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Have you ever tried configuring your own mail server? It's very close to black magic at times. Installing a mail server is easy, but configuring it to actually get mail into inboxes and not spam filtered or even blacklisted is complex. You could certainly do it yourself and supplement it with a galaxy of addons like you mentioned, but why bother when Sendgrid does all of it, through a simple smtp interface, and for pennies?

I used to configure my own mail server for scribophile.com. It took weeks to get it in a state I felt was acceptable, and even then it was through copy and paste without me truly understanding what was going on. When I had to move servers I said fuck it and went with Sendgrid, and I'm so glad I did! Instead of messing with DNS and domain keys and bounces and spam reports and user deliverability preferences I just dump a message to their smtp server and forget about it.

I have indeed configured my mail server. Maybe it's my bad choice in server software (Exim), but setting it up (also for receiving messages and exposing them using IMAP) was really not hard[1]

The Exim that comes per default in Ubuntu server has a default configuration that works as an SMTP server for a web application - no tweaks needed.

As I said: Your SMTP server needs two things:

1) You need an IP address in good standing. If you don't have that (if you are on EC2), you might need to sign up for an SMTP service (or sendgrid, but my concerns of using a nonstandard JSON API over the SMTP standard still stand).

2) If you have an IP address in good standing, you need a valid PTR record. You probably can't do that for yourself (unless you have an octet on your own or your provider goes really great lenghts), but all providers I have dealt with set this up for you no questions asked and without charging extra.

Then, getting the mail through through spam filters closer to the users is another problem, but Sendgrid wouldn't help you there either as this is largely dependent on the content of the email (and maybe a header or two like Message-ID).

1) http://www.pilif.ch/mail.txt is documenting the configuration. It's based on a newsgroup posting in 2001 - and it's in German.

Later on, Oliver Siegmar took my configuration and built http://www.xams.org/pages/home/home.php

This configuration plus the PTR record have lead to a configuration that is sending out 10000s of messages per day and we never had a blacklisting or spam filtering incident.

> 1) You need an IP address in good standing. If you don't have that (if you are on EC2), you might need to sign up for an SMTP service (or sendgrid, but my concerns of using a nonstandard JSON API over the SMTP standard still stand).

You only need the JSON API header if you want to use their "apps". If all you want is to send simple emails you can just use their SMTP server as a real SMTP server.

In addition to this, once I get a mail server running, I'm terrified to make changes lest incoming mail end up in a black hole. One time when I made an incorrect change, the backup mail server that godaddy "helpfully" put in my DNS settings started bouncing everything coming in. Even in the absence of a broken backup server, my experience has been that errors in the process are too frequent and take too long (on the order of minutes) to discover.

How true. Very recently I tried to setup SMTP for intranet and gave up 2 days after. There is just no simple enough guides. Most of them make assumptions of my knowledge, when I had 0 of DNS/SMTP servers.

Managing your own email server can be quite a task. If you're sending millions of emails per day you probably need a dedicated team just for this.

Some companies will prefer to outsource the sending of commercial emails and to keep the transactional emails in house. This is exactly what my employer is doing.

We're currently evaluating SendGrid as provider and I'm quite impressed with their services. If you don't want all the vendor locking then you can just use the SMTP server. You don't need to worry about any configuration, they will manage your server and all you have to do is to send plain emails.

If you want more services and are not afraid of vendor lockin then you can simple enable their "apps" and you get link tracking, event notifications, google analytics support, open tracking, etc.

Of course there are people that can handle setting up and maintaining high volume mail servers with analytics, etc themselves, and have the time and resources to do it. If a capable sysadmin is outsourcing sysadmin duties... well that just doesn't make sense.

I could probably figure out how to rebuild a transmission, and I've even got the tools and an engine hoist to do it, but it's not exactly high on my list of things to do and I'd rather take it to my friend that does it for a living so I can focus on driving the car.

I've spent many hours screwing with Exim on ded server I was using to do shared hosting. Every few weeks I had to worry about open relays and spam blacklists. I know if I spent more time I could learn how to stop those, but I would rather spend my time coding instead of admin'ing a mail server.