Hosting your own email service is way more difficult than just spinning up a smtp server and some interface. Most big providers (like gmail) are more likely to flag incoming mails from unknown servers.

That's the reason why stuff like Sendy[1] is so popular. You host your own interface, settings and so on, but the ugly part of sending your email is handled by AWS SES.

[1] https://sendy.co/

That's only true if you're spamming people a lot. Running your own postfix server is trivial, and you'll have a fine reputation so long as you aren't sending marketing BS.

Unfortunately, this is the total opposite of my experience. I've never sent any spam from my domains and yet Gmail refused constantly to let any of my emails through regardless of my VPS provider, my DKIM/SPF setup and so on. The _only_ way I could solve it is by letting my email be managed by some other email service provider (I went with Zoho but I don't think it matters).

Running own SMTP server for personal use is hard. Google is the worst adversary just because of their market share.

I have a mail server for personal use, and I send less than 10 mails per day for many years. DKIM, SPF, DMARC are all properly set up. I am signed up to all possible postmaster tools, including that of Google.

Still, Google started blocking mail sent from my IPv6 address in December. I switched to IPv4, and it fixed the issues for existing gmail recipients, but new recipients usually see my mail in Spam. When I don't get a reply for a few days, I mail them from my backup @gmail.com account and ask to unmark me as spam and add to contacts. So far, this helps.

P.S. I also run a community website on a different domain and IP. It sends tens of thousands of notification emails per month, and it fares better in Google Postmaster Tools. User-reported spam is within 1% and it seems that this is acceptable behaviour for Google.

My current impression is that Gmail is sort of broken in general. There isn't really anything you can do to insure that an email will get delivered to Gmail with 100% certainty.

Presumably people who actually care would not be on a free email service in the first place...

> DKIM, SPF, DMARC are all properly set up.

Does the IPv6 address have matching forward/reverse DNS?

Yes

This isn't true. When running my own server Google will send me emails but will not allow me send emails to my Gmail account. I know it is configured properly because I can email other services just fine.

I found many servers will block you if you first send them email (e.g. greylisting). If you can get them to send you an email first, then everything tends to work from then on.

Kinda two use cases here with my being more on the business side than personal, that's true. You may be right for small personal scenarios.

probably depends on the amount of mails you send. i have done this with thousands of emails from a dedicated server and they didn't end up in spam

Sadly, Google will flag as spam most new email servers by default. Email deliverability is a cartel these days.

yeah, came here to ask -- how do you not end up in the gmail spam folder?

I'm surprised that someone is having problem sending email to gmail from their own smtp server. I am doing this for years with tens of thousands emails delivered every week (sometimes daily), yet had no issues. Here are few advises:

- ensure your external IP reputation is good. Check blacklists.

- configure correct dns/reverse dns (PTR) records.

- setup SPF (maybe DKIM with DMARC but I'm not using these)

- do not spam.

Thats it.

If only it were that easy! This usually isn’t enough anymore.

First off, you don’t really have control over your external IP reputation, unless you have your own IP space, which most people don’t.

You’re at the mercy of your colo/hosting, really. You get whatever IP they give you, baggage included. I think the reputation is also subnet-based, not IP based, so your potential to be included in someone else’s blast radius is increased.

Also, even with a clean IP, the steps you outlined are not sufficient to send significant numbers of non-spam messages and not get spamboxed. Gmail seems to be mostly okay with erring on the side of false positives.

Source: been running my own email servers for 25 years

then how do the email services , who post massive amounts of emails and many of them are spam manage to get through? do they have some kind of deliverability deals with gmail?

(btw my mails also seem to get through and i haven't even set up DKIM)

Short story, yes, they do.

Plenty of people report that there is a minimum amount of email you have to send so that you can contact gmail and ask them to unlock you. They, of course have a set of rules you have to follow.

But you won't get them to receive your email if you just send some 3 messages a week.

One reason is that the services are actually quite cheap if you are running a real business. Likely better to spend time on your core thing instead of tinkering with mail server.