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    You do all of this, but then you still can’t get into the Gmail, Yahoo or Outlook inboxes. Why?

    Maybe the first email you sent (to a close friend, who happens to use Gmail) accidentally had a spam trigger word. Maybe the IP on your shared host was previously used by someone whose WordPress install got hacked and wound up sending spam. Maybe something else entirely! You’ll never know!

    Or maybe you did everything right and got lucky on all those details, and everything is working fine. But then some troll messes with you by maliciously filling out your form 200 times with bullshit email addresses that don’t exist. Are you doing double opt-in? Are you bounce-parsing to make sure you don’t re-send repeatedly to non-existent email addresses? How do you handle backoff on receiving domains that temporarily greylist you? Missing those details is going to hurt you too in the long run. The industry best practice is double opt-in for a reason, and if you want to do anything other than that, you’re fighting an uphill battle. It’s a battle you can still fight, but not an easy one.

    The current state of email deliverability is the end result of layers of good intentions, all collaborating to produce a worst-of-all-worlds situation for unsophisticated good actors. We can’t seem to solve it without unnecessarily re-enabling spammers, aside from “Give up hope and let a few centralized ‘trusted’ ESPs own our very concept of email.”

    I got stuck following this guide on how to startup… the next step after collecting e-mail addresses was sending something to them.

    Although all the best talking head VC-turned-bloggers (or bloggers-turned-VCs?) will tell you email marketing is a great idea, and that you’ve not really tried it until you’ve sent at least one hundred thousand emails, no one gives actual deep details of best practices for startup email marketing. If they did, and everyone followed the advice, it would be self-defeating for those who currently are reaping the benefits of the more sophisticated strategies.

    This article is still great. It is all accurate and good advice. As they say, it is “necessary but not sufficient”.

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      Yes, I agree entirely. I wrote about this a while ago:

      http://penguindreams.org/blog/how-google-and-microsoft-made-email-unreliable/

      Which I based off the “Hostel E-mail Landscape” blog post that’s references at the bottom of my post.

      I can understand why spam filters are so aggressive. I’ve looked through my spam trap and found some crazy good phishing sites, some carefully crafted Javascript ransomware and lots of other terrible things. Some of it makes it through, but at least I can identify and know what to do with it. Many average Internet individual cannot.

      It an attempt to keep people safe, e-mail is now terribly terribly unreliable, unless you’re one of the big players like Google, MS or Mailchimp. It’s the slow death of the distributed and federated web.

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        I rather hoped you’d chime in. ;)

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        Don’t forget DMARC and, if your server is available over IPv6, you need to also set up reverse DNS lookup for that too.

        Oh, and don’t set up automated forwarding of emails received by an account on your server to another account on GMail, because that will mark your domain as a spam source. Use POP3 or IMAP to fetch them instead.