25 votes

"You should not run your mail server because mail is hard"

14 comments

  1. skybrian
    Link
    Beware: the headline is the opposite of what the article is about. (It's saying that it's a myth that running your own email server is hard.)

    Beware: the headline is the opposite of what the article is about. (It's saying that it's a myth that running your own email server is hard.)

    16 votes
  2. jcdl
    Link
    I really want to see some legislation that makes it illegal to silently filter email. Sure, it's reasonable for Google or Microsoft to throw it in spam as long as it isn't silently deleted. It...

    I really want to see some legislation that makes it illegal to silently filter email. Sure, it's reasonable for Google or Microsoft to throw it in spam as long as it isn't silently deleted. It would just be nice if they sent a helpful reply to the postmaster address to explain why it was filtered, with suggested actions to take to adjust your server configuration or a way to file a complaint.

    This will never happen and email as an open protocol will die. I can only imagine anti-discrimination AI laws having any effect on this problem.

    Imagine if small mail courier services weren't allowed to exist? Sorry, we may have disappeared your package upon arrival because it wasn't brokered through a FedEx approved mail carrier.

    10 votes
  3. [2]
    envy
    Link
    It is hard running a mail server and avoiding the various spam detections that view unknown email servers with great suspicion.

    It is hard running a mail server and avoiding the various spam detections that view unknown email servers with great suspicion.

    8 votes
    1. heady
      Link Parent
      I have never attempted configuring my own server but I have used WordPress event management and mailing list plugins. I faced constant issues with spam detection and eventually resorted to mailchimp.

      I have never attempted configuring my own server but I have used WordPress event management and mailing list plugins. I faced constant issues with spam detection and eventually resorted to mailchimp.

      4 votes
  4. [2]
    pallas
    Link
    As much as this article seeks to be encouraging, I would really like to see some strong research showing that rDNS + SPF + DKIM is enough to reliably avoid the Google and Microsoft spam filters....

    As much as this article seeks to be encouraging, I would really like to see some strong research showing that rDNS + SPF + DKIM is enough to reliably avoid the Google and Microsoft spam filters. This has anecdotes and simple statements that such a setup is sufficient, while I've equally heard recent anecdotes from people saying that rDNS + SPF + DKIM is not enough, and that they had to stop using personal SMTP servers because Gmail consistently treated all their emails as spam.

    I also worry that the author's argument, "Big Mailer Corps are not worried about you but are worried about big senders harassing their users," is undermined by their own argument later that it's in the interest of such companies to discourage independent SMTP servers, because the "more people are discouraged, the more people will eventually subscribe to their services." No, they are not worried about you spamming their users, but they do want your business, and I expect they are worried about the threat easy in-house servers pose to their business model.

    As an example, we're currently trying to figure out how to handle email for our research group, as our university's email system is not fit for our purposes. The major deciding factor in our discussion is, unsurprisingly, whether Gmail and Office365 will actually deliver our emails if we run our own SMTP server, or whether we will need to go with a provider. Having spam filters that hinder independent SMTP servers certainly helps their SMTP provider businesses; spam filters are opaque and inconsistent enough, too, that it could be difficult to show that this was actually being done. That Gmail and Office365 appear no longer to have any way to turn off spam filtering without circuitous means adds to the problem.

    It's possible that the problem here is that, as the author suggests, very small servers, that seem to be personal (eg, from dynamic IPs, but not spammy content), may escape spam filters in order to avoid the appearance of draconian filtering, while larger, more reputable servers, which are more likely to be run by potential customers, are filtered. In tests of our university's Office365 email system, for example, we found that it routinely spam-filters emails from the in-house SMTP servers of two much more prestigious universities two of us are affiliated with, despite rDNS, SPF, DKIM, academic TLDs, and recognizable domains. Yet sending emails from an SMTP server on one of my computers, with SPF and DKIM, but without rDNS, on a dynamic, residential IP, gets through without a problem.

    7 votes
    1. Akir
      Link Parent
      My experience matches yours; when the company I worked for had me set up our own SMTP server, out mail would be filtered out. Sometimes it didn't even make it to spam, which is really bad for...

      My experience matches yours; when the company I worked for had me set up our own SMTP server, out mail would be filtered out. Sometimes it didn't even make it to spam, which is really bad for e-commerce because it makes you seem untrustworthy to some. After switching to a commercial email service, complaints of missing emails went away almost entirely.

      2 votes
  5. [6]
    weystrom
    Link
    Well, as I've mentioned here, I'm hitting the last part of the "myth", even though everything is correctly configured and my IP is clean.

    Well, as I've mentioned here, I'm hitting the last part of the "myth", even though everything is correctly configured and my IP is clean.

    6 votes
    1. [5]
      cmccabe
      Link Parent
      I self-host and have never had a problem making it into Gmail inboxes. But Outlook.com is another story. No matter how well configured a small email provider is, It seems like Outlook files them...

      I self-host and have never had a problem making it into Gmail inboxes. But Outlook.com is another story. No matter how well configured a small email provider is, It seems like Outlook files them in the spam directory.

      For Google, you can test your server with: https://postmaster.google.com

      I’m not sure if there is an equivalent for Outlook or other Big Corporate Mailers. But I’d love to hear about them if anyone knows others.

      3 votes
      1. pallas
        Link Parent
        That appears to helpfully tell you very little unless you have large server. It is currently showing me absolutely nothing. From the help pages: The situation with Gmail is better than Outlook, at...

        For Google, you can test your server with: https://postmaster.google.com

        That appears to helpfully tell you very little unless you have large server. It is currently showing me absolutely nothing. From the help pages:

        Most of the Postmaster Tools dashboards will display data only when there is a sizable daily volume of email traffic (up to the order of hundreds) coming from your Authentication Domains and/or certain other conditions, in place to prevent abuse.

        The situation with Gmail is better than Outlook, at least, as you point out.

        4 votes
      2. [3]
        weystrom
        Link Parent
        I've registered both with gmail and outlook. Haven't checked outlook, but with gmail it made no difference. Here's the link for outlook.com postmaster tools:...

        I've registered both with gmail and outlook. Haven't checked outlook, but with gmail it made no difference.

        Here's the link for outlook.com postmaster tools:
        https://sendersupport.olc.protection.outlook.com/pm/

        1 vote
        1. cmccabe
          Link Parent
          Thanks. I just found that too and worked through the sign up. Unfortunately no immediate impact. Microsoft seems to rely pretty heavily on their own reputation calculation for hosts, and I suspect...

          Thanks. I just found that too and worked through the sign up. Unfortunately no immediate impact. Microsoft seems to rely pretty heavily on their own reputation calculation for hosts, and I suspect it's heavily weighted against small time self-hosters. But I also see @pallas' comment below which contradicts this.

          1 vote
        2. cmccabe
          Link Parent
          I also found via linuxbabe.com that Microsoft has a sender information form that you can use to report that your email is being incorrectly marked as spam. I had to try submitting this form...

          I also found via linuxbabe.com that Microsoft has a sender information form that you can use to report that your email is being incorrectly marked as spam. I had to try submitting this form several times before I stopped getting an "Error, try again later" message. I'll report back if this has a positive impact.

  6. [2]
    calm_bomb
    Link
    I wanted to do it for myself, but I don't have the time. Also, I have a friend who's got an email server for just two email addresses and it's more work cleaning and trying to sort the spam than...

    I wanted to do it for myself, but I don't have the time. Also, I have a friend who's got an email server for just two email addresses and it's more work cleaning and trying to sort the spam than it's worth it. I prefer paying for something like protonmail or tutanota than having to maintain a "simple email server."

    3 votes
    1. 0lpbm
      (edited )
      Link Parent
      I'm using purelymail for my domains. They take care of the difficult bits, you just need to add the proper DNS entries to your registrar/dns provider (which they generate for you). You pay...

      I'm using purelymail for my domains. They take care of the difficult bits, you just need to add the proper DNS entries to your registrar/dns provider (which they generate for you). You pay (mostly) for space, which if you're being judicious with what you keep is not much at all.

      I've also heard good things about migadu.com though I've never used them.

      3 votes