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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?

#61
post #57

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.

> 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.

I have a somewhat similar setup, slightly different. Most emails arrive within 10-15 seconds, but sometimes gets stuck somewhere along the line (as it happens with emails), which is normally not a problem.

But some platforms force you to use the "send link to login via email" option for login, which again, normally is not a problem. But when they have a timeout of 10 minutes + it takes 15 minutes for it to arrive, you end up not being able to login.

Only happened to me a few times during the years of this setup, but when it does happen, it really sucks.

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

#62
post #8

Earlier quoted context omitted.

Because the problem is mostly about the reputation of the IP address. Setting up an email server is somewhat easy. Ensuring that other servers consider yours as legitimate that is the problem.

Spam is often sent from big providers, too. For several years I hosted my email the “middle ground” way (i.e., relaying outgoing mail via Google Workspace), and despite using DMARC correctly it was not infrequent that my emails would go to spam (even to GMail boxes) or never show up at all. Obviously GMail is such a giant that email providers have to be very careful when blocking it, but enough spam comes from there…

I have had very similar experiences.

Doing things perfectly and building up "reputation" helps a lot.

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

#63
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…

For me, thinking about potential deliverability issues is just too stressful. Even if it works 99% of the time, who knows how important the remaining 1% of emails will be. Personally, having control over my own domain is a good-enough middle ground.

But there's no deliverability guarantee with such a setup either. AIUI the premise of this thread is that the chances of delivery are higher with it, which may be the case (especially taking into account possibilities of misconfiguration on the sender's side), but that's precisely what made me to wonder about a survey/statistics once again: I wonder whether there's actually an observable difference.

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

#64
I'm going to write this assuming you're a non-technical professional, lawyer perhaps, looking for a private email solution that doesn't rely on third parties.

Bottom line: There's no "middle ground", any middle ground you cede is allowing a third party some kind of access. Hosting your own email has become expensive and time-consuming (although IMHO it's still extremely worthwhile, and I do it in spite of what a pain in the ass it is). Be prepared to spend at least $50/mo and at least 6 hours in setup and 1-2 hours a month debugging if you do it personally. Or you can find someone to help (see below). You need your own IP address. You need a dedicated box, not a VPS. And check the IP address in advance to make sure it's clean, and not blacklisted. Tell the datacenter you're going to be doing email and ask them if they're okay with that for a clean IP. Use https://mxtoolbox.com/blacklists.aspx to test the IP address they're offering you, or IPs in their range. Unlike some people are saying, you should never do this off a VPS if you have an interest in keeping the email secure and functioning for a long time.

My personal go-to would be dedicated hosting in the Netherlands, Switzerland, Isle of Man or Norway. Clean IPs, your own box, start with a clean server. But then you're talking $250/mo or so.

If you don't know how to set it up, there are people who can do it for you. You will need to essentially trust that person with access to all your correspondence, but if they do it properly, no one at the server farm[0] or elsewhere will have access to your correspondence... which puts you in the 0.01% of people on earth whose email isn't read by big tech companies.

[0] -who doesn't physically access the server: Look for ones in cages and ask who has physical access and why.

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

#65
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…

I can only contribute my own experience. I have a dedicated server with an IP address in a datacentre, with approx 6 users using my email server for their primary email. DKIM/DMARC/SPF all configured correctly. I also have policies that suspend logins for accounts if they send too much in a certain timeframe, because this is a pretty good indicator of account compromise. The limits would never be hit by humans.

I've had three issues. The first was delivering to outlook.com, but this was temporary and resolved relatively quickly: I simply contacted their support. At the time, they didn't bother to validate DKIM or DMARC according to their headers.

The second was a sender sending to us with a misconfigured SPF policy. I had quite strict rules that spf failure => user's junk folder that I had to relax, but I also had a discussion with the admins at the sending company to explain the issue.

The third was yahoo. For reasons known only to them, they decided that IPs they've never seen before will be blocked by returning an smtp deferral that is permanent, which is bad for legitimate mail servers because the email remains stuck in the mail queue forever. I ended up discussing this with their support also and after some discussion that block too was removed.

That's pretty much it. I receive dmarc reports now from many providers so I've an idea what percentage of our email is quarantined or rejected (none). I've been running email since 2011, for my own main email and a few others. I don't think deliverability is that much of an issue and I was able to resolve all the problems I've had in 10+ years of doing this by emailing support, explaining myself and asking to be unblocked. Usually this simply resulted in "OK but if you do bad things we will block you no guarantee of inbox delivery etc etc etc". That's fine. It seems that there is a large degree of per-account spam filtering as well at the big providers mapping to individual users' preferences.

Of course, if you don't set up SPF/DKIM/DMARC, or you have an IP with poor reputation (you can check the DNSBL) or worse a residential address, you will have trouble. I would generally look for a provider that has a relatively strict acceptable use policy, and in particular doesn't allow VPN endpoints to be run from their infra for your email, to reduce the chances your IP has a terrible reputation with the big providers. Also, join all the sender programmes, set reverse dns, don't let your users do things like send bulk email and that will reduce many of the problems.

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

#66
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 gma…

I also use SES for outbound. Haven't even thought of my selfhosted setup (run through Synology's MailPlus) since I first turned it on more than two years ago.

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

#67

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…

[deleted]

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

#68

I'm going to write this assuming you're a non-technical professional, lawyer perhaps, looking for a private email solution that doesn't rely on third parties. Bottom line: There's no "middle ground", any middle ground you cede is allowing a third party some kind of access. Hosting your own email has become expensive and time-consuming (although IMHO it's still extremely worthwhile, and I do it in spite of what a pain…

To prevent 3rd party access you need to not only host your own email but all recipients of your mail need to be self hosted as well. Unless you are providing everyone you correspond with their own account, 3rd parties will be involved.

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

#69
I use a free Gmail account as my mail client and direct all my custom domains from Fastmail to Gmail. Messages are delivered very quickly and I don't have spam issues.

Truth is I like Gmail but I think Google have dropped the ball with, "Let me point all my custom domains to a Gmail account. I would even pay you but I don't want Workspace".

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

#70

I'm going to write this assuming you're a non-technical professional, lawyer perhaps, looking for a private email solution that doesn't rely on third parties. Bottom line: There's no "middle ground", any middle ground you cede is allowing a third party some kind of access. Hosting your own email has become expensive and time-consuming (although IMHO it's still extremely worthwhile, and I do it in spite of what a pain…

To prevent 3rd party access you need to not only host your own email but all recipients of your mail need to be self hosted as well. Unless you are providing everyone you correspond with their own account, 3rd parties will be involved.

No, you just have to be aware of who you're sending to, and encrypt appropriately. I mean obviously if I send to someone @gmail, they're going to know I sent that person an email. But they can't scan my inbox for keywords.
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