How do you send transactional emails?

Outlook.com blocked my transactional emails sent via sendgrid.com. From what I learned, outlook.com used a simple per IP reputation system. Since I am on a cheap shared IP plan of Sendgrid, and there must be someone sending dubious email with sendgrid, therefore, the situation is hopeless.

Outlook.com also blocked IPs from major cheap hosting companies. The good thing is that if you file a complain with them and show them proof that you do own the IP, then they will unblock it on a case by case basis.

How do you guys send transactional emails, and what are your experiences? So far I’ve tried to avoid SES, or anything from AWS.

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I’ve used Postmark to good success previously (https://postmarkapp.com/), and would definitely use them again. And I had the same problem with Sendgrid that you encountered.

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SendGrid gradually deteriorated in the last few years. Seems everyone is migrating to PostMark lately, including people on HN.

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Amazon SES because I’m cheap. But I heard very good things about postmark so might switch to them at some point.

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I’ve used Sendgrid, SES, Postmark, and Mailgun. I like Postmark a lot, but tend to use Mailgun for most projects because it’s very cheap at the outset when you’re not sending many emails and it has all the features I need (mostly around seeing what was actually sent to recipients). I tend to think anything without a dedicated IP is prone to trouble, but haven’t had trouble with either of Postmark or Mailgun.

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I don’t think it is SendGrid’s fault. The big email providers are basically holding the mass in hostage, and the war on SPAM has gone way over board. If I move to postmark what guarantee do I have?

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What I have found is if you use a competitively priced VPS vendor and do your own sending, it is even more troublesome. outlook at least has a channel to complain; mail.qq.com only pretend to have one and no one would get back to you and your IP stays blocked forever.

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Not sure if any of these are any help:

https://sendersupport.olc.protection.outlook.com/snds/FAQ.aspx

https://postmaster.live.com/pm/troubleshooting.aspx#errors

We’ve had issues with them when moving to new servers/ips in the past (though not recently). Usually once you reach out to them it gets fixed… but I imagine that would be harder for a shared IP service.

If you can install your own software on the server/host perhaps look at Dovecot and Postfix…

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Thanks, this is exactly what I did. Then I have delieverability problem to a different set of hosts :frowning:

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Make sure you have a valid SPF record. Sometimes they include troubleshooting info to let you know why your mail can’t be delivered too - are they giving you any indication?

I would also contact sendgrid… if you are paying them for email and it’s not being delivered it’s not really fit for purpose :upside_down_face:

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One of the things I like about Mailgun is the setup for SPF and DKIM has clear instructions. I like the directive to place records on a separate mg subdomain rather than tacking on to the SPF record for the root domain, which I’ve previously seen get overloaded (there is a limit) and messy.

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Trust me, I’ve done everything. Life is not fair if you want to send transactional emails with a very limited budget to people beholden to the monopolies.

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Don’t give up… sometimes it can take them a while to sort it out.

You could also enlist the help of your users… ask them to contact the support dept of their email provider and ask why their emails are being ‘censored’! We’ve had to do this on a few occasions in the past! :lol:

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Highly recommend Postmark. They only do email and they do it very well. Excellent dashboard that lets you get answers when you’re under a time crunch. Used others in the past but Postmark is by far the nicest.

Also, they guide you through getting it properly set up with DKIM and Return-Path. Removed a lot of the guesswork for me. Working at a startup I’m juggling a million things at once and Postmark just brought me joy and respite – not more problems.

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Sure, I agree it’s an arms race but what recourse do we have? We best just migrate to the service du jour that works today. Not like I disagree with you, I am simply being pragmatic.

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At work, we’ve decided to use a dedicated IP on SendGrid to avoid the same situation you described.

If you decide to go this way, you would have to authenticate your domain.

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Sorry, to clarify, I meant a dedicated IP on one of the services rather than hosting your own. It sounded like that was not what you were looking for from a budgeting standpoint though.

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This isn’t a solution for your SendGrid problem, just an anecdote.

When SES shut us down a few years back without explanation, appeal, or recourse, I moved over to Sparkpost which has been reliable for the last several years.

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I’ll put another vote behind Postmark. They have been great for me (though my usage was on the smaller side).

I’ve even contributed to the Elixir Swoosh library to help integrate Postmark’s broadcast email services:

I’d also recommend their resources as a general source for great info on email things regardless of provider.

Good luck!

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I have an app that needs to send an occasional transactional email and also sends a newsletter for parents of school kids. Postmark docs were really useful for doing a proper setup (have two domains for transactional and non-transactional emails). I really enjoy their service and I feel like I’m getting my money’s worth.

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