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Self hosting the infrastructure is incredibly easy. There are a lot of products out there that make hosting your own email system a cinch. One I'd personally recommend would be Cloudron, but I've heard MailCow is very easy, and I'm sure there are many other tools out there that sort of just 'do it for you'. Email deliverability on the other hand is... I'm going to say, it's not hard, but not easy either. Mainly you have to deal with blacklists, as well as certain providers being a bit weird. Staying off of blacklists can be both easy and hard. Most blacklist providers have several different layers of "Don't accept email from this server". The highest layer is easy to stay off of - just don't send spam. The layers below it might not be though. In particular, if your IP address is even in the same range as where other people might be sending spam, your going to end up on a blacklist because of it. So certain blacklists might have a 'Level 2' or 'Level 1' where if you use the same VPS provider as a spammer, your VPS that's never sent spam is going to get some of that 'bad reputation'. Email servers deal with blacklists in different ways - some just accept most things, some are a lot more strict. Usually email server will count up indicators for spam, and score them, and then, if it's above a certain score, the email bounces. Usually having a little 'bad reputation' (like from Level 2 / Level 1 like I listed above) won't be enough 'score' to effect things, but having a lot of it certainly will. I had an email server hosted on a VPS with a Level 2 warning, and my Gmail still got my emails. But I don't know if my emails would go well to all email providers (didn't do enough testing). In addition, some email providers will silently fail your emails if they don't pass - Google is pretty notorious about doing this. So it can be a bit of a pain to debug problems. The advantage of SES is that they deal with the reputation problem. They will jump on a Level 1 for a few days, then stay off of it for the rest of the month, then jump back on it again, and the cycle repeats. This is for the generic shared IP form of SES, so it's pretty good. It's certainly going to be more expensive, but you will need to send a good amount of email before it make sense to start managing reputation on your own probably. If you want the best of both worlds (although this sounds like what you are already doing), I'd suggest hosting your own server, but then using Amazon SES as the outbound email relay. Amazon's outbound costs are very very cheap, and that's what you need the reputation for anyways. It would be really nice if there was a system with fallback relays though, I agree. Let's hope that happens sometime :). |
The only thing I'm actually interested in is sending transactional email. I actually think paying a managed provider for it is the most pragmatic approach, but it seems like the existing providers are all pushing the limits of charging what the market will bear and, based purely on subjective info I've seen online, the margins aren't even close to anything resembling fair value (for me).
If there wasn't so much business and technical complexity related to bringing your own IPs, the $10k ish (?) it costs to buy a /24 starts to look like a reasonable expense when put alongside the pricing of a lot of email sending services.