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It's amazing how quickly people with strong feelings about email come out when any mention of self hosting is made. They can't prove a negative, but they valia

It's amazing how quickly people with strong feelings about email come out when any mention of self hosting is made. They can't prove a negative, but they valiantly try, often using the very points that are excellent reasons to self-host as reasons we should all just give up. "It doesn't work for me, so it won't work for you" is rather weak when the reasons aren't articulated, when generalizations are made without detail, when hardly any attempt at all was made to find the root of the problem. Your failure is not the same as my quarter century of success. They also tries to make everything all or nothing, which plainly lacks any imagination. I wouldn't want an admin on my staff who tries something, then gives up at the littlest of hurdles. There are plenty of issues, but there are also plenty of solutions. You're having issues sending because your netblock sucks and you don't have money for something better? Pay a few dollars to smarthost, for instance. With Google and Outlook, you get no determinism, no accessible logging, no clear view about their filtering rules, no assurance that your outgoing email won't get blocked, anyway, because of the tremendous amounts of spam these monopolies allow... We should encourage MORE people to self-host email, not less. We should never just assume the monopolies are the best we can do.

mcguire 5y ago
"Pay a few dollars to smarthost, for instance." Do you mean pay a few dollars to use someone else's email infrastructure? Or do you mean pay a few dollars more to set up a dedicated mail host in a better neighborhood?
gnopgnip 5y ago
You get access to logging etc. with an outlook business account
- jabroni_salad 5y ago
  Yup, between the message trace and just reading the headers I have not been wanting for visibility... and as the Exchange Online admin I've found that 99% of deliverability issues end up resting with the outside party failing to read their own infra's NDRs anyways.
- johnklos 5y ago
  Good to know! Thanks :)
draw_down 5y ago
jasode 5y ago
>"It doesn't work for me, so it won't work for you" is rather weak Maybe I missed it but I scrolled through the comments and I don't see anyone in this thread claiming the above. In fact, I see the people who had problems with personal mail server deliverability acknowledge that others may have success and "that's good for them."
- jagged-chisel 5y ago
  Seemed to me an inditement of the general malaise of all previous discussions, not only this one.
Dunedan 5y ago
> There are plenty of issues, but there are also plenty of solutions. You're having issues sending because your netblock sucks and you don't have money for something better? Pay a few dollars to smarthost, for instance. I do and outlook.com still gives a shit and doesn't accept incoming emails. There is also no way to get their attention for this issue, as they simply don't reply to complaints about that. How to solve issues like that? > We should encourage MORE people to self-host email, not less. We should never just assume the monopolies are the best we can do. That's something I can wholeheartedly agree with.
- dqv 5y ago
  What kind of mail are you sending? Are you getting anything on your abuse@ address? Are you getting any feedback on JMRP [0]? If all else fails, the mailop mailing list [1] can get you closer to someone on one of these networks to help. >There is also no way to get their attention for this issue, as they simply don't reply to complaints about that. How to solve issues like that? At one point, after getting one-too-many rejections for a particular recipient, I started sending the postmaster of the recipient’s service an email every time I needed to contact the recipient. That resolved the issue pretty quickly. You can always try annoying the postmaster. [0]: https://postmaster.live.com/snds/JMRP.aspx https://postmaster.live.com/snds/JMRP.aspx [1]: https://www.mailop.org/ https://www.mailop.org/
  - Dunedan 5y ago
    > What kind of mail are you sending? Just personal emails. Volume would be somewhere around one email per month or so. > Are you getting anything on your abuse@ address? Nope. > Are you getting any feedback on JMRP [0]? That seems to require a Microsoft account and that's something I neither have nor want. I believe sending emails has to work without having to register an account for each provider you're interacting with. > If all else fails, the mailop mailing list [1] can get you closer to someone on one of these networks to help. Thanks for the tip, although I'm not sure if I'm the right audience for this list, as I just run a personal mail server with very low volume. Funnily enough the "Best practices" section of the Mailop website contains a dedicated point (https://www.mailop.org/best-practices/#large-providers-gmail-microsoft-etc https://www.mailop.org/best-practices/#large-providers-gmail...) stating that there might be unresolvable issues when sending to large providers: > If you want to send mail to recipients who have accounts at big email providers, be aware that all of the above cannot guarantee that these providers won’t reject your mail, put it straight into recipient’s spam folder or just silently discard it - they just impose their own rules on anyone and you virtually can’t do anything about it. My guess is, that the reason for the problems is the same as quoted in another comment (https://news.ycombinator.com/item?id=29673347 https://news.ycombinator.com/item?id=29673347), stating that the mail volume is just too low for outlook.com to establish enough trust in the sending mail server. If you look around on the internet, there are plenty of other people with the same issues with outlook.com. To me it seems Microsoft is doing something fundamentally hostile to small mail servers there. Interestingly enough sending to Office 365 hosted email addresses works just fine.
dqv 5y ago
I've said elsewhere in the thread, but everyone has a circle of influence. Big Mail needs to maintain a reputation of being reliable. I can and have convinced people that e.g. Yahoo mail is not reliable for receiving mail and to stop using it. And those people will do the same with their people. I think that's why it's important for people to keep at it with these "artisanal mail servers" (with the help of mail packages that do automatic configuration). More people can pressure Big Mail and demand that they let us deliver our (legit) mail as smoothly and easily as possible.
- charcircuit 5y ago
  They also need to have a reputation of being able to block spam.
  - dqv 5y ago
    The issue is the spam still gets through on every single one of these providers, so that reputation isn’t nearly as important. Reliably receiving emails is. If that aspect of their reputation is damaged, it may never recover.
dheera 5y ago
Yes. I want to create a mail server that auto-rejects e-mail with externally hosted tracking pixels and returns a Mailer-Daemon error that tells the sender to re-send without malware. Of course with Gmail I disable automatic image loading to avoid being tracked, but I want to take a more active stance against the practice.
- CogitoCogito 5y ago
  What’s your method of detecting tracking pixels? Is it just as simple as scanning for size 1x1 images? I mean this as an honest question. I don’t really know variety of tracking pixels out there. Are there other similar things one should block?
  - dheera 5y ago
    I would just block all images loaded from external URLs, since any of them could be used for tracking, but the newsletters are less my concern, it's more the individuals that I would be concerned about, and they tend to be a almost-fully plain text e-mail with a 1x1 image from one of many well-known domains for tracking.
    - sgarman 5y ago
      Since it's an email isn't every image from an external url? Do you just mean blocking all images?
      - collinmanderson 5y ago
        Emails can have "inline" attachments, where an image can be attached in the body of the email itself. So the image shows up without any network access, but it's generally base-64 encoded (costing 4x space) and ends up using a lot of email storage space.
        sfoley 5y ago
        Base64 costs 1.3x space, not 4x.
micromacrofoot 5y ago
unfortunately as long as you’re sending email to other people you’re subject to Google’s filtering rules, so it may be easier to work with a provider that operates at a scale google cares about… it’s all a racket if you ask me… their algo can doom any individual self-hoster to perpetual spam hell and they’ve got zero service
deleted 5y ago
[deleted]

mcguire 5y ago

"Pay a few dollars to smarthost, for instance." Do you mean pay a few dollars to use someone else's email infrastructure? Or do you mean pay a few dollars more to set up a dedicated mail host in a better neighborhood?

gnopgnip 5y ago

You get access to logging etc. with an outlook business account

jabroni_salad 5y ago
Yup, between the message trace and just reading the headers I have not been wanting for visibility... and as the Exchange Online admin I've found that 99% of deliverability issues end up resting with the outside party failing to read their own infra's NDRs anyways.
johnklos 5y ago
Good to know! Thanks :)

draw_down 5y ago

jasode 5y ago

>"It doesn't work for me, so it won't work for you" is rather weak Maybe I missed it but I scrolled through the comments and I don't see anyone in this thread claiming the above. In fact, I see the people who had problems with personal mail server deliverability acknowledge that others may have success and "that's good for them."

jagged-chisel 5y ago
Seemed to me an inditement of the general malaise of all previous discussions, not only this one.

Dunedan 5y ago

> There are plenty of issues, but there are also plenty of solutions. You're having issues sending because your netblock sucks and you don't have money for something better? Pay a few dollars to smarthost, for instance. I do and outlook.com still gives a shit and doesn't accept incoming emails. There is also no way to get their attention for this issue, as they simply don't reply to complaints about that. How to solve issues like that? > We should encourage MORE people to self-host email, not less. We should never just assume the monopolies are the best we can do. That's something I can wholeheartedly agree with.

dqv 5y ago
What kind of mail are you sending? Are you getting anything on your abuse@ address? Are you getting any feedback on JMRP [0]? If all else fails, the mailop mailing list [1] can get you closer to someone on one of these networks to help. >There is also no way to get their attention for this issue, as they simply don't reply to complaints about that. How to solve issues like that? At one point, after getting one-too-many rejections for a particular recipient, I started sending the postmaster of the recipient’s service an email every time I needed to contact the recipient. That resolved the issue pretty quickly. You can always try annoying the postmaster. [0]: https://postmaster.live.com/snds/JMRP.aspx https://postmaster.live.com/snds/JMRP.aspx [1]: https://www.mailop.org/ https://www.mailop.org/
- Dunedan 5y ago
  > What kind of mail are you sending? Just personal emails. Volume would be somewhere around one email per month or so. > Are you getting anything on your abuse@ address? Nope. > Are you getting any feedback on JMRP [0]? That seems to require a Microsoft account and that's something I neither have nor want. I believe sending emails has to work without having to register an account for each provider you're interacting with. > If all else fails, the mailop mailing list [1] can get you closer to someone on one of these networks to help. Thanks for the tip, although I'm not sure if I'm the right audience for this list, as I just run a personal mail server with very low volume. Funnily enough the "Best practices" section of the Mailop website contains a dedicated point (https://www.mailop.org/best-practices/#large-providers-gmail-microsoft-etc https://www.mailop.org/best-practices/#large-providers-gmail...) stating that there might be unresolvable issues when sending to large providers: > If you want to send mail to recipients who have accounts at big email providers, be aware that all of the above cannot guarantee that these providers won’t reject your mail, put it straight into recipient’s spam folder or just silently discard it - they just impose their own rules on anyone and you virtually can’t do anything about it. My guess is, that the reason for the problems is the same as quoted in another comment (https://news.ycombinator.com/item?id=29673347 https://news.ycombinator.com/item?id=29673347), stating that the mail volume is just too low for outlook.com to establish enough trust in the sending mail server. If you look around on the internet, there are plenty of other people with the same issues with outlook.com. To me it seems Microsoft is doing something fundamentally hostile to small mail servers there. Interestingly enough sending to Office 365 hosted email addresses works just fine.

dqv 5y ago

I've said elsewhere in the thread, but everyone has a circle of influence. Big Mail needs to maintain a reputation of being reliable. I can and have convinced people that e.g. Yahoo mail is not reliable for receiving mail and to stop using it. And those people will do the same with their people. I think that's why it's important for people to keep at it with these "artisanal mail servers" (with the help of mail packages that do automatic configuration). More people can pressure Big Mail and demand that they let us deliver our (legit) mail as smoothly and easily as possible.

charcircuit 5y ago
They also need to have a reputation of being able to block spam.
- dqv 5y ago
  The issue is the spam still gets through on every single one of these providers, so that reputation isn’t nearly as important. Reliably receiving emails is. If that aspect of their reputation is damaged, it may never recover.

dheera 5y ago

Yes. I want to create a mail server that auto-rejects e-mail with externally hosted tracking pixels and returns a Mailer-Daemon error that tells the sender to re-send without malware. Of course with Gmail I disable automatic image loading to avoid being tracked, but I want to take a more active stance against the practice.

CogitoCogito 5y ago
What’s your method of detecting tracking pixels? Is it just as simple as scanning for size 1x1 images? I mean this as an honest question. I don’t really know variety of tracking pixels out there. Are there other similar things one should block?
- dheera 5y ago
  I would just block all images loaded from external URLs, since any of them could be used for tracking, but the newsletters are less my concern, it's more the individuals that I would be concerned about, and they tend to be a almost-fully plain text e-mail with a 1x1 image from one of many well-known domains for tracking.
  - sgarman 5y ago
    Since it's an email isn't every image from an external url? Do you just mean blocking all images?
    - collinmanderson 5y ago
      Emails can have "inline" attachments, where an image can be attached in the body of the email itself. So the image shows up without any network access, but it's generally base-64 encoded (costing 4x space) and ends up using a lot of email storage space.
      - sfoley 5y ago
        Base64 costs 1.3x space, not 4x.

micromacrofoot 5y ago

unfortunately as long as you’re sending email to other people you’re subject to Google’s filtering rules, so it may be easier to work with a provider that operates at a scale google cares about… it’s all a racket if you ask me… their algo can doom any individual self-hoster to perpetual spam hell and they’ve got zero service

deleted 5y ago

[deleted]