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So, I've run simple Postfix + Django emails for transaction confirmations, password resets, and in a few cases, 2FA, for a bunch of different sites I've worked

So, I've run simple Postfix + Django emails for transaction confirmations, password resets, and in a few cases, 2FA, for a bunch of different sites I've worked on since I started my freelance business 6 years ago. I've never had a single complaint that my emails weren't delivering, nor has an email ever gone to spam folder in testing. How did I do it? The answer is simple: I didn't send any spam! The last time this came up on Hacker News, one of the top comments was something to the effect of "we did double confirmation and a variety of other measures to avoid being marked as spam, but ultimately the entire time we're just one bad email campaign away from being blacklisted". One bad email campaign? Is there any other kind? That's just spam. The user didn't say this, but I'd bet money their "double confirmation" starts with a default-checked checkbox with small text asking for permission to send emails. Every time I've talked to someone who has problems with email deliver-ability, if I dig into what they're doing, it quickly becomes clear to me that they're sending spam, but they're so indoctrinated in corporate culture that they don't even know that what they're sending is spam. Here's some translations for you: Marketing email = spam. Lead generation = spam. In most cases, newsletter = spam. Sale announcement = spam. Promotion = spam. I'm not claiming my experience is universal. I'm sure that there is a non-zero percentage of sites sending legitimate emails getting marked as spam. But it seems to me that more often than not, the reason your emails are marked as spam is that they are, in fact, spam. And most strategies people discuss for avoiding being marked as spam, are just avoiding the most obviously egregious forms of spam, and finding users with higher tolerance for spam.

angst_ridden 4y ago
I run a site for a large corporate client. People can sign up to get a quote from a regional dealer for a specific type of complex product. To get a quote, they have to fill out several forms, and select detailed specification, etc, and choose email as the way to deliver the quote. We regularly have users flag the email they receive from this process as spam. I have personally called to follow up in some cases to understand if our service was being abused or what the issue was. It was eye-opening. One user said "oh, yeah, I wanted that when I filled out the form but not when I got the email." Several marked the proposal as spam because they didn't like the final quote that was put together from their requirements. Several said things like "I get too much email" and when pressed as to why they checked the box that said they wanted their quote delivered as an email replied that they didn't know, or they changed their minds, or they didn't want HTML email, or they didn't want a plain-text email, or their name was not in the subject line of the email, or that their company name was not in the subject line of the email. This is a very low volume, very expensive, highly technical product. We're talking maybe a dozen requests per day nationwide. So those people flagging the emails as spam have a significant impact on the overall deliverability to services like GMail.
- bcrosby95 4y ago
  Yeah, unfortunately customers can be pretty shitty. We've had a lot of interesting experiences with this and also paid subscriptions - things like significant others accusing us of a massive fraud, soon afterwhich the person who signed up for the service to ask to be reinstated. That said, if you can get people on the phone, they tend to be much kinder. I think most people think they're just shouting into some empty void.
  - Spivak 4y ago
    I think trying to frame "customers mark unwanted email as spam" as a customer problem is just shouting at a river at this point. How I design my, admittedly not corporate, email delivery system is to require the user explicitly click "Send this to my email" every single time. No email is sent without a user clicking a button painfully explicitly asking for it. Honestly treating e-mail like sex where it requires enthusiastic continuous consent feels like it should have always been this way. It's really not that hard to have a button and have receipts/tracking to only be on your account page unless they ask for it.
    - amatecha 4y ago
      Yeah but like, the guy who mentioned the customers marking emails as spam even though they requested it, did the exact same thing. They consciously solicited a quote and specifically asked for it to be delivered by email, and then for some unknowable reason, marked it as spam despite having completely 100% consented to receiving the email.
      - Cyphase 4y ago
        It's like they're using it as a delete button.
      - denton-scratch 4y ago
        > for some unknowable reason, marked it as spam despite having completely 100% consented to receiving the email Ordinary users aren't very interested in what is and isn't spam (nor are legislators, for that matter). It doesn't help that organisations like DMA lobby to tinker with definations. Unsurprisingly, a large proportion of users think spam is just "email I don't want". So they click on "mark as spam".
thesausageking 4y ago
I run an email domain for myself and three friends. I set it up 10+ years ago and originally it was for ~15 people. It's only personal email and no one uses it for marketing or anything even remotely shady. We setup DKIM and all of the similar best practices. In the last 6-12 months, we've had lots of issues with gmail marking our messages as spam for users we haven't emailed before. And what sucks about it is there's nothing you can do. People assume it's your fault for being weird and not using Gmail or outlook.com. And there's zero way to contact Google or submit information to convince them you're legitimate. I believe in an open, distributed internet. I don't think it's good that we're moving towards a world we're the core protocols that defined the internet are being replaced by proprietary versions controlled by a handful of trillion dollar companies.
- flippinburgers 4y ago
  This makes me sad the "old" internet has been dead for a while it seems. I also run my own email "server" but mostly only use it as an inbox so I don't know how things have evolved over time. At some point I signed up for some google feature that will send me a reliability report, zipped, xml from google. I don't remember the details and, yeah, I haven't ever tried to reach out to google but based on their products I imagine it is impossible to actually contact anyone.
jimmaswell 4y ago
You can be judged for your entire IP range if you use the wrong VPS. DigitalOcean is one such place. They put all their domains on spamhaus by default, which you can get removed, but it seems MicroSoft and some others still don't like you just for being from DigitalOcean. I never sent any spam from my IP that I had for a decade but ran into this when I tried delivering to MS emails even after getting removed from spamhaus. Setting up a gmail relay that retained my from: address did the trick though.
- kerkeslager 4y ago
  All my sites are hosted on Digital Ocean?
- wrycoder 4y ago
  I’ve got a mail server running on DO. While Google sometimes spam bins Mail from my server, the server has never been listed on spamhaus. I don’t care about MS, so I don’t know how delivery there is.
- account42 4y ago
  That's been my experience too. Google mostly accepts things as long as the domain isn't brand new, but Microsoft will just not work with you because they don't like the IP block you are on.
denton-scratch 4y ago
> we did double confirmation "Double confirmation" is spammer-speak. The correct formulation is "confirmed opt-in".
- kerkeslager 4y ago
  If you're saying the same thing it's still spammer speak.
- account42 4y ago
  The correct thing to do is user-initiated subscription signup. That means the e-mail subscription itself must be user-initiated and not part of or blocking some other flow.
fareesh 4y ago
What VPS provider do you use?

angst_ridden 4y ago

I run a site for a large corporate client. People can sign up to get a quote from a regional dealer for a specific type of complex product. To get a quote, they have to fill out several forms, and select detailed specification, etc, and choose email as the way to deliver the quote. We regularly have users flag the email they receive from this process as spam. I have personally called to follow up in some cases to understand if our service was being abused or what the issue was. It was eye-opening. One user said "oh, yeah, I wanted that when I filled out the form but not when I got the email." Several marked the proposal as spam because they didn't like the final quote that was put together from their requirements. Several said things like "I get too much email" and when pressed as to why they checked the box that said they wanted their quote delivered as an email replied that they didn't know, or they changed their minds, or they didn't want HTML email, or they didn't want a plain-text email, or their name was not in the subject line of the email, or that their company name was not in the subject line of the email. This is a very low volume, very expensive, highly technical product. We're talking maybe a dozen requests per day nationwide. So those people flagging the emails as spam have a significant impact on the overall deliverability to services like GMail.

bcrosby95 4y ago
Yeah, unfortunately customers can be pretty shitty. We've had a lot of interesting experiences with this and also paid subscriptions - things like significant others accusing us of a massive fraud, soon afterwhich the person who signed up for the service to ask to be reinstated. That said, if you can get people on the phone, they tend to be much kinder. I think most people think they're just shouting into some empty void.
- Spivak 4y ago
  I think trying to frame "customers mark unwanted email as spam" as a customer problem is just shouting at a river at this point. How I design my, admittedly not corporate, email delivery system is to require the user explicitly click "Send this to my email" every single time. No email is sent without a user clicking a button painfully explicitly asking for it. Honestly treating e-mail like sex where it requires enthusiastic continuous consent feels like it should have always been this way. It's really not that hard to have a button and have receipts/tracking to only be on your account page unless they ask for it.
  - amatecha 4y ago
    Yeah but like, the guy who mentioned the customers marking emails as spam even though they requested it, did the exact same thing. They consciously solicited a quote and specifically asked for it to be delivered by email, and then for some unknowable reason, marked it as spam despite having completely 100% consented to receiving the email.
    - Cyphase 4y ago
      It's like they're using it as a delete button.
    - denton-scratch 4y ago
      > for some unknowable reason, marked it as spam despite having completely 100% consented to receiving the email Ordinary users aren't very interested in what is and isn't spam (nor are legislators, for that matter). It doesn't help that organisations like DMA lobby to tinker with definations. Unsurprisingly, a large proportion of users think spam is just "email I don't want". So they click on "mark as spam".

thesausageking 4y ago

I run an email domain for myself and three friends. I set it up 10+ years ago and originally it was for ~15 people. It's only personal email and no one uses it for marketing or anything even remotely shady. We setup DKIM and all of the similar best practices. In the last 6-12 months, we've had lots of issues with gmail marking our messages as spam for users we haven't emailed before. And what sucks about it is there's nothing you can do. People assume it's your fault for being weird and not using Gmail or outlook.com. And there's zero way to contact Google or submit information to convince them you're legitimate. I believe in an open, distributed internet. I don't think it's good that we're moving towards a world we're the core protocols that defined the internet are being replaced by proprietary versions controlled by a handful of trillion dollar companies.

flippinburgers 4y ago
This makes me sad the "old" internet has been dead for a while it seems. I also run my own email "server" but mostly only use it as an inbox so I don't know how things have evolved over time. At some point I signed up for some google feature that will send me a reliability report, zipped, xml from google. I don't remember the details and, yeah, I haven't ever tried to reach out to google but based on their products I imagine it is impossible to actually contact anyone.

jimmaswell 4y ago

You can be judged for your entire IP range if you use the wrong VPS. DigitalOcean is one such place. They put all their domains on spamhaus by default, which you can get removed, but it seems MicroSoft and some others still don't like you just for being from DigitalOcean. I never sent any spam from my IP that I had for a decade but ran into this when I tried delivering to MS emails even after getting removed from spamhaus. Setting up a gmail relay that retained my from: address did the trick though.

kerkeslager 4y ago
All my sites are hosted on Digital Ocean?
wrycoder 4y ago
I’ve got a mail server running on DO. While Google sometimes spam bins Mail from my server, the server has never been listed on spamhaus. I don’t care about MS, so I don’t know how delivery there is.
account42 4y ago
That's been my experience too. Google mostly accepts things as long as the domain isn't brand new, but Microsoft will just not work with you because they don't like the IP block you are on.

denton-scratch 4y ago

> we did double confirmation "Double confirmation" is spammer-speak. The correct formulation is "confirmed opt-in".

kerkeslager 4y ago
If you're saying the same thing it's still spammer speak.
account42 4y ago
The correct thing to do is user-initiated subscription signup. That means the e-mail subscription itself must be user-initiated and not part of or blocking some other flow.

fareesh 4y ago

What VPS provider do you use?