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The “mail is hard” myth

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Re: The “mail is hard” myth

#131

Post by purple_ducks »

bad_user wrote: post #78
xrisk wrote: post #72

Earlier quoted context omitted.

This is a great analogy. Why do more work when you can get the same result with less effort?

If you're living at the country side, producing your own milk is healthier, can be a good hobby while you're young and a great occupation after you're retired. Manual labor is good exercise and can be fulfilling. But I'd probably go with goats instead. I don't think maintaining your own email server can be very fulfilling, but hobbies are a matter of taste.

> producing your own milk is healthier

How's that?

Re: The “mail is hard” myth

#132

Post by dorgo »

dwd wrote: post #99
skrause wrote: post #16

I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being marked as spam. Especially if you don't actually send a lot of mail, so you can never really build up a good IP reputation. That's why I generally recommend a hybrid setup: Host inbound mail completely by yourself so that you have full control, but ship off outbound…

I would also recommend setting up a dmarc record so you can monitor your deliverability. Spam however is still a hassle and you're never going to match Gmail or Outlook when you're small. Say it takes a few hundred identical spammy emails to trigger a filter. For Gmail it means the chance of receiving that spam is less than 1 in a million. If you're small and managing say a 1000 users - a large percentage will end up…

>Say it takes a few hundred identical spammy emails to trigger a filter

Wait, is this really the way how spam filters work? All I need to do is to add a random number to all emails to bypass spam filters?

Re: The “mail is hard” myth

#133

Post by bt848 »

jdboyd wrote: post #105
akerl_ wrote: post #34

Earlier quoted context omitted.

The article handwaves this by pointing out that it’s “proof-of-work”. Which is a fancy way of saying “it requires a bunch of work, continuously as the rules change over time”. Which is why I’d consider it “hard” to run my own mail server. The complexity of running a daemon with a config file isn’t the issue, nor is it that any individual task of SPF/DKIM/etc is complex. It’s that I generally want to put 0% of my time…

In my experience of over 15 years, the "rules" have only changed 3 times since I started. First to require good reverse DNS, then to require SPF, last to require DKIM. The transition on each of those was generally several years with plenty of publicity.

That hardly covers it. The problem is that who "you" are, your identity as a sender, is not entirely within your control. The big mail operators figure in a ton of stuff, like the reputation of your subnet - /24 maybe, or /96, it's an approximation - or the reputation of your AS, your domain registrar, all kinds of stuff. If the guy on the next IP over is sending spam that's going to pollute your reputation.

If you have your own ASN and your information is registered with reputable parties in lawful countries, you might not have much to worry about. If you are using a cheap cloud VPS service whose network is registered to a Romanian holding company, nobody will deliver your mail.

Re: The “mail is hard” myth

#134

Post by bt848 »

beams_of_light wrote: post #127
klingonopera wrote: post #13

Let's see... Postfix, Dovecot, SPF and OpenDKIM on the server-side, each of them with their own config. Then you've got to set up your domain, and domain headers on your domain host. Oh, DMARC is also another thing. Then, most ISPs will outright refuse to accept incoming mail from your IP address, since they've basically changed from blacklisting to whitelisting. So you've also got to relay your outgoing mail via you…

Trying to avoid the landmines of blacklisting is really the biggest peril in all of it. I refuse to move a company I support away from GSuite to self-hosted, because I have a high level of confidence that just one person sending a lot of mail to another person outside the company could result in our domain ending up in RBLs, which is very difficult to reverse. Running a mail server in 2019 is not something I need the…

That's amusing because the bigs all ignore RBLs. RBLs are only used by the little operators.

Re: The “mail is hard” myth

#135

Post by paulie_a »

ekianjo wrote: post #93
xrisk wrote: post #72

Earlier quoted context omitted.

This is a great analogy. Why do more work when you can get the same result with less effort?

> This is a great analogy. Why do more work when you can get the same result with less effort? If you wake up one day and the only email you can use is the one you can get from a major provider, you have just become a consumer.

Honestly what's wrong with that?

Re: The “mail is hard” myth

#136

Post by gfodor »

Number of times I have had the problem of "email not working for some reason" since switching to gmail ~20 years ago: zero.

Number of times I had this problem when running my own mail server (and presumably would have today): non-zero.

There's your entire explanation as to why this is a losing battle. Just one incident of an email delivery problem probably outweighs any privacy risk wrt using a centralized provider wrt email. That prior could change if there is a privacy related incident with these providers, but so far their track record has been good.

Re: The “mail is hard” myth

#137

Post by LeonM »

lelf wrote: post #10

> but my mails will not reach my users at Big Mailer Corps Unfortunately this is not a myth. rDNS/DKIM/SPF/not in any greylists, but mail from you goes to Junk folder on GMail®, experienced that myself.

It is a myth.

The bigger mail providers (such as Gmail) are pretty strict on checking, and feedback is fairly limited. Thus, figuring out why you were flagged as spam is often difficult and frustrating.

There are so many subtle misconfigurations you can make with the way you have your DNS records set up, but really you need DMARC reports to figure out why your email is getting flagged.

It inspired me to build my startup :) We have successfully fixed dozens of email deliverability issues for our customers.

Re: The “mail is hard” myth

#138

Post by nathankunicki »

His assessment on how “Big Mail Corps” accept mail is plain wrong from my experience. When I ran my own mail server, I had SPF, DKIM, rDNS and strict DMARC setup correctly, and got 10/10’s on mail-tester.com.

Admittedly my main problems were with people on Microsoft hosted emails. They seem to run some kind of IP address based blacklist-by-default operation. My emails to Hotmail/Outlook.com users would randomly get either rejected or go straight to spam.

I went through countless online forms, Twitter conversations with clueless CSR’s who kept asking me what Outlook client settings I was using, and finding random people on LinkedIn I could message.

In the end the solution that seemed to work was to reach out separately to everyone I was sending an email to on Hotmail/Outlook.com and getting them to explicitly mark my email as not spam. After a while it seemed to take and stop rejecting/marking my emails.

Re: The “mail is hard” myth

#139

Post by AviationAtom »

gingerlime wrote: post #50
klingonopera wrote: post #13

Let's see... Postfix, Dovecot, SPF and OpenDKIM on the server-side, each of them with their own config. Then you've got to set up your domain, and domain headers on your domain host. Oh, DMARC is also another thing. Then, most ISPs will outright refuse to accept incoming mail from your IP address, since they've basically changed from blacklisting to whitelisting. So you've also got to relay your outgoing mail via you…

And if you try to host it on Digital Ocean, they actually block port 25 out, so you're out of luck... And you have to manage diskspace, backups, firewall/fail2ban, OS updates etc etc etc I'm in the same boat as you. Managed to grind my teeth and pull through something like this for my own use and family, but it was painful.

Pretty sure a message to them stating your intended use will result in the block being lifted

Re: The “mail is hard” myth

#140

Post by ogoffart »

skrause wrote: post #16

I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being marked as spam. Especially if you don't actually send a lot of mail, so you can never really build up a good IP reputation. That's why I generally recommend a hybrid setup: Host inbound mail completely by yourself so that you have full control, but ship off outbound…

> I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being marked as spam

Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it.

In fact, I used to think exactly like you when I originally set up my personal mail server and opted for the hybrid setup you suggest. However, when the third party service I used to send mail shut down a couple of years ago, I quiclky set up outbound mail on my own server. None of my emails are considered as spam, and I haven't touched the mail configuration since.

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