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The “mail is hard” myth

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221–230 of 311 posts

Re: The “mail is hard” myth

#221

Earlier quoted context omitted.

> People sending personal emails will be happy to burn a penny of CPU time as "postage" but spammers won't be able to send their spam profitably The problem with this idea is that spammers don't use their own computer, they borrow other people's computers to send the spam. It also heavily penalizes people who legitimately need to send bulk email.

> It also heavily penalizes people who legitimately need to send bulk email. Aka spammers.

(Note: deleted and moved here because I put it in reply to the wrong comment)

I work for an email marketing provider (opinions my own, obviously), and I was extremely surprised how many people genuinely want to receive lots of commercial bulk marketing email. And by "want to" I don't mean "don't mark as spam", I mean "continually sign up for different marketing newsletters, and consistently use links in newsletters/marketing emails to make purchases from multiple companies". It's an alien phenomenon to me, and it may be a minority of bulk email, but it definitely is useful to a lot of people. Maybe it's their equivalent of coupon-clipping-based shopping, or maybe they just like learning about things to buy in that format? I have no idea.

That aside, the last thing an email marketing platform wants to do is send spam. Every time someone marks an email such a provider sends as spam, the reputation of their sending addresses is damaged, and therefore their ability to deliver mail to aforementioned people who want to receive them (and therefore the ability of the marketing platform to make money by facilitating that kind of desired email) is jeopardized.

TL;dr there's bulk marketing email and then there's spam, and surprisingly little overlap (and overlapping incentives) between the people who send each.

Re: The “mail is hard” myth

#222
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 fo…

> None of my emails are considered as spam, and I haven't touched the mail configuration since.

Sounds like you never actually tried to measure the delivery rates of your outgoing email. No email server is actually able to get 100% of its outgoing mail past spam filters.

I've ran my own email server for a few years and I can confirm that the article is making false claims. It's incredibly difficult to deliver email as a low volume sender. The article falsely claims that it's not difficult and that people simply haven't tried it. Well guess what, I did try it - for years - with countless hours sank into it.

I wrote a blog post documenting my numerous, unsuccessful efforts to get my email delivered. I wish people would stop spreading these baseless falsehoods.

https://www.attejuvonen.fi/dont-send-email-from-your-own-ser...

Re: The “mail is hard” myth

#223
post #99
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…

You can't actually measure deliverability with dmarc reports. They will only tell you the portion of emails that are bounced, but they don't differentiate between email in inbox and email in spam folder.

Re: The “mail is hard” myth

#224
post #112

A mail server is hard. Writing applications is hard. Designing a website is hard. Professional work is hard. But setting up your initial mail server is not hard. Read some guides (ahem: https://flurdy.com/docs/postfix ), fix a lot of typos, and you're up an running. Same with developing the initial version of an application, or designing the first draft. Not rocket science. Not easy but not that hard for an experienc…

> If you just want a reliable mail service, just use... non-Fastmail options that are a lot cheaper for multiple mailboxes and provide more, like Posteo, Mailbox.org, Runbox.com, Mailfence, Migadu, etc.

One of the "more" things many other services provide is far better privacy. European law is much more protective of human rights than American (where Fastmail hosts its servers and emails are "business records") or Australian (where Fastmail is located and where even warrant canaries are illegal).

Re: The “mail is hard” myth

#225
post #112

A mail server is hard. Writing applications is hard. Designing a website is hard. Professional work is hard. But setting up your initial mail server is not hard. Read some guides (ahem: https://flurdy.com/docs/postfix ), fix a lot of typos, and you're up an running. Same with developing the initial version of an application, or designing the first draft. Not rocket science. Not easy but not that hard for an experienc…

I also use Fastmail to host my calendar and contacts - next to my email. I enjoy the web interface and lI especially like that the iOS integration just works.

Re: The “mail is hard” myth

#226
post #136

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 w…

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

This is incorrect. By using Gmail you've lost several legitimate incoming emails due to their horrendous spam filtering. It's just hard to be aware of the emails you've never seen, so you think nothing ever failed.

In addition, if you are relying on @gmail addresses, you run the catastrophic risk of permanently losing access to your email with no-one to call for help. There's so many instances of this happening that you can't even call them isolated instances. All it takes is for Google's ML algorithms to think that you have violated their T&C somehow. And poof! Everything is gone.

Re: The “mail is hard” myth

#227
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 fo…

New domains and new IPs are penalized heavily by most services' spam filters.

My guess is that a lot of people try it, have poor delivery rates, and abandon the effort before they have enough time to develop decent domain & IP reputations.

I've been running my own personal mail servers since 1995, on my current IP addresses since ~2016. If I add a new domain to my configuration, it takes 1-2 weeks before Gmail will reliably accept mail from it. Once I wait that out, delivery is mostly flawless.

Re: The “mail is hard” myth

#228
post #35

Earlier quoted context omitted.

There's also a huge difference between setting up a properly configured server and actually getting things delivered. The big ones (MS, Google) mark your mail as spam even with SPF, DMARC, DKIM and the like. Even on the service I use (purelymail.com) the low volume of mail and the fact that it's less than a year old means that even when I email them first, the replies are sometimes marked as spam.

Running my own for about 2 years now. Spf dMarc and dkim set it is accepted by all mail providers. I also get daily reports from Google how well it behaves

> Running my own for about 2 years now. Spf dMarc and dkim set it is accepted by all mail providers. I also get daily reports from Google how well it behaves

This is false. The dmarc reports from Google do not actually give you the portion of email that is placed in recipients' spam folder.

Re: The “mail is hard” myth

#229
For me mail is hard because software is convoluted. I need to install for a minimal usable personal mail server: SMTP server (postfix), IMAP server (dovecot), DKIM software (OpenDKIM), Spam filter (Spam Assassin). Also I would likely need to install Procmail for some basic mail sorting. So that's 3 huge projects and 2 small projects. They need to hook up with each other. I need to learn configuration files for every of those projects. Add to that dozen of different DNS things (and, recently, HTTPS thing), that you need to configure. Also TLS certificates. Well, that's a daunting task for me. Some kind of simple personal web server software which does it all (may be not for 100k users scale), runs on low end VPS server (10 MB RAM consumption) and requires zero configuration for typical use-cases would help a lot.

And, yeah, don't tell me that delivering is easy. I did everything right, DKIM, SPF, PTR, all those things. No black lists. Gmail still does not deliver my mails sometimes.

Re: The “mail is hard” myth

#230

Earlier quoted context omitted.

> 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 fo…

> 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. Not sure about OP, but many people have tried it and it is a PITA. Even once you have everything setup right (SPF, DKIM, etc.), you still have to deal with IP issues. I ran my own mail server for years (actually, still do for incoming) and it worked fine for about 10 yea…

UCEPROTECT was the pits and its operators were unprincipled lowlifes. Luckily they (like all the pay-to-delist BLs) never got more than minimal traction, so ignoring them and their BS mostly worked ('course you needed a /19 to be effective at doing that)
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