6 ms·

Tutorials for setting up a personal email server are fine for educational purposes -- or -- if you're primarily using it to receive emails. On the other hand,

by jasode 9y ago

Tutorials for setting up a personal email server are fine for educational purposes -- or -- if you're primarily using it to receive emails. On the other hand, if you absolutely depend on the ability to send emails such that your recipients reliably get them, hosting your own email server is extremely tricky. One could carefully go through the checklist of SPF, DKIM, ip blacklists, etc and emails will still be rejected by MS Hotmail, GMail, Yahoo, etc. Those giants are "black boxes" when it comes to their heuristics for rejecting incoming mail as spam. E.g. your hosted email server does nothing wrong but some other bad actor on your ip block sends spam which then makes MS/Google block you because of "guilty by association". Trying to debug your "sender reputation" is not easy. In the 1990s, I hosted my own home email server over ISDN lines. These days, I have a million other things I'd rather do than babysit a personal email server with software updates, SpamAssassin lists, etc. I get the whole decentralized ethos but it's just not worth the effort for email servers.

tjoff 9y ago
What kind of colossal idiot would block an email because it comes from a certain IP-block IF SPF and DKIM has been properly setup? Is this an urban legend that just keeps getting repeated?
- jdietrich 9y ago
  Statistically, a random mailserver on a random IP address is overwhelmingly likely to be sending spam. All the large mail providers use Bayesian filtering and are willing to tolerate a modest false-positive rate to ensure a low false-negative rate. A spam blocklist is not a court of law. As far as the mail providers are concerned, you're guilty until proven innocent. SPF and DKIM are no guarantee that you're not a spammer.
- interfixus 9y ago
  No, it's real. I gave it up a year ago, after hosting my own mail since forever. Exactly as stated: Hotmail (or whatever MS mail is called these days), GMail etc. are the main culprits. So yes, 'colossal' is the word.
  - danieltillett 9y ago
    Yep I did the same. I ran my own email server off the same IP address for 15 years with zero problems, but I had to give up recently because email is not something that you can do on you own anymore. You now have to pay some somebody to vouch for you or else MS will send your emails to spam or even worse just randomly delete them.
    - EGreg 9y ago
      Something should eventually come along and replace email. Like bitcoin and other technologies, what was originally designed to be decentralized became centralized in practice.
      - mbrock 9y ago
        Bitcoin's history involves a plan for combating spam—that's why proof of work was invented. Hashcash, Bitcoin's PoW game, was intended for use as an email attachment to create a real cost to spam without any micropayments. "If you want to mail me, prove that you burned five seconds of CPU time."
        kuczmama 9y ago
        That is really interesting. Do you know of any articles that go into more details?
    - reitanqild 9y ago
      Could be you had a customer/other recipient like my ex-boss: I'm fairly certain he used the spam button instead of delete on his Google apps for your domain (now gsuite I guess) account.
  - gamache 9y ago
    Hosted my own email for 18 years, same experience, switched to pobox.com about two years ago. It really burns me up, but I need my emails to arrive where I sent them.
- colejohnson66 9y ago
  > E.g. your hosted email server does nothing wrong but some other bad actor on your ip block sends spam which then makes MS/Google block you because of "guilty by association". That’s why
  - tjoff 9y ago
    No. That is not why, the reason must be something else. The only explanation that makes sense is deliberate sabotage to eradicate competition. But I'm not suggesting that, it is just that I can not think of any other reason. What is the motivation for the "guilty by association"? Because you can not verify who sent it. With SPF and DKIM you can - that is the whole point, you know beyond any doubt that the machine supposed to send that mail actually did send it. Now, if the person behind that machine is a spammer (or has been hijacked by a spammer) and sends out a lot of spam (and gets reported as such) then just nuke that sender. It is dead easy to do regardless of what IP it was sent from - each mail have identification credentials built in. It could not get any easier to do. The sender did all of the work for you by going through the extra effort of identifying itself.
    - DanBC 9y ago
      > What is the motivation for the "guilty by association"? One that has been given in the past is "Stop paying money to companies that host spammer websites and spammer email servers, or we'll block your email too" (I don't particularly agree with it, but it was common to see that argument on news.admin.net-abuse.email
    - jazoom 9y ago
      Exactly. I also find this ridiculous.
    - bradknowles 9y ago
      Yeah, but they don’t identify themselves correctly. They lie. Sometimes they claim to be real people with real e-mail addresses that they don’t actually own, and maybe that real person is you — in which case it is your reputation that gets permanently dinged. Sometimes they claim to be fake people with fake e-mail addresses that don’t actually exist, in which case all you really know is the IP address they used to send the message. When they do this, they frequently arrange to get a large block of IP addresses they can use, and then cycle through them very quickly — maybe no more than five minutes per IP address. Anyone else who happens to be in that same range now gets their reputation dinged by association. There’s a lot of tricks spammers use to try to hide their activity. And lots of ways to try to detect and reject that on the other end. It’s a never-ending arms race, and on the Internet it is easy to hide and hard to take out miscreants without causing excessive collateral damage. And many big providers don’t care if they cause collateral damage.
- nasalgoat 9y ago
  My company's email server ends up on RBLs once in a while due to such nonsense, and I have a perfect SPL and DMARC score.
- DanBC 9y ago
  > What kind of colossal idiot would block an email because it comes from a certain IP-block IF SPF and DKIM has been properly setup? I don't know if anything like SPEWS is still around but they used to do large blocks. I still don't know if it was genuine attempt to reduce spam, or performance art, or god-tier trolling. https://en.wikipedia.org/wiki/Spam_Prevention_Early_Warning_System https://en.wikipedia.org/wiki/Spam_Prevention_Early_Warning_... https://web-beta.archive.org/web/20030609200813/http://www.spews.org/ https://web-beta.archive.org/web/20030609200813/http://www.s...
- KyeRussell 9y ago
  No, in my extremely limited experience with email deliverability, this happens. I'd imagine a person that actually does this stuff day-to-day sees it a lot more than I do. You can do "everything right" rolling your own email, but you are still relying on the receiving parties to do their job and implement sane spam prevention policies. This is far from what actually happens. I lead development on a project that sends a lot of (legitimate, user-requested, transactional) email to many mailboxes belonging to a certain government department. I used Amazon SES as they have a pretty good track record. The receiving mail servers were configured to use a few overzealous blacklists that were causing my email to be silently swallowed (and reported as delivered). This was based on an IP black-level ban. Simply Googling the names of these blacklists showed report after report after report of them being completely useless, with many seasoned sysadmins saying that nobody worth their salt should pay any attention to them. This was extremely hard to troubleshoot as this department was not a direct client and was of limited helpfulness. It became apparent that using SES's newly-launched dedicated IP functionality wouldn't have helped. I made full use of my AWS Business Support, the multiple people I talked to made it clear that SES put a great deal of effort into ensuring their IP ranges are "clean" - but there are some spam lists that do not play ball. The most important takeaway was that I was doing everything right. I was using a reputable mail provider who have very stringent spam prevention controls. I utilised SPF and DKIM. The content of my mail shouldn't have (and didn't) trigger a content-based spam detector. It was because the people on the other side weren't doing their job to an acceptable standard. When I was eventually able to open a channel of contact with the receiving department, they confirmed it was an IP range-based ban. The fact that I was doing everything in my power to do the right thing had no effect on the situation. I still wasn't getting mail to customers. Saying "darm, these sysadmins really aren't doing their job properly!" had no effect on the situation at all. We still live in the age of almost-but-not-quite-plug-and-play email solutions like Exchange that can be configured by people that probably shouldn't be configuring mail servers. For all I know, there was a list of blacklists on some Hosted Outlook control panel and the person in charge ticked all of them because more is better. As long as this is the reality I live in, I'm going to do all I can to play ball and succumb to the black magic. I can imagine my experience would've been a lot worse if I had been operating a mail server out of a dirtier IP range (generic cloud hosting provider, retail ISP customer IP range.etc). If I recall correctly, AWS severely limits sending mail from EC2 instances because they don't want their IP addresses / IP ranges to end up on mail blacklists.
- dboreham 9y ago
  There are more collosal idiots around than you allow for. Also, it isn't in said idiot's interest to deliver your email properly. They would rather fart around with machine learning and blame whatever happens on incomplete training data...
Neil44 9y ago
MS actually have a service where you can register IP’s you own and it gives you a digest of what people have marked as spam that originated from said IP’s. Their headers also tell you a lot, excepting the content filter one which is a bit of a black box and I don’t believe actually is purely a content filter based on messing with it. (Responding to black box comment)
- blfr 9y ago
  Smart Network Data Service[1] which, like Google's postmaster[2], is not terribly useful for small servers as it requires a certain volume of messages before it shows any info. A volume you won't reach from a personal server. [1] https://postmaster.live.com/snds/ https://postmaster.live.com/snds/ [2] https://postmaster.google.com/ https://postmaster.google.com/
lucb1e 9y ago
I don't have time to reply at length on a touchscreen but this topic comes up every time someone links "how to self-host email". Saying it's extremely tricky is exaggerating. Everyone agrees it takes more work than it does to create a gmail account, but it's not that hard either. I don't think we should dissuade people from doing it, especially if the fact that more people doing it means that it'll be easier next time because it'll be slightly more common. Many of us are in tech and the field is a small subset of the population. Even if it's a small amount of servers setup by us, that could make a noticeable on those working at bigcorps who write the hostile receivers.
- supermatt 9y ago
  I dont think you understand what GP is saying. Setting up is easy, maintaining and responding to all the blocks you may get is ongoing and simply cumbersome. That is what people are referring to when they say its tricky. You may wake up one morning, and find your host is blocked through association (if you are lucky - some hosts will simply silently swallow your mail - i.e. it never arrives and you dont know about it). You can apply for removal in some cases (and wait for it to update before you resend), and in other cases find your hosts entire subnet is blocked, resulting in you having to set up another server on a different subnet in order to relay your email. There are ways around a lot of this, but hosting on AWS/DO/Etc not having your own assigned subnet, etc, will most definitely result in the above when you least want it to happen. Of course SPF and DKIM were supposed to alleviate the need for these IP based blocks, but the reality is that they haven't changed a thing when it comes to sending email to large hosts. Thats why we say its tricky.
  - lucb1e 9y ago
    > Setting up is easy, maintaining and responding to all the blocks you may get is ongoing and simply cumbersome. The only real issues I had were with Gmail for a few months, until they got used to the IP address sending legit email. You have to instruct people to look in their spam folder (of which Gmail hides the existence, an evil thing in itself) until people marked like 10 emails as being non-spam over the course of a few months. Hardly had any trouble otherwise, and I don't even use DKIM nor a reverse DNS for all domains (only SPF because that was easy to do, and with 1 IP address I can do only 1 reverse DNS, and only v4 at that). It helps that I've got a static address, and it might also help that XS4ALL (ISP) has a good abuse team that probably keeps the netblock quite clean. I don't know to what degree this affected my experience.
dk28 9y ago
do you work for NSA?
insertnickname 9y ago
I've been hosting my own personal mail server for about a year. Had to go through some arcane process to be "allowed" to send mails to Hotmail and my mails have been marked as spam once or twice by Gmail, but I don't usually have problems with delivery. Running your own mail server does require investing some time in learning the software, the protocols and all the ways spam filters will sabotage your attempts to send legitimate, non-bulk e-mail, as well as a little time for maintenance, but it's really not as bad as people say, at least in my experience. It's not something you "just" do, but it is doable.
- cariaso 9y ago
  Could you share info about the arcane process with me ( cariaso@gmail.com ) . I manage delivery to most sites with no issue, but hotmail nearly always ends up in spam, and I'd love to try and address this.
  - ryan-c 9y ago
    There's some information here - they don't link all the tools mentioned, but it'll give you the terms to search for: https://mail.live.com/mail/services.aspx https://mail.live.com/mail/services.aspx
  - insertnickname 9y ago
    Sent you an e-mail. Hopefully Gmail doesn't chuck it!
- kuczmama 9y ago
  I would also like to know about the this. If you wouldn't mind letting me know some of the things you did that could be really helpful
  - insertnickname 9y ago
    I used the process described in this blog post to be able to deliver to Hotmail: https://blog.stickleback.dk/getting-off-hotmails-blocklist/ https://blog.stickleback.dk/getting-off-hotmails-blocklist/ (not my blog). I got the same strange automated responses as this guy got, but I got off their blacklist after a couple of hours. More generally: - I made sure my server's IP addresses weren't on any blacklists. - I host my mail server with a reputable hosting provider (RamNode). Stay clear of companies like OVH that have reputations for poor abuse handling. - I have configured SPF, DKIM, and DMARC. - I registered my server with https://www.dnswl.org/ https://www.dnswl.org/, a whitelist for legitimate mail servers. - I don't send spam or other bulk e-mail, only personal correspondence. I also tried sending e-mails to a couple of people I know who use Gmail. I asked them to mark my mails as 'not spam' if they went into their junk folders. I don't know how much this helps "globally" in the Gmail system, but at least it'll teach Gmail not to mark my mails as spam for those people. I had used my current personal domain for e-mail for a couple of years but I paid a company to host my e-mail for me. It might have helped that my domain had already built up a good reputation in big mail companies' spam filters, but who knows... It definitely helps, however, that my domain wasn't brand new. Newly registered domains are often penalized by spam filters. A poor choice of TLD can also hurt delivery: I know that many mail admins penalize or out-right block many of the new gTLDs like .top and .download. I am not discounting those who complain about deliverability, but so far I haven't had much trouble with my low-volume, personal mail server.
eric_h 9y ago
I used to (in the early 00's) manage email servers for a small company that among other things did web and email hosting for other small companies. It was annoying as hell and I will never do it again, I no longer have the patience for it.
SudoAlex 9y ago
Or you do nothing wrong on your server, but another user using your mail server ends up with a compromised password, or reuses the same username/password from elsewhere as their mail login. You wake up and see thousands of outgoing emails in your mail queue, all from the spammer, followed by other users who can't send outgoing emails. You could attempt to limit the outgoing emails per account per hour, however if that's set too low then you end up with other users who can't send out emails to their "mailing lists" consisting of hundreds of contacts, instead of using a real mailing list to manage it. The effort just isn't worth it.

by jasode 9y ago

tjoff 9y ago

What kind of colossal idiot would block an email because it comes from a certain IP-block IF SPF and DKIM has been properly setup? Is this an urban legend that just keeps getting repeated?

jdietrich 9y ago
Statistically, a random mailserver on a random IP address is overwhelmingly likely to be sending spam. All the large mail providers use Bayesian filtering and are willing to tolerate a modest false-positive rate to ensure a low false-negative rate. A spam blocklist is not a court of law. As far as the mail providers are concerned, you're guilty until proven innocent. SPF and DKIM are no guarantee that you're not a spammer.
interfixus 9y ago
No, it's real. I gave it up a year ago, after hosting my own mail since forever. Exactly as stated: Hotmail (or whatever MS mail is called these days), GMail etc. are the main culprits. So yes, 'colossal' is the word.
- danieltillett 9y ago
  Yep I did the same. I ran my own email server off the same IP address for 15 years with zero problems, but I had to give up recently because email is not something that you can do on you own anymore. You now have to pay some somebody to vouch for you or else MS will send your emails to spam or even worse just randomly delete them.
  - EGreg 9y ago
    Something should eventually come along and replace email. Like bitcoin and other technologies, what was originally designed to be decentralized became centralized in practice.
    - mbrock 9y ago
      Bitcoin's history involves a plan for combating spam—that's why proof of work was invented. Hashcash, Bitcoin's PoW game, was intended for use as an email attachment to create a real cost to spam without any micropayments. "If you want to mail me, prove that you burned five seconds of CPU time."
      - kuczmama 9y ago
        That is really interesting. Do you know of any articles that go into more details?
  - reitanqild 9y ago
    Could be you had a customer/other recipient like my ex-boss: I'm fairly certain he used the spam button instead of delete on his Google apps for your domain (now gsuite I guess) account.
- gamache 9y ago
  Hosted my own email for 18 years, same experience, switched to pobox.com about two years ago. It really burns me up, but I need my emails to arrive where I sent them.
colejohnson66 9y ago
> E.g. your hosted email server does nothing wrong but some other bad actor on your ip block sends spam which then makes MS/Google block you because of "guilty by association". That’s why
- tjoff 9y ago
  No. That is not why, the reason must be something else. The only explanation that makes sense is deliberate sabotage to eradicate competition. But I'm not suggesting that, it is just that I can not think of any other reason. What is the motivation for the "guilty by association"? Because you can not verify who sent it. With SPF and DKIM you can - that is the whole point, you know beyond any doubt that the machine supposed to send that mail actually did send it. Now, if the person behind that machine is a spammer (or has been hijacked by a spammer) and sends out a lot of spam (and gets reported as such) then just nuke that sender. It is dead easy to do regardless of what IP it was sent from - each mail have identification credentials built in. It could not get any easier to do. The sender did all of the work for you by going through the extra effort of identifying itself.
  - DanBC 9y ago
    > What is the motivation for the "guilty by association"? One that has been given in the past is "Stop paying money to companies that host spammer websites and spammer email servers, or we'll block your email too" (I don't particularly agree with it, but it was common to see that argument on news.admin.net-abuse.email
  - jazoom 9y ago
    Exactly. I also find this ridiculous.
  - bradknowles 9y ago
    Yeah, but they don’t identify themselves correctly. They lie. Sometimes they claim to be real people with real e-mail addresses that they don’t actually own, and maybe that real person is you — in which case it is your reputation that gets permanently dinged. Sometimes they claim to be fake people with fake e-mail addresses that don’t actually exist, in which case all you really know is the IP address they used to send the message. When they do this, they frequently arrange to get a large block of IP addresses they can use, and then cycle through them very quickly — maybe no more than five minutes per IP address. Anyone else who happens to be in that same range now gets their reputation dinged by association. There’s a lot of tricks spammers use to try to hide their activity. And lots of ways to try to detect and reject that on the other end. It’s a never-ending arms race, and on the Internet it is easy to hide and hard to take out miscreants without causing excessive collateral damage. And many big providers don’t care if they cause collateral damage.
nasalgoat 9y ago
My company's email server ends up on RBLs once in a while due to such nonsense, and I have a perfect SPL and DMARC score.
DanBC 9y ago
> What kind of colossal idiot would block an email because it comes from a certain IP-block IF SPF and DKIM has been properly setup? I don't know if anything like SPEWS is still around but they used to do large blocks. I still don't know if it was genuine attempt to reduce spam, or performance art, or god-tier trolling. https://en.wikipedia.org/wiki/Spam_Prevention_Early_Warning_System https://en.wikipedia.org/wiki/Spam_Prevention_Early_Warning_... https://web-beta.archive.org/web/20030609200813/http://www.spews.org/ https://web-beta.archive.org/web/20030609200813/http://www.s...
KyeRussell 9y ago
No, in my extremely limited experience with email deliverability, this happens. I'd imagine a person that actually does this stuff day-to-day sees it a lot more than I do. You can do "everything right" rolling your own email, but you are still relying on the receiving parties to do their job and implement sane spam prevention policies. This is far from what actually happens. I lead development on a project that sends a lot of (legitimate, user-requested, transactional) email to many mailboxes belonging to a certain government department. I used Amazon SES as they have a pretty good track record. The receiving mail servers were configured to use a few overzealous blacklists that were causing my email to be silently swallowed (and reported as delivered). This was based on an IP black-level ban. Simply Googling the names of these blacklists showed report after report after report of them being completely useless, with many seasoned sysadmins saying that nobody worth their salt should pay any attention to them. This was extremely hard to troubleshoot as this department was not a direct client and was of limited helpfulness. It became apparent that using SES's newly-launched dedicated IP functionality wouldn't have helped. I made full use of my AWS Business Support, the multiple people I talked to made it clear that SES put a great deal of effort into ensuring their IP ranges are "clean" - but there are some spam lists that do not play ball. The most important takeaway was that I was doing everything right. I was using a reputable mail provider who have very stringent spam prevention controls. I utilised SPF and DKIM. The content of my mail shouldn't have (and didn't) trigger a content-based spam detector. It was because the people on the other side weren't doing their job to an acceptable standard. When I was eventually able to open a channel of contact with the receiving department, they confirmed it was an IP range-based ban. The fact that I was doing everything in my power to do the right thing had no effect on the situation. I still wasn't getting mail to customers. Saying "darm, these sysadmins really aren't doing their job properly!" had no effect on the situation at all. We still live in the age of almost-but-not-quite-plug-and-play email solutions like Exchange that can be configured by people that probably shouldn't be configuring mail servers. For all I know, there was a list of blacklists on some Hosted Outlook control panel and the person in charge ticked all of them because more is better. As long as this is the reality I live in, I'm going to do all I can to play ball and succumb to the black magic. I can imagine my experience would've been a lot worse if I had been operating a mail server out of a dirtier IP range (generic cloud hosting provider, retail ISP customer IP range.etc). If I recall correctly, AWS severely limits sending mail from EC2 instances because they don't want their IP addresses / IP ranges to end up on mail blacklists.
dboreham 9y ago
There are more collosal idiots around than you allow for. Also, it isn't in said idiot's interest to deliver your email properly. They would rather fart around with machine learning and blame whatever happens on incomplete training data...

Neil44 9y ago

MS actually have a service where you can register IP’s you own and it gives you a digest of what people have marked as spam that originated from said IP’s. Their headers also tell you a lot, excepting the content filter one which is a bit of a black box and I don’t believe actually is purely a content filter based on messing with it. (Responding to black box comment)

blfr 9y ago
Smart Network Data Service[1] which, like Google's postmaster[2], is not terribly useful for small servers as it requires a certain volume of messages before it shows any info. A volume you won't reach from a personal server. [1] https://postmaster.live.com/snds/ https://postmaster.live.com/snds/ [2] https://postmaster.google.com/ https://postmaster.google.com/

lucb1e 9y ago

I don't have time to reply at length on a touchscreen but this topic comes up every time someone links "how to self-host email". Saying it's extremely tricky is exaggerating. Everyone agrees it takes more work than it does to create a gmail account, but it's not that hard either. I don't think we should dissuade people from doing it, especially if the fact that more people doing it means that it'll be easier next time because it'll be slightly more common. Many of us are in tech and the field is a small subset of the population. Even if it's a small amount of servers setup by us, that could make a noticeable on those working at bigcorps who write the hostile receivers.

supermatt 9y ago
I dont think you understand what GP is saying. Setting up is easy, maintaining and responding to all the blocks you may get is ongoing and simply cumbersome. That is what people are referring to when they say its tricky. You may wake up one morning, and find your host is blocked through association (if you are lucky - some hosts will simply silently swallow your mail - i.e. it never arrives and you dont know about it). You can apply for removal in some cases (and wait for it to update before you resend), and in other cases find your hosts entire subnet is blocked, resulting in you having to set up another server on a different subnet in order to relay your email. There are ways around a lot of this, but hosting on AWS/DO/Etc not having your own assigned subnet, etc, will most definitely result in the above when you least want it to happen. Of course SPF and DKIM were supposed to alleviate the need for these IP based blocks, but the reality is that they haven't changed a thing when it comes to sending email to large hosts. Thats why we say its tricky.
- lucb1e 9y ago
  > Setting up is easy, maintaining and responding to all the blocks you may get is ongoing and simply cumbersome. The only real issues I had were with Gmail for a few months, until they got used to the IP address sending legit email. You have to instruct people to look in their spam folder (of which Gmail hides the existence, an evil thing in itself) until people marked like 10 emails as being non-spam over the course of a few months. Hardly had any trouble otherwise, and I don't even use DKIM nor a reverse DNS for all domains (only SPF because that was easy to do, and with 1 IP address I can do only 1 reverse DNS, and only v4 at that). It helps that I've got a static address, and it might also help that XS4ALL (ISP) has a good abuse team that probably keeps the netblock quite clean. I don't know to what degree this affected my experience.

dk28 9y ago

do you work for NSA?

insertnickname 9y ago

I've been hosting my own personal mail server for about a year. Had to go through some arcane process to be "allowed" to send mails to Hotmail and my mails have been marked as spam once or twice by Gmail, but I don't usually have problems with delivery. Running your own mail server does require investing some time in learning the software, the protocols and all the ways spam filters will sabotage your attempts to send legitimate, non-bulk e-mail, as well as a little time for maintenance, but it's really not as bad as people say, at least in my experience. It's not something you "just" do, but it is doable.

cariaso 9y ago
Could you share info about the arcane process with me ( cariaso@gmail.com ) . I manage delivery to most sites with no issue, but hotmail nearly always ends up in spam, and I'd love to try and address this.
- ryan-c 9y ago
  There's some information here - they don't link all the tools mentioned, but it'll give you the terms to search for: https://mail.live.com/mail/services.aspx https://mail.live.com/mail/services.aspx
- insertnickname 9y ago
  Sent you an e-mail. Hopefully Gmail doesn't chuck it!
kuczmama 9y ago
I would also like to know about the this. If you wouldn't mind letting me know some of the things you did that could be really helpful
- insertnickname 9y ago
  I used the process described in this blog post to be able to deliver to Hotmail: https://blog.stickleback.dk/getting-off-hotmails-blocklist/ https://blog.stickleback.dk/getting-off-hotmails-blocklist/ (not my blog). I got the same strange automated responses as this guy got, but I got off their blacklist after a couple of hours. More generally: - I made sure my server's IP addresses weren't on any blacklists. - I host my mail server with a reputable hosting provider (RamNode). Stay clear of companies like OVH that have reputations for poor abuse handling. - I have configured SPF, DKIM, and DMARC. - I registered my server with https://www.dnswl.org/ https://www.dnswl.org/, a whitelist for legitimate mail servers. - I don't send spam or other bulk e-mail, only personal correspondence. I also tried sending e-mails to a couple of people I know who use Gmail. I asked them to mark my mails as 'not spam' if they went into their junk folders. I don't know how much this helps "globally" in the Gmail system, but at least it'll teach Gmail not to mark my mails as spam for those people. I had used my current personal domain for e-mail for a couple of years but I paid a company to host my e-mail for me. It might have helped that my domain had already built up a good reputation in big mail companies' spam filters, but who knows... It definitely helps, however, that my domain wasn't brand new. Newly registered domains are often penalized by spam filters. A poor choice of TLD can also hurt delivery: I know that many mail admins penalize or out-right block many of the new gTLDs like .top and .download. I am not discounting those who complain about deliverability, but so far I haven't had much trouble with my low-volume, personal mail server.

eric_h 9y ago

I used to (in the early 00's) manage email servers for a small company that among other things did web and email hosting for other small companies. It was annoying as hell and I will never do it again, I no longer have the patience for it.

SudoAlex 9y ago

Or you do nothing wrong on your server, but another user using your mail server ends up with a compromised password, or reuses the same username/password from elsewhere as their mail login. You wake up and see thousands of outgoing emails in your mail queue, all from the spammer, followed by other users who can't send outgoing emails. You could attempt to limit the outgoing emails per account per hour, however if that's set too low then you end up with other users who can't send out emails to their "mailing lists" consisting of hundreds of contacts, instead of using a real mailing list to manage it. The effort just isn't worth it.