I've seen this with my SaaS. We ONLY send transactional emails like purchase receipts and login links (using postmark). We're very intentional about not sending anything remotely resembling marketing or spam, and sending as little as possible. Yet I still get the occasional user who will flag their purchase receipt as spam when all they really mean to do is delete it. They don't get the difference and don't realize that it matters which button they click.

I've noticed that in the past year or so gmail has made hitting the spam button more explicit and now have a confirmation message. Obviously they did this because some people were simply mashing that spam button instead of the delete or archive button.

I don't even blame the users. Most don't know the impact it has. But bad actors sending tons of spam have trained them to be cynical of any generic form email.

Google does put some senders often into spam for me, but not always. I'm absolutely sure I've never reported them as spam, on the contrary: I've marked their emails as "Not Spam" when I caught them in the spam folder.

That had, so far, no influence on the filter. Those aren't "weird" emails either, they are in my language and individual communication, not mass mails.

Maybe gmail shouldn't have the spam button right next to delete :)

At least that's better than web Outlook's invisible, until you click on the sender, microscopic disposition buttons. I can't count the number of times I've deleted an email instead of opening it.

I have a relatively high profile email address (first initial and last name) and I almost daily get at least one form of "receipt" from a transaction someone made where they entered my email by mistake.

Sometimes I'm in a bad mood and I'll mark anything I see like that as spam partly because its frustrating and partly because I suspect a good number of these emails actually are spam masquerading as receipt/login/etc emails.

And I just don't have the energy to figure out which are legit or not.

And yet other companies with spam reporting features are able to maintain a lower false positive rate with their spam filters.

I've considered adding an opt-out checkbox during checkout but I honestly doubt it would ever be unchecked and if it was opt-in we'd have users contacting support asking for it because they didn't realize they had to check the box. Either way it's one more toggle on the UI which I'm not a fan of unless absolutely necessary.

I'm curious if you've run a business and experimented with not sending receipts, and if so how it played out?

The purchase history on website disappears, logins get forgotten and so on. Only receipts in the mailbox stay forever, as I want them to.

Also, a lot of users do perceive receipts as spam.

My own server has a good reputation, but it meant setting up SPF, DKIM, DMARC etc.... Where it was the most painful was with microsoft email (I don't know the name of their service now, still live maybe). By default mails goes to spam, but really quickly they goes in limbo if people don't respond (on the smtp side the email is accepted but the recipient never see it, not even in spam). On new microsoft accounts I was always able to send a few emails in spam before it went into limbo. I ended up creating ~20 different accounts on their system (it was before they enforced giving a phone number) and had random discussions with myself for a while which was enough to build a reputation and not being put in spam anymore. I don't know if this behaviour was intended or not, I try to get in touch with someone from microsoft but couldn't find a way. Since then I do strongly advise not to use their system because that makes it really unreliable.

I’ve got everything setup properly, all test websites come up green, and google receives my email just fine. SPF, DMARK, DKIM, PTR, HELO are all setup correctly. This isn’t an isolated problem either, the ms forums are filled with people reporting similar problems.

Slightly tangential ... I heard recently that "proper" in-line responses (ie, not top-posting) is somehow penalized by Microsoft (or Exchange online or Outlook online or ... ?) and was advised to stop my very proper 1990s style in-line email quoting/responding and just top-post to avoid either non-delivery or something like the body of the email not being shown ...

Or something ?

Does anyone know what I am referring to and can shed some light here ?

But yeah, that's usually more an issue with the mail client (or perhaps the mail server if it's being exceptionally stupid and modifying emails before final delivery). Top-replies became the norm for some god-forsaken reason, and now clients treat the quote and everything below it as entirely optional to display.

I found an important email (from 3 days ago) from a recruiter asking for my CV in it.

Yeah, Google's spam has erred too far towards making false positive errors.

As another data point, for me and friends I it beats competitors by a large margin.

I guess it's another case of survival bias. If it works you won't notice that it does not work in all cases.

Anti-trust regulators should specifically look at situations where Google began directly competing with other companies and those other companies gmail messages are being put in spam while Google’s messages are not. Whether or not it is intentional, it is a problem if Google is whitelisting their own stuff but not competitors.

Ultimately what is going on here is Google is using more deep learning for spam detection. Your friend’s email ending up in spam may be a false positive. It may also be a test, to see if you notice it.

As a bonus, if you require opt in, I won't be able to cancel your car reservations with budget ROBERT.

I absolutely click spam on every single one of those pieces of mail, and I'm glad that they are being penalized for it.