So, I've run simple Postfix + Django emails for transaction confirmations, password resets, and in …

I run a site for a large corporate client. People can sign up to get a quote from a regional dealer for a specific type of complex product. To get a quote, they have to fill out several forms, and select detailed specification, etc, and choose email as the way to deliver the quote. We regularly have users flag the email they receive from this process as spam. I have personally called to follow up in some cases to understand if our service was being abused or what the issue was. It was eye-opening. One user said "oh, yeah, I wanted that when I filled out the form but not when I got the email." Several marked the proposal as spam because they didn't like the final quote that was put together from their requirements. Several said things like "I get too much email" and when pressed as to why they checked the box that said they wanted their quote delivered as an email replied that they didn't…

I run an email domain for myself and three friends. I set it up 10+ years ago and originally it was for ~15 people. It's only personal email and no one uses it for marketing or anything even remotely shady. We setup DKIM and all of the similar best practices. In the last 6-12 months, we've had lots of issues with gmail marking our messages as spam for users we haven't emailed before. And what sucks about it is there's nothing you can do. People assume it's your fault for being weird and not using Gmail or outlook.com. And there's zero way to contact Google or submit information to convince them you're legitimate. I believe in an open, distributed internet. I don't think it's good that we're moving towards a world we're the core protocols that defined the internet are being replaced by proprietary versions controlled by a handful of trillion dollar companies.

You can be judged for your entire IP range if you use the wrong VPS. DigitalOcean is one such place. They put all their domains on spamhaus by default, which you can get removed, but it seems MicroSoft and some others still don't like you just for being from DigitalOcean. I never sent any spam from my IP that I had for a decade but ran into this when I tried delivering to MS emails even after getting removed from spamhaus. Setting up a gmail relay that retained my from: address did the trick though.

> we did double confirmation "Double confirmation" is spammer-speak. The correct formulation is "confirmed opt-in".