, tracking answers and so on. So any software expecting dialog (messages coming back) needs to deal with MID-s correctly. Missing MID-s show that said communication is one direction, because broken dialog has not been problem.

Re: Major European payment processor can't send email to Google Workspace users

#165
post #61

Worked on an ESP. We had a couple of server software we used on low-level for sending. None of them would accept the message without a Message-ID. But even if you have a super-custom, SMTP-injecting service built, how can you ignore all of these bounces from a provider thats likeliest to be the major one you are sending to? Unthinkable. I would not like to have business with such a payment provider.

I doubt Google Workspace is going to be the major provider for European businesses

...and you'd be wrong.

Re: Major European payment processor can't send email to Google Workspace users

#166
I offered to host a friends business email on my DO instance. Works 99% of the time but every now and then emails just disappear only to find out that MS and Apple block DO IP addresses, sometimes. Silently. There is a war on small email providers it seems.

Re: Major European payment processor can't send email to Google Workspace users

#167

Earlier quoted context omitted.

Worth mentioning is that there are several email umbrellas under Microsoft... including the newer office/365, the slightly older outlook.com hosting, the old corp hosting and hotmail and sub-properties... each with different rules and services to determine spam in inconsistent ways between them. One of my main emails is still on a "free" outlook.com hosted with a personal domain that I never shifted to paid 365. I've…

This issue didn't seem to discriminate. I was seeing deliverability failures to Office 365 clients as well as consumer-facing brands like hotmail and msn

Okay... I was just adding my own experience as I was able to deliver to some without issue and not the one. It's entirely possible this has changed in the past couple years since I was actively testing.

Re: Major European payment processor can't send email to Google Workspace users

#168
post #149

Earlier quoted context omitted.

My take, as a postmaster for hosting company, who don't have any sympathy to gmail (that should be visible from my comments history): Message-ID is absolutely MUST in production e-mails. You can send your test stuff without it, but real messages always have it. Not having Message-ID's causes lot of fun things. All somewhat competent software is capable to add Message-ID's, so lack of it is good indication of poorly m…

Why? If I'm writing a mail receiver, and I'm told there is some unique ID generated by the sender in a loosely specified way , the first thing I'm doing is ignoring that value forever . One lesson surely most everyone learns in CS is that unique identifiers are maybe unique to the system generating them , but to rely on foreign generated IDs being unique globally is a terrible idea that will break within the minute.…

>Why? If I'm writing a mail receiver, and I'm told there is some unique ID generated by the sender in a loosely specified way, the first thing I'm doing is ignoring that value forever. [...] So at that point the ID has no value to me

Your framework of analysis is based on someone else's database key ids being irrelevant to you. That's true.

But another framework of analysis is tracking statistical correlations of what spam looks like. Lots of spam often don't have message ids. Therefore it's used as a heuristic in scoring it as potential spam. That's why other postmasters even without SpamAssassin independently arrive at the same answer of trying to block messages without a message id. Example: https://serverfault.com/questions/629923/blocking-messages-w...

Re: Major European payment processor can't send email to Google Workspace users

#169

> Viva.com's outgoing verification emails lack a Message-ID header, a requirement that has been part of the Internet Message Format specification (RFC 5322) since 2008 > ... > `Message-ID` is one of the most basic required headers in email. Section 3.6. of the RFC in question ( https://www.rfc-editor.org/rfc/rfc5322.html ) says: +----------------+--------+------------+----------------------------+ | Field | Min | Max…

As indicated in the RFC, it uses another RFC[0] to define those words. Here's the relevant excerpt from that one:

    3. SHOULD   This word, or the adjective "RECOMMENDED", mean that there
                may exist valid reasons in particular circumstances to ignore a
                particular item, but the full implications must be understood and
                carefully weighed before choosing a different course.
[0] https://www.rfc-editor.org/rfc/rfc2119

Re: Major European payment processor can't send email to Google Workspace users

#170

I offered to host a friends business email on my DO instance. Works 99% of the time but every now and then emails just disappear only to find out that MS and Apple block DO IP addresses, sometimes. Silently. There is a war on small email providers it seems.

The biggest war on small providers is waged by other small providers. They can be ancient and outdated or simply extremely picky. Which makes everything Google or others require a piece of cake, which it actually kinda is.
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