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Ask HN: The middle ground for email self-hosting?

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Re: Ask HN: The middle ground for email self-hosting?

#51

Post by outsomnia »

raegis wrote: post #36
outsomnia wrote: post #11

Incoming email is simple, MTAs have no problem at all delivering to residential IPs if that's what your MX says. So ideally you should run your own postfix + dovecot at your premises and point your MX to that. You have to take additional steps for sending email. > would my custom domain be free from being marked by spam? The receipient's mail service gets to choose if it thinks your email is spam, this will happen wh…

I think $30 a month is high just for email. I do $5/month now and have been doing this for over 20 years on my domain. (It was more expensive in the past.)

Yes, you can do it on a VPS much cheaper.

But this is your outgoing email authorized by DKIM... an attacker can use it to take over most of your accounts via Forgot Password flow. I think it is a false economy to have that depend on a shared VM.

Re: Ask HN: The middle ground for email self-hosting?

#52

Post by dugite-code »

dmje wrote: post #18

I just don't understand the attraction of self hosting email. The pain seems extreme, even for those who understand the considerable number of nuances. To me the happy middle ground is email on your own domain but using an existing provider such as G / MS or whoever. That way you've got control but don't need to worry about the pain. It does require paying for but really on balance not much. If you're spending more t…

I've selfhosted my own email for almost a decade now. I was spending about 5 min a month on it until my ip block rep died one day for little decernable reason. Then I wasted many hours on it so I switched to sending through amazon ses and I'm back to my 5 min a month (updating packages/checking logs).

It has a few advantages because I can run a bunch of automations and filters. Honestly I get less spam than in my gmail inbox, so I harvest spam from gmail to train my filters now. It's insane to me how much providers charge for an inbox and the tiny sizes many still offer

Re: Ask HN: The middle ground for email self-hosting?

#53

Post by defanor »

michaelt wrote: post #43
defanor wrote: post #35

A major theme in self-hosted email discussions is deliverability issues (particularly to larger email service providers), and I tend to be unsure how bad it actually is: sometimes it does seem pretty bad, other times it sounds like it's fine, and possibly the chatter about failed deliveries is caused by misconfigured servers and/or misunderstandings. Seems like it shouldn't be hard to check and collect reference stat…

The problem with deliverability issues is the impossibility of proving a negative. If I send an e-mail to a company's customer support, or to my senator, or I reply to a potential client, or I contact an open source mailing list and I don't receive a reply - do I know if my message made it to them or not? I mean, it's plausible that JohnDoe@senate.gov just didn't deign to reply to my e-mail. But it's equally plausibl…

Sure, strictly speaking it's impossible to ensure that a message was actually read by a user even with automated end-to-end delivery acknowledgements and/or in centralized systems: UIs manage to gobble/hide messages, users fail to find how to open attached documents (and declare that those are missing), etc. But I imagine that a survey/statistics would still help to estimate how bad deliverability in general (in a variety of common cases) is: without that there are differing and even more vague ideas of its state.

Re: Ask HN: The middle ground for email self-hosting?

#54

Post by noduerme »

pxeger1 wrote: post #22

I've done this with Amazon SES, which is PAYG and costs me pennies. https://www.pxeger.com/2020-07-02-hybrid-cloud-email-with-am... It is a bit overcomplicated, because I also set up SES to receive email, but I could run that instead with an ordinary Postfix server. It would be much simpler for outgoing only, I think

SES is good for loads of outbound mail.

People don't know this, I mean no one knows this, but if you're running an EC2 instance with some allocated IPs, you can contact Amazon's customer service and ask them to unthrottle outbound mail on it. Typically they clamp down and stop connecting any SMTP deliveries off the EC2s if you do more than 10 emails/hr or something. But if you plan on keeping the IPs for awhile you can set up DKIM and SPF and all that, call Amazon and tell them you're sending and receiving legitimate business emails off that server. They may try to refer you to SES, but if you tell them you need to manage it on a private server for legitimate reasons, they have the ability to lift the block for you.

Do check your allocated IPs for blacklisting in advance, and obviously don't give them any cause for being blacklisted in the future.

Re: Ask HN: The middle ground for email self-hosting?

#55

Post by rockwotj »

hannob wrote: post #32

You should be aware that Microsoft's SMTP servers parse the mime structure of the mails and restructure it in a non-standard way. I have no idea why, but for example this breaks PGP signatures.

This is due to a well known fact that Microsoft hates the email ecosystem.

I work on a email client and a large majority of "this email is broken" is due to weird outlook behavior. Most recently it's TNEF attachments: https://en.wikipedia.org/wiki/Transport_Neutral_Encapsulatio...

Re: Ask HN: The middle ground for email self-hosting?

#56

Post by cubesnooper »

outsomnia wrote: post #51
raegis wrote: post #36

Earlier quoted context omitted.

I think $30 a month is high just for email. I do $5/month now and have been doing this for over 20 years on my domain. (It was more expensive in the past.)

Yes, you can do it on a VPS much cheaper. But this is your outgoing email authorized by DKIM... an attacker can use it to take over most of your accounts via Forgot Password flow. I think it is a false economy to have that depend on a shared VM.

You don’t have to store your DKIM keys on the VPS. I keep my signing infrastructure local, and send outgoing mail over a WireGuard tunnel so it looks like it was sent from the VPS.

Re: Ask HN: The middle ground for email self-hosting?

#57

Post by nicbou »

josh_fyi wrote: post #23

I do outbound email for my domain from a generic Gmail account, where my domain address is added as an alternate "Send mail as". This gets sent through Mailgun's free SMTP. Incoming email to my domain is forwarded through Cloudflare's free service to the generic Gmail account. This seems to pass all quality checks to avoid being sent to spam.

I do this but with Namecheap + Gmail. It has worked flawlessly for years.

The only issue is that emails don't come in instantly. They can take up to 15 minutes. I consider this a feature, but it would be really annoying to some.

Re: Ask HN: The middle ground for email self-hosting?

#58

Post by Avamander »

hannob wrote: post #32

You should be aware that Microsoft's SMTP servers parse the mime structure of the mails and restructure it in a non-standard way. I have no idea why, but for example this breaks PGP signatures.

They break way more than that, it's quite annoying. If you search in various MTA/client mailing lists you'll find a bunch of threads.

Though, others do violate standards as well, but not like this.

Re: Ask HN: The middle ground for email self-hosting?

#59

Post by dspillett »

defanor wrote: post #35

A major theme in self-hosted email discussions is deliverability issues (particularly to larger email service providers), and I tend to be unsure how bad it actually is: sometimes it does seem pretty bad, other times it sounds like it's fine, and possibly the chatter about failed deliveries is caused by misconfigured servers and/or misunderstandings. Seems like it shouldn't be hard to check and collect reference stat…

> and I tend to be unsure how bad it actually is: sometimes it does seem pretty bad, other times it sounds like it's fine

That is pretty much it. One factor is that once you are on a blacklist it can spread like wildfire and be much faf to get off them all again, so the risk is small but the hassle if it happens is high. Also if you send mail for numerous people there is going to be a much higher risk: every extra user/account/address is an extra hack target (do all your users have good, non-shared, passwords?) or just extra volume that might be accidentally classified as junk (and once something from your server gets classed that way, future content may get more aggressively analysed and more mistakes may happen).

I've run my own mail server, including sending mail directly, for many years and to my knowledge not had a significant delivery problem. But I have a few mitigating factors: the IPv4 address is essentially on a commercial ISP range, not one that looks like a residential account or a VPS service provider, and the ISP is one that takes junk mail seriously, so there is less “splash damage” potential, and the same range has been used this way for several years (the main sender has moved around that small range, when testing upgrades on a copy VM for instance, but never away from it entirely) so it never looks like a brand new mail server these days, I only serve myself and a very small number of other users, our outgoing mail volume is pretty low.

It is a bigger problem for hosting services (much bigger user-base and little control over what they might send) or if you are sending from one of their ranges, if sending from a residential ISP address range, if your volume is high (perhaps you have apps that send mail as well as your personal mail?), etc., but it can be a problem for everyone.

I'm rebuilding my mail service soon (moving off Zimbra to just configuring the parts myself, as we don't need the extra features these days, it is too chunky for just a mail server, and at the end of next year they stop releasing easy install packages for the non-paid users (they already have for v9., next year v8. hits EOL)) at which point I might reconsider where it is hosted and if I should be sending via a paid SMTP relay to let them worry about deliverability, though as far as I know I've not had a problem.

Re: Ask HN: The middle ground for email self-hosting?

#60

Post by ulrikrasmussen »

Many VPS providers have an SMTP gateway that you can use to ensure that your email does not get marked as spam. I use transip.eu and never have problems. Prior to setting up my mail server to use their gateway, I ONLY had problems with Microsoft-based receivers such as @outlook.com. So please, don't use Microsoft for anything email related, as they are currently one of the worst offenders in making it hard for people to run their own mail server.
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