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

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.

> 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.

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.

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.

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).