Twilicorn

Postal is my favorite: https://postal.atech.media/

AWS has a vested interest in upselling you SES for email-sending needs. The quality of their EC2 IP ranges has little to do with their size; running a tighter ship with those IP's is merely bad for their business model.

Deal with the spam feedback loops - they exist for a reason. You have to treat an FBL email as someone hitting the "unsubscribe" link (though it might also be an indication your unsubscribe link has to be more visible or your unsubscribe process less obtuse). Some off-the-shelf software can monitor your bounce and FBL messages and automatically process them as such.

Getting blacklisted is a temporary state and I maintain it's easy to recover from if your IP's and domains had a good history. I've experienced the IP's that email hosting services send my mail through being blacklisted and then waiting days for them to deal with it versus being able to contact blacklists on my own behalf to resolve things same-day.

I used to pay one of these services $xxx/month and experienced delivery rates around 60-70% that they couldn't do anything about other than offering me a dedicated IP for a lot more money. Moved to my own mail server with an OSS transactional email system and delivery rates shot up to 99%-ish while eliminating the email bill.

One anecdote against another. My suspicion is that you were in a "bad neighbourhood" - ie. using a hosting or email service that didn't keep their IP's squeaky clean. AWS/EC2 is a common host among the HN crowd but is one of the worse places to host a own mail server at for this reason - they'd also rather upsell you SES than fix the EC2 IP ranges' reputation.

Microsoft is the pickiest email provider to get good delivery rates to - they require a gradual volume ramp-up over 1-4 weeks on a fresh IP to see it as good, in my experience, and SNDS is something to keep a close eye on during that time - it clearly indicates your IP's reputation with them and how much mail they see from it. That number being higher than expected plus the sample emails they provide may indicate something going wrong - through this, I once discovered an obscure feature in a software package I used that allowed visitors to send emails to arbitrary addresses.

Mandrill has better delivery than the other email services I've tried but is cripplingly expensive for a hobby project that happens to have a nontrivial userbase.

It doesn't even take months. Reputable hosting companies give you a "clean" IP that isn't on any blacklists; its reputation is yours to make or break from that point onward. Send clean mail from the get-go and the IP's reputation goes from "neutral" to "trusted" very quickly, in a week or two tops.

You end up on blacklists by sending out spam. Don't spam - meaning, don't send unsolicited emails. That's it. That's all. Done. There's no magical secret sauce to this like SES, SendGrid, Sparkpost, and friends want you to believe.

There are two things you have to do to not spam:

- Don't be the one sending spam. Don't send your users any email they don't ask for short of extenuating circumstances that truly or legally warrant it, like a security breach. Just don't. This also includes making it brain-dead simple to unsubscribe from anything they once signed up for.

- Don't let anyone else send spam through your server. Keep it locked down. Lots of criminals are constantly prowling the IPv4 address space for poorly secured mail servers to fire out a million crappy scam mails from before a blacklist notices.

The amount of work that blacklists create is grossly overblown. If you're doing email right, the only time you'll ever interact with one is when your mail server gets owned - in which case, you send the blacklists a quick note to explain what happened, that you fixed it, and they take you off of it within a day.

Sign up for mxtoolbox.com, secure your server, respect your users' inboxes, and you only have the box's uptime to worry about.

I have a counterexample for you. Start an Internet forum as a side project that lets users subscribe to threads for email notifications. Grow it to xx,xxx users making x,xxx posts per day.

Before you know it, you're sending 20k-50k notification emails every day, and over a million emails a month, without making any money or while barely staying afloat with $100-400/month in ad and donations revenue.

Almost none of the SaaS or IaaS solutions HN loves to praise are within this use case's price range but scrappy not-for-profit communities like this deserve to exist, too. You're basically limited to leasing a bare-metal server or two and making it do almost everything you need.

The difference between $100/mo and $900/mo is the difference between getting to stay online or shutting the forum down. Even the difference between $10/month and $100/month might be enough to close shop over.

Personally, in this scenario, I've found setting up my own mail server with a tool like Postal or Cuttlefish to be worth every minute and delivery rates to even be better (due to getting to manage my own IP address's reputation vs sharing a mail-sending IP with anyone else).