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> I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being mar

> I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being marked as spam Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it. In fact, I used to think exactly like you when I originally set up my personal mail server and opted for the hybrid setup you suggest. However, when the third party service I used to send mail shut down a couple of years ago, I quiclky set up outbound mail on my own server. None of my emails are considered as spam, and I haven't touched the mail configuration since.

defanor 7y ago
Not GP, but it matches my experience: with reverse DNS, DKIM, SPF, being in DNSWL (and not in DNSBLs) some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance). A while ago there were strange issues with Google-hosted mailing lists as well, with some messages not being visible even to an ML administrator, while Gmail servers accepted mail just fine (maybe it still happens, I'm just not writing to those). I hear similar stories from other mail server administrators too. I think it's more of a Gmail/BigMailerCorp issue, and still using a private mail server myself, but I don't think it's fair to say that it's all easy and works flawlessly, even with strangely behaving mail servers on the other end.
- pw6hv 7y ago
  > some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance) How did this happen if Gmail deletes spam after some weeks?
  - defanor 7y ago
    Indeed, a quick search suggests that spam is automatically removed every 30 days there. The wording was "Google hid it from me", so either I have wrongly assumed that it's about the spam folder, or it is possible to disable autoremoval. Edit: or, as the sibling comment suggests, it behaves strangely with respect to removal as well.
    - scarejunba 7y ago
      Or user accidentally archived it. “X did Y” is often a user’s way of saying “I accidentally made X do Y” without having to accept blame. It’s the “dog ate my homework” of excuses.
    - inetknght 7y ago
      Another instance of Google being user hostile?
  - RandomBacon 7y ago
    I recently checked my Trash folder in Gmail. I had emails in there that were several years old, right below the text that says Gmail deletes emails in the Trash folder older than 30 days.
toomim 7y ago
I think that because I tried it and my outgoing emails weren't being delivered. Big mail companies have blacklisted entire C-blocks of IP addresses at VPS providers, because parts of those blocks have been used to send spam in the past, and you won't know until you actually check with people you are sending mail to, to ask if they've received them. It sucks.
- u801e 7y ago
  Wouldn't the mail server log the connection attempt and the rejection reason?
eikenberry 7y ago
> Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it. Not sure about OP, but many people have tried it and it is a PITA. Even once you have everything setup right (SPF, DKIM, etc.), you still have to deal with IP issues. I ran my own mail server for years (actually, still do for incoming) and it worked fine for about 10 years until I needed to switch providers and got a new IP. Then I found I had to deal with an IP with no reputation and IP whitelist/blacklists. The deal breaker was finally dealing with blacklists that you had to pay to keep off of. UCEPROTECT was the one at the time. They would randomly add my provider's entire IP space to one of their lists and during those times all email to a couple ISPs would bounce and the only way to get my IP whitelisted from those blanket bans was to pay $$. Switched to using an external provider for outgoing mail and haven't had a problem since as they take care of that crap.
- al_form2000 7y ago
  UCEPROTECT was the pits and its operators were unprincipled lowlifes. Luckily they (like all the pay-to-delist BLs) never got more than minimal traction, so ignoring them and their BS mostly worked ('course you needed a /19 to be effective at doing that)
  - eikenberry 7y ago
    You use past tense... why? They still exist and seem to be continuing their blacklist/blackmail BS. The ISP in question was AT&T and their subsidiaries (I mostly got hit sending to bellsouth.net), which I wouldn't consider to be that small of an ISP and was enough that I eventually gave up.
    - al_form2000 7y ago
      Past (more than 5 years ago as I reckon) is when I locked horns with them. They may have switched policies, I may have gotten smarter than them, who knows.
      - 7y ago
uijdihrihr 7y ago
I work in the industry and it's no myth. Even using expensive relay servers doesn't guarantee the big email providers will deliver your or mail or care much to explain why it isn't being delivered. Big email won't even respond to their own customer complaints that they aren't receiving email.
baobabKoodaa 7y ago
> None of my emails are considered as spam, and I haven't touched the mail configuration since. Sounds like you never actually tried to measure the delivery rates of your outgoing email. No email server is actually able to get 100% of its outgoing mail past spam filters. I've ran my own email server for a few years and I can confirm that the article is making false claims. It's incredibly difficult to deliver email as a low volume sender. The article falsely claims that it's not difficult and that people simply haven't tried it. Well guess what, I did try it - for years - with countless hours sank into it. I wrote a blog post documenting my numerous, unsuccessful efforts to get my email delivered. I wish people would stop spreading these baseless falsehoods. https://www.attejuvonen.fi/dont-send-email-from-your-own-server/ https://www.attejuvonen.fi/dont-send-email-from-your-own-ser...
- com2kid 7y ago
  Gmail occasionally classifies the random email from YouTube as spam. Given that, 100% delivery rate seems like a dream.
- djsumdog 7y ago
  I've written a similar article: https://penguindreams.org/blog/how-google-and-microsoft-made-email-unreliable/ https://penguindreams.org/blog/how-google-and-microsoft-made...
dpifke 7y ago
New domains and new IPs are penalized heavily by most services' spam filters. My guess is that a lot of people try it, have poor delivery rates, and abandon the effort before they have enough time to develop decent domain & IP reputations. I've been running my own personal mail servers since 1995, on my current IP addresses since ~2016. If I add a new domain to my configuration, it takes 1-2 weeks before Gmail will reliably accept mail from it. Once I wait that out, delivery is mostly flawless.
jojoo 7y ago
I've been running a mailserver for ~15 Years. I found it to be very time consuming and complicated, mainly because of the trouble of outgoing mail.
juped 7y ago
No - the article contradicts itself. The author says it's "a myth" and "just set up spf/dkim", and then later says "This is already happening with one specifically requiring mails to be sent from another Big Mailer Corp to hit the inbox, or requiring that senders be added to the contacts for others. Any other sender will hit spambox unconditionnally for a while before being eventually upgraded to inbox." Which is it? Those of us who have run mail servers know that you get unconditionally spammed all the time.
rstuart4133 7y ago
As a person who does run a number of (smallish) mail servers, some outgoing mail does get classified as SPAM and I have to fix it. It's very rare - every 3 months or so maybe, but it does happen. (Possibly the most irritating thing about this is they won't tell you what emails made them think you are sending spam, lets alone why they thing it's spam which makes root cause analysis damned near impossible.) The reverse happens too - we occasionally block non-spam emails. But, and it's a damned big but, AFAICT, my email servers make less of those mistakes than the big email providers like Google or Microsoft, so the overall reliability of my home grow system is higher. It's got to the point that when someone complains they didn't get an email I got, my first question is "do you use gmail?". The other big but it is it complex. It isn't just a single server - they are a network of them that distribute email across a geographically dispersed organisation. Despite being distributed it archives copies of all email that passes through it (as required by law here). There are some 2.5K of configuration lines driving it. So yes, it requires some effort to set it up. However, like your case those 2.5K lines haven't changed overly in over a decade. The flexibility the system provides us in the way we handle email is invaluable. As a consequence of that flexibility a lot of emails are never seen by humans - they routed to a place they can be automatically processed. Personally I wouldn't say email particularly hard, or particularly easy. It seems no more difficult than all the other things you have to do to manage a cluster of servers. The rewards for getting do it inhouse are pretty big, because just like everything else a programmer or sysadmin has control of, over time it will be scripted so heavily it will become almost invisible.
marticode 7y ago
I tried it a couple years ago. Delivering to large providers wasn't the problem. The problem was smaller ISP, one of them flat-out banned all IPs from my host provider (Digital Ocean), others for no reason I could find banned my specific IP. (I was not on any public block list BTW) Getting off their block list was either impossible or involved digging some old forum posts to find an email address that you could try your luck with, usually with no result as it seems nobody was reading it anyway.

defanor 7y ago

Not GP, but it matches my experience: with reverse DNS, DKIM, SPF, being in DNSWL (and not in DNSBLs) some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance). A while ago there were strange issues with Google-hosted mailing lists as well, with some messages not being visible even to an ML administrator, while Gmail servers accepted mail just fine (maybe it still happens, I'm just not writing to those). I hear similar stories from other mail server administrators too. I think it's more of a Gmail/BigMailerCorp issue, and still using a private mail server myself, but I don't think it's fair to say that it's all easy and works flawlessly, even with strangely behaving mail servers on the other end.

pw6hv 7y ago
> some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance) How did this happen if Gmail deletes spam after some weeks?
- defanor 7y ago
  Indeed, a quick search suggests that spam is automatically removed every 30 days there. The wording was "Google hid it from me", so either I have wrongly assumed that it's about the spam folder, or it is possible to disable autoremoval. Edit: or, as the sibling comment suggests, it behaves strangely with respect to removal as well.
  - scarejunba 7y ago
    Or user accidentally archived it. “X did Y” is often a user’s way of saying “I accidentally made X do Y” without having to accept blame. It’s the “dog ate my homework” of excuses.
  - inetknght 7y ago
    Another instance of Google being user hostile?
- RandomBacon 7y ago
  I recently checked my Trash folder in Gmail. I had emails in there that were several years old, right below the text that says Gmail deletes emails in the Trash folder older than 30 days.

toomim 7y ago

I think that because I tried it and my outgoing emails weren't being delivered. Big mail companies have blacklisted entire C-blocks of IP addresses at VPS providers, because parts of those blocks have been used to send spam in the past, and you won't know until you actually check with people you are sending mail to, to ask if they've received them. It sucks.

u801e 7y ago
Wouldn't the mail server log the connection attempt and the rejection reason?

eikenberry 7y ago

> Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it. Not sure about OP, but many people have tried it and it is a PITA. Even once you have everything setup right (SPF, DKIM, etc.), you still have to deal with IP issues. I ran my own mail server for years (actually, still do for incoming) and it worked fine for about 10 years until I needed to switch providers and got a new IP. Then I found I had to deal with an IP with no reputation and IP whitelist/blacklists. The deal breaker was finally dealing with blacklists that you had to pay to keep off of. UCEPROTECT was the one at the time. They would randomly add my provider's entire IP space to one of their lists and during those times all email to a couple ISPs would bounce and the only way to get my IP whitelisted from those blanket bans was to pay $$. Switched to using an external provider for outgoing mail and haven't had a problem since as they take care of that crap.

al_form2000 7y ago
UCEPROTECT was the pits and its operators were unprincipled lowlifes. Luckily they (like all the pay-to-delist BLs) never got more than minimal traction, so ignoring them and their BS mostly worked ('course you needed a /19 to be effective at doing that)
- eikenberry 7y ago
  You use past tense... why? They still exist and seem to be continuing their blacklist/blackmail BS. The ISP in question was AT&T and their subsidiaries (I mostly got hit sending to bellsouth.net), which I wouldn't consider to be that small of an ISP and was enough that I eventually gave up.
  - al_form2000 7y ago
    Past (more than 5 years ago as I reckon) is when I locked horns with them. They may have switched policies, I may have gotten smarter than them, who knows.
    - 7y ago

uijdihrihr 7y ago

I work in the industry and it's no myth. Even using expensive relay servers doesn't guarantee the big email providers will deliver your or mail or care much to explain why it isn't being delivered. Big email won't even respond to their own customer complaints that they aren't receiving email.

baobabKoodaa 7y ago

> None of my emails are considered as spam, and I haven't touched the mail configuration since. Sounds like you never actually tried to measure the delivery rates of your outgoing email. No email server is actually able to get 100% of its outgoing mail past spam filters. I've ran my own email server for a few years and I can confirm that the article is making false claims. It's incredibly difficult to deliver email as a low volume sender. The article falsely claims that it's not difficult and that people simply haven't tried it. Well guess what, I did try it - for years - with countless hours sank into it. I wrote a blog post documenting my numerous, unsuccessful efforts to get my email delivered. I wish people would stop spreading these baseless falsehoods. https://www.attejuvonen.fi/dont-send-email-from-your-own-server/ https://www.attejuvonen.fi/dont-send-email-from-your-own-ser...

com2kid 7y ago
Gmail occasionally classifies the random email from YouTube as spam. Given that, 100% delivery rate seems like a dream.
djsumdog 7y ago
I've written a similar article: https://penguindreams.org/blog/how-google-and-microsoft-made-email-unreliable/ https://penguindreams.org/blog/how-google-and-microsoft-made...

dpifke 7y ago

New domains and new IPs are penalized heavily by most services' spam filters. My guess is that a lot of people try it, have poor delivery rates, and abandon the effort before they have enough time to develop decent domain & IP reputations. I've been running my own personal mail servers since 1995, on my current IP addresses since ~2016. If I add a new domain to my configuration, it takes 1-2 weeks before Gmail will reliably accept mail from it. Once I wait that out, delivery is mostly flawless.

jojoo 7y ago

I've been running a mailserver for ~15 Years. I found it to be very time consuming and complicated, mainly because of the trouble of outgoing mail.

juped 7y ago

No - the article contradicts itself. The author says it's "a myth" and "just set up spf/dkim", and then later says "This is already happening with one specifically requiring mails to be sent from another Big Mailer Corp to hit the inbox, or requiring that senders be added to the contacts for others. Any other sender will hit spambox unconditionnally for a while before being eventually upgraded to inbox." Which is it? Those of us who have run mail servers know that you get unconditionally spammed all the time.

rstuart4133 7y ago

As a person who does run a number of (smallish) mail servers, some outgoing mail does get classified as SPAM and I have to fix it. It's very rare - every 3 months or so maybe, but it does happen. (Possibly the most irritating thing about this is they won't tell you what emails made them think you are sending spam, lets alone why they thing it's spam which makes root cause analysis damned near impossible.) The reverse happens too - we occasionally block non-spam emails. But, and it's a damned big but, AFAICT, my email servers make less of those mistakes than the big email providers like Google or Microsoft, so the overall reliability of my home grow system is higher. It's got to the point that when someone complains they didn't get an email I got, my first question is "do you use gmail?". The other big but it is it complex. It isn't just a single server - they are a network of them that distribute email across a geographically dispersed organisation. Despite being distributed it archives copies of all email that passes through it (as required by law here). There are some 2.5K of configuration lines driving it. So yes, it requires some effort to set it up. However, like your case those 2.5K lines haven't changed overly in over a decade. The flexibility the system provides us in the way we handle email is invaluable. As a consequence of that flexibility a lot of emails are never seen by humans - they routed to a place they can be automatically processed. Personally I wouldn't say email particularly hard, or particularly easy. It seems no more difficult than all the other things you have to do to manage a cluster of servers. The rewards for getting do it inhouse are pretty big, because just like everything else a programmer or sysadmin has control of, over time it will be scripted so heavily it will become almost invisible.

marticode 7y ago

I tried it a couple years ago. Delivering to large providers wasn't the problem. The problem was smaller ISP, one of them flat-out banned all IPs from my host provider (Digital Ocean), others for no reason I could find banned my specific IP. (I was not on any public block list BTW) Getting off their block list was either impossible or involved digging some old forum posts to find an email address that you could try your luck with, usually with no result as it seems nobody was reading it anyway.