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I did run my own server with properly setup DKIM and SPF and all. Gmail and Hotmail would still mark my emails as spam whenever they felt like it. Sometimes,

I did run my own server with properly setup DKIM and SPF and all. Gmail and Hotmail would still mark my emails as spam whenever they felt like it. Sometimes, even for emails that were a reply to an email coming from their own servers. I almost lost a client because of that once. Maybe it was because of the IP range (I was in a cheap Scaleway server)? At some point I just accepted reality and paid for a third party email server (Runbox) but the situation with the monopoly of these giants marking as spam anything they don't manage made just really sad.

calibas 5y ago
HN often talks about running your own email server like it's this wonderful example of a decentralized service that anybody can take part in. That's kind of true, but there's this whole other aspect that gets ignored. Email is not this wonderful, democratic system of equals. Email is more like a school playground where a handful of enormous bullies control everything. You either learn to work with them, cater to their demands, or you'll never be able to visit large sections of the playground. Gmail is relatively easy to appease, mostly just configuring your nameservers and email headers to Google's standards, then slowly building "reputation". Hotmail will block an entire domain (IP?) randomly every few years, then you fill out one of their infamous forms and pray they unblock you quickly. Yahoo (technically Verizon now) is even more difficult to work with, they block you out of nowhere and I've never figured out how to appeal. Seems like they do some kind of ratelimiting for smaller email servers, I don't know if it's some kind of punishment or just by default. Then there's the dozen other major email providers. Some easy to work with, others not so much.
- trulyme 5y ago
  > Gmail is relatively easy to appease, mostly just configuring your nameservers and email headers to Google's standards,... Do you mean SPF, DKIM and DMARC or something else? I will check the records again, just in case, but afaik they are perfect and Gmail still often classifies my mail as spam. It is annoying as hell (and your comparison to playground bullies is very apt).
  - calibas 5y ago
    SPF, DKIM and DMARC, but there's other factors as well. Gmail will usually tell you exactly why something was flagged spam. If you go to "Show Original" SPF, DKIM and DMARC should all show "PASS" if everything is configured correctly.
    - trulyme 5y ago
      Interesting, didn't know that as I don't use gmail myself. Thank you!
    - sarkron 5y ago
      Hmm, not always. I've just setup my own mail server, I PASS SPF, DMARC and DKIM according to Gmail headers and yet my email is still classified as spam, as determined by "Gmail magic". I believe this is because the domain is relatively new and Gmail treats you as guilty until you prove your innocence (ie. Enough people mark my emails as not spam)
      - smartbit 5y ago
        Try adding an IPv6 address. Got the tip here on HN.
xhkkffbf 5y ago
I have one domain that uses Google's G suite. But sometimes when I send mail from this domain to a gmail address it gets marked as spam. It doesn't leave Google's network or cloud of servers, but they flag it. It's not a very good system.
traceroute66 5y ago
> I did run my own server with properly setup DKIM and SPF and all Ah. But the million dollar question is WHERE did you run that server? If you ran it off your home connection then there's your problem. Pretty much everyone on the receiving end (ISPs, corporates etc.) will either block or assign a low reputation to home ISP IP ranges. So basically you can do all the DKIM and SPF you like on your home MX server, but you're going to have the high hurdle of your untrustworthy IP range to fix first ! EDIT: Just saw you said "cheap Scaleway" ... well that's a similar sort of problem. Perceived "spammer friendly" hosts tend to be assigned a low rep in spam scanning. You won't be auto-blocked like residential IPs are, just a low rep set. (for any lawyers reading, I am NOT making any comment on Scaleway here, I am speaking in general terms !)
rsync 5y ago
"Gmail and Hotmail would still mark my emails as spam whenever they felt like it. Sometimes, even for emails that were a reply to an email coming from their own servers. I almost lost a client because of that once. Maybe it was because of the IP range (I was in a cheap Scaleway server)?" Like you, I have properly set up DKIM and SPF and blah blah. I also have a 12 year "clean" IP from he.net. Sometimes gmail will mark something I send as spam that is, like yours, a reply to their user and is a recipient that I have a years long history of corresponding with. That's frustrating but what really makes me angry is that there is no indication given that this occurs. Why can't google send a proper bounce or warning message ... or even an error code that I could at least see in my logs ? In the arms race between spammers and (providers) are error indications exploited in some way ? Or is google just being lazy ?
- arximboldi 5y ago
  That's so frustrating. The biggest AI company in the world and their anti-spam system is so stupid? Really lowers your expectations on state of the art tech.
  - gambler 5y ago
    They're not stupid. It's part of a sophisticated long-term strategy. They deliberately make things complicated to maintain so that you give up and use their services. This strategy is working. Many small and mid-sized businesses today gave up on email maintenance altogether and outsourced it to either Google or Microsoft. Many individuals end up using Gmail, because it seems more "reliable" now that so many other people are on Gmail.
    - rsync 5y ago
      From my cold, dead hands ...
    - lytefm 5y ago
      I have a similar impression from dealing with deliverability issues. Relevant providers usually just require a few days of sending legit mail and occasionally asking to be unblocked, but there seems to be no chance getting into the inbox on GMail and Outlook with a "too low" sending volume. If it wasn't for regulations, I would have already given up and switched to GMail.

calibas 5y ago

HN often talks about running your own email server like it's this wonderful example of a decentralized service that anybody can take part in. That's kind of true, but there's this whole other aspect that gets ignored. Email is not this wonderful, democratic system of equals. Email is more like a school playground where a handful of enormous bullies control everything. You either learn to work with them, cater to their demands, or you'll never be able to visit large sections of the playground. Gmail is relatively easy to appease, mostly just configuring your nameservers and email headers to Google's standards, then slowly building "reputation". Hotmail will block an entire domain (IP?) randomly every few years, then you fill out one of their infamous forms and pray they unblock you quickly. Yahoo (technically Verizon now) is even more difficult to work with, they block you out of nowhere and I've never figured out how to appeal. Seems like they do some kind of ratelimiting for smaller email servers, I don't know if it's some kind of punishment or just by default. Then there's the dozen other major email providers. Some easy to work with, others not so much.

trulyme 5y ago
> Gmail is relatively easy to appease, mostly just configuring your nameservers and email headers to Google's standards,... Do you mean SPF, DKIM and DMARC or something else? I will check the records again, just in case, but afaik they are perfect and Gmail still often classifies my mail as spam. It is annoying as hell (and your comparison to playground bullies is very apt).
- calibas 5y ago
  SPF, DKIM and DMARC, but there's other factors as well. Gmail will usually tell you exactly why something was flagged spam. If you go to "Show Original" SPF, DKIM and DMARC should all show "PASS" if everything is configured correctly.
  - trulyme 5y ago
    Interesting, didn't know that as I don't use gmail myself. Thank you!
  - sarkron 5y ago
    Hmm, not always. I've just setup my own mail server, I PASS SPF, DMARC and DKIM according to Gmail headers and yet my email is still classified as spam, as determined by "Gmail magic". I believe this is because the domain is relatively new and Gmail treats you as guilty until you prove your innocence (ie. Enough people mark my emails as not spam)
    - smartbit 5y ago
      Try adding an IPv6 address. Got the tip here on HN.

xhkkffbf 5y ago

I have one domain that uses Google's G suite. But sometimes when I send mail from this domain to a gmail address it gets marked as spam. It doesn't leave Google's network or cloud of servers, but they flag it. It's not a very good system.

traceroute66 5y ago

> I did run my own server with properly setup DKIM and SPF and all Ah. But the million dollar question is WHERE did you run that server? If you ran it off your home connection then there's your problem. Pretty much everyone on the receiving end (ISPs, corporates etc.) will either block or assign a low reputation to home ISP IP ranges. So basically you can do all the DKIM and SPF you like on your home MX server, but you're going to have the high hurdle of your untrustworthy IP range to fix first ! EDIT: Just saw you said "cheap Scaleway" ... well that's a similar sort of problem. Perceived "spammer friendly" hosts tend to be assigned a low rep in spam scanning. You won't be auto-blocked like residential IPs are, just a low rep set. (for any lawyers reading, I am NOT making any comment on Scaleway here, I am speaking in general terms !)

rsync 5y ago

"Gmail and Hotmail would still mark my emails as spam whenever they felt like it. Sometimes, even for emails that were a reply to an email coming from their own servers. I almost lost a client because of that once. Maybe it was because of the IP range (I was in a cheap Scaleway server)?" Like you, I have properly set up DKIM and SPF and blah blah. I also have a 12 year "clean" IP from he.net. Sometimes gmail will mark something I send as spam that is, like yours, a reply to their user and is a recipient that I have a years long history of corresponding with. That's frustrating but what really makes me angry is that there is no indication given that this occurs. Why can't google send a proper bounce or warning message ... or even an error code that I could at least see in my logs ? In the arms race between spammers and (providers) are error indications exploited in some way ? Or is google just being lazy ?

arximboldi 5y ago
That's so frustrating. The biggest AI company in the world and their anti-spam system is so stupid? Really lowers your expectations on state of the art tech.
- gambler 5y ago
  They're not stupid. It's part of a sophisticated long-term strategy. They deliberately make things complicated to maintain so that you give up and use their services. This strategy is working. Many small and mid-sized businesses today gave up on email maintenance altogether and outsourced it to either Google or Microsoft. Many individuals end up using Gmail, because it seems more "reliable" now that so many other people are on Gmail.
  - rsync 5y ago
    From my cold, dead hands ...
  - lytefm 5y ago
    I have a similar impression from dealing with deliverability issues. Relevant providers usually just require a few days of sending legit mail and occasionally asking to be unblocked, but there seems to be no chance getting into the inbox on GMail and Outlook with a "too low" sending volume. If it wasn't for regulations, I would have already given up and switched to GMail.