Ask HN: What to do when Google is about to kill your business?

[oscgam1]

We are having an issue with Google. All of our email is going to spam (including email between team members).

We have a Domain reputation of 100% as per Google's own tool (Postmaster), and we are following all of Google's best practices -> SPF is set correctly, DKIM, DMARC, the emails are only sent when the customer selects to receive an email, and we include a visible unsubscribe link.

Our whole business is paralyzed, and Google customer support doesn't seem able to identify the issue. It has been 2 weeks.

Is there something else we should be doing?

[AussieWog93]

>the emails are only sent when the customer selects to receive an email, and we include a visible unsubscribe link.

Just for what it's worth, sometimes when a company's marketing is really obnoxious I'll mark it as spam just to fuck with them.

If there are enough people doing that, one could imagine that Google's internal filters would begin seeing the whole domain, or some random boilerplate string in the emails as an indicator of spam.

Have you started manually flagging messages as "not spam" on mass?

[sam0x17]

> Just for what it's worth, sometimes when a company's marketing is really obnoxious I'll mark it as spam just to fuck with them.

I do this for _all_ marketing emails. Report + unsubscribe every single one, unless it's a mailing list I signed up for which I would never do willingly.

I don't know why startups think they can send unsolicited emails or force people into a mailing list and get away with it in 2023.

[oscgam1]

Thanks for the reply.

I Agree that marketing email are super obnoxious. In the very few instances that we send (e.g. black Friday), we include an unsubscribe link :)

Yes, we are informing our customers to flag us as not spam. However, our domain reputation is 100% (google's postmaster) according to Google's support, this doesn't seem to be the case.

We will continue informing our customers and helping them set filters so they can receive our emails (eg. forgot password and other important emails). But everything on Google's side is showing as OK and we are still left without an answer.

[esperent]

Do you send unsolicited mail that customers didn't specifically sign up for?

I get so much of this, I sign up for a service to check it out, decide it's not actually a good fit for me but in the process of signing up the company added my email to loads of mailing lists like product updates, advertising, policy changes, etc. etc.

The company doesn't see this as spam. However, it is spam and whenever I receive any of this mail, whether there's a (legally required) unsubscribe link or not, I always mark it as spam.

Don't send email to people unless they specifically ask you to send it. Mailing lists must be opt-in, not opt-out. Otherwise they are spam.

If this is why your mails are being flagged as spam then I agree with Google here. If it's another reason then you have my sympathy.

[oscgam1]

>Do you send unsolicited mail that customers didn't specifically sign up for? No

I agree mails should be opt in (we do it that way). We send some transactional emails such as forget password, purchase receipts, and welcome email.

We already had a good domain reputation, that's why the situation is so difficult to fix.

[jfoster]

Do users have to verify their email address to get onto your lists?

I get mail from lots of real businesses, but I never engaged with them, so they're marked as spam.

[farseer]

I do this too, especially those who tricked me into signing me up using a dark pattern

[jerryu]

Change the domain to use for email marketing only. Redirect it to main website. Just use it to send/sign mail.

[svillar]

If all else fails and you want potentially better customer support, I would give SendGrid a try. I have had very good results with them. In a similar case, someone from their tech support spent over an hour on the phone helping us sort the issue out. And it was a mix of things, configuration, etc

[sli]

> ..., and Google customer support doesn't seem able to identify the issue.

This cannot be anything but a lie, right? I refuse to believe that there's no way they can't just view some sample emails and approve it manually if it's all above board. I definitely believe they simply do not care. But unable? No way.

[is_true]

It's likely true. When you commoditize people you cannot trust them, so the support crew probably can't do anything.

I've seen it first hand with fake Google My Business reviews, the support person told me it knew those reviews were fake but it couldn't do anything.

[than3]

I agree, the support crew often is just part of a support loop of doom. No escalation paths.

You have to have connections on twitter or reach out to corporate after failing to resolve the issue. Its designed to eat up your time while providing no resolution.

You have to be big enough to get any kind of attention from someone that doesn't want to see egg on face in the news, but in general for email, this is not much of a concern.

[hansvm]

Check the outbound IP of the physical machines sending the mail, and any other potential identifiers in the raw email which might have poor or zero reputation from other parties. You aren't graded just based on the official crypto signatures.

Also, did that domain ever send shitty emails? Opt-out marketing is the most common offense I've seen from otherwise above-the-board businesses (no matter how justified you think you are or how great your product is, no rando wants to hear from you, and your paying customers definitely will be pissed off that they paid good money and still have to filter out marketing for the privilege of using your project -- you'll definitely end up in the spam bin).

[nickphx]

Have you checked your domain against common blacklists? https://mxtoolbox.com/blacklists.aspx may be helpful.

[kazinator]

Not just the domain, but the IP addresses of the machines that deliver mail on your behalf.

[jasfi]

Use an additional email testing tool, e.g. MailTester: https://www.mail-tester.com/

There are others too, many have a free quota that you can use a few times a day. With MailTester you can retest the same email after changing things as well.

Perhaps Postmaster missed something.

[mesozoic]

Random idea try different service or server IPs to send from. Could be you send from the same server as a spammer?

[dossy]

Send me an email at REDACTED, let me take a look. I can probably give you a few deliverability tips, if you want.

When you've sent it, add a comment here so I know to look at my mailserver logs in case my mail filter hard rejects the mail.

[oscgam1]

Thank you, email sent.

[birdyrooster]

Send me an email at REDACTED too

[kazinator]

> Is there something else we should be doing?

Trying different SMTP providers, probably.

Your mail domain is something that appears in the From: header of your e-mails.

However, mails can be rejected as spam even without any of the headers or body of the e-mail being seen, at the SMTP level, and that could have to do with who you route your mail through, or who your sending or forwarding mail servers are co-located with in the same IP block. IP addresses which have nothing to do with each other can tarnish each other's e-mail sending "reputation".

[pomatic]

Isn't the obvious fix to change suppliers? Google does not have a monopoly on your domain. A quick search through historical hacker news articles will turn up dozens of tried and tested alternatives to Workspaces. (e.g. Fastmail)

[oscgam1]

Hi, thanks for the response.

The issue is not about sending email (switching providers). The issue is about our customers being able to receive the emails. If we send email to other email clients, they receive the message.

The issue occurs when our customer uses Gmail or any google product. The mail gets classified as spam in those cases.

A good guess is that Google/Gmail maintains their own internal private blocklists, and our domain is most likely on it (even if it is a false positive).

[pcdoodle]

We've have the same issues, a customer emails us from a gmail account and we can't email back. Never spammed anyone.

GMail is not email.

[KomoD]

What are you on about?

[verdverm]

Contact support, I cannot think of a reason email between team members using the gmail domain should all be going to spam.

[dutchbrit]

Try using SendGrid or Mailgun.

[than3]

Unfortunately, this is just par for the course.

Running professional email servers in business is an ongoing exercise in extreme risk management. There are so many moving parts if you don't have systems in place you end up getting fallout like this, and it changes all the time without notice or disclosure. Often at best its a guess, because these large providers do not tell you why, nor provide support when their feedback systems say nothing is wrong. Technically, its an FTC violation, for deceptive practices, but they haven't had any enforcement in years thanks to our congressional representatives taking a yearly salary of 200K+ and not doing hardly any effective work.

But I digress, You should have had your marketing segmented to a different domain from your transactional emails. Ideally a completely different server, but a subdomain works in the short-term.

This will likely be the quickest way to get things back up and running. Create a subdomain just for transactional, and start warming it up, slowly, (i.e. send mail to an account you can check, open the mail, they record these clicks for metrics, increase the volume gradually, make sure you have rate limiting; per day and per hour, by recipient base domain). Ensure there are no mis-configurations by checking with a service like Mail-Tester. Then start pruning your email list for people that do not respond an affirmative after a set time. Ideally you should be sending them at least one email every few months to confirm they still want to be receiving emails. Any non-response should drop them from marketing.

Additionally Google and many other large ESPs fight spam by testing against whether you are in compliance with the workgroup whitepapers that are regularly published. There are a lot of them, and they also weight you worse if you have drastic changes in volume.

The whitepapers can be found at M3AAWG.org.

One of the most difficult to diagnose issues from a senders perspective are spam traps. Google will automatically mark as spam internally if you send to one.

Not only that, mis-configurations can get you flagged regardless of what you do, for example like not having a correct PTR record (reverse dns lookup) because your ISP changed it without telling you.

Yes I've seen this happen at some local ISPs, and most of the people I had to go through to get that fixed were completely incompetent with no guarantees they wouldn't do it again. In those cases with little choice for ISPs, there isn't much of a choice but to set up a load balancer to run everything through in a data center that does provide that level of guarantee. Cheap data centers plans or services won't, and may block those ports. Colocation usually is more expensive, but if they touch your equipment there is legal remedy.

A spam trap is some email address that has been disabled for a month (rejecting email), and then turned back on. If this is your problem you are not properly managing your subscriber lists.

You may also be penalized more if your mail being sent by your server is not including both TXT and HTML (having just one is often considered a mis-configuration), or does not support list-unsubscribe.