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It's very easy to get legitimate emails false-positived as spam by gmail/gsuite or office365 MX even if your sending IP address is not in a bad-reputation IP bl

It's very easy to get legitimate emails false-positived as spam by gmail/gsuite or office365 MX even if your sending IP address is not in a bad-reputation IP block, your rdns, spf, dkim and dmarc are impeccable. I know people who've been running mx/smtp servers on the internet since 1994 who have now given up on running their own, not because they're technically incapable or unwilling to continue to do so, but because they've been forced into themselves using gsuite or office365 because of the monopolistic practices of the huge email-as-a-service providers.

jrochkind1 4y ago
Are mid-tier players like FastMail screwed too? Is this a reason to be careful moving to, say, FastMail?
- daydream 4y ago
  I’ve used Fastmail for email since 2015 or so, with a custom domain, and have never had any issues with email delivery to Gmail, Office365, or any other email host. Data point of one. It’s something I occasionally worry about actually but it has never happened to me. So I probably just shouldn’t worry.
- ShamelessC 4y ago
  No.
- jasonriddle 4y ago
  I've been using Fastmail since last year, also with a custom domain. I haven't experienced any issues with deliverability so far.
- calvinmorrison 4y ago
  not really. providers have a lot of tools that monitor IP reputation, and also human contacts never hurt. Fastmail and other providers maintain their reputation by taking spam seriously and having prudent rules in place. source: i worked at fastmail and regularly got oncall alerts to go deal with some rbl issues
  - jrochkind1 4y ago
    Thanks! The OP describes carefully monitoring reputation and is their own self-hosted mailing provider (not a service-provider) so presumably isn't hosting spam... The difference may be the human contacts? Or just that self-hosted mailing providers are so rare that it's hard to keep their patterns from looking like spam to the filters? Or other?
    - calvinmorrison 4y ago
      Well the human contacts were great when something was really weird, like Apple calendars changed something and our code broke, or something kept getting flagged and you needed someone at Yahoo or such to go bang on something with a hammer. His complaint seems to be mostly about rate limiting an IP that doesn't normally send in bulk volume. It's a weird behaviour. I would recommend he not use fastmail or gmail, but an actual provider for bulk delivery. "backing off" people submitting mail, mail resending when failed, these are all really good useful parts of the email system that help you recover when things go wrong, even though it feels like a slap in the face - it's much better than the alternative of whitelist only, or blocking people permanently. It was frustrating for me sometimes.... free.fr was often on our rbl list, and if I recall it was mostly because a customer (different ones at different times) would send an email to bob@free.fr an that person was actually like bobby@free.fr, so free.fr thought you were sending crap, or spam or whatever. Usually it was just an undeliverable mail. Another thing is - IPs yes - they have "warm up" as you start sending mail out of it. In fact, providers like fastmail have a bunch of IPs, that way if one was flagged, and they figured out what was going wrong (you wouldnt just flip to the new IP, because a outbound spammer would muck up your new IP instantly), you flip over to the other IP which wasn't on any RBL. anyway, I'm probably botching the explaination, one time our anti-spam guy drew a giant whiteboard of how it all works and it gave me an instant hangover. Just to say - yes it's more complex than 'open up the port and start sending mail' but certainly not approaching 'no independent providers are allowed'
      - jrochkind1 4y ago
        Very useful info thanks! From your further description, it definitely sounds like something hard to do without significant dedicated staff -- like I could believe it is not realistic to just "run your own mail server" anymore, when mail isn't meant to be your business. For better or worse, you need to use someone where mail is their dedicated business, with the scale to devote significant resources to keeping on top of it. (an "anti-spam guy"!) Which didn't used to be the case in olden days. But, as you say, that doesn't mean it needs to be one of the big three. Is my conclusion at this point. But a "bit" (lot) more is required than one interpretation of "just taking spam seriously and having prudent rules in place" might suggest!
teddyh 4y ago
> I know people who've been running mx/smtp servers on the internet since 1994 who have now given up on running their own, not because they're technically incapable or unwilling to continue to do so, but because they've been forced into themselves using gsuite or office365 because of the monopolistic practices of the huge email-as-a-service providers. Please don’t spread the FUD that it’s impossible to run your own e-mail anymore. It’s perfectly possible. It’s just hard: https://news.ycombinator.com/item?id=32716633 https://news.ycombinator.com/item?id=32716633
- walrus01 4y ago
  This isn't FUD and I still run my own, I'm just saying that some people have given up dealing with the hassle. These are even people who have effectively free zero dollar 1U rack spaces for colo, bandwidth at the small to mid sized regional ISPs that they themselves run engineering operations at. For the record I do not endorse bowing to the pressure of the gsuite/office365 monopolists. One of the important parts that's hard to solve for a person who doesn't work at an ISP these days is that you absolutely don't want to be in a /24 netblock (and parent /22, /20, etc) that also contains $5 per month VPS/VM/hosting customers. Because the inevitable result of having shared hosting IP space where anyone with a pulse and credit card can buy a VM for one month for 5 dollars is that your IP space will end up on some blacklists/spam lists/opaque and not publicly available spam-blockage lists run by gmail, because other peoples' server IPs in the same adjacent ranges announced into global BGP tables by the same ASN have historically been a source of spam/UCE within the past 12, 24, 36 months.
  - teddyh 4y ago
    It certainly looked like FUD, but I do agree completely with everything else you wrote.
seszett 4y ago
I've been running my SMTP server since 2004 and just last week, I was finally whitelisted by Microsoft. It's the first time in 19 years that I am able to send email to @hotmail.com addresses. But other than that I have never had a big problem, it just works and I spend little time on maintaining the system.

jrochkind1 4y ago

Are mid-tier players like FastMail screwed too? Is this a reason to be careful moving to, say, FastMail?

daydream 4y ago
I’ve used Fastmail for email since 2015 or so, with a custom domain, and have never had any issues with email delivery to Gmail, Office365, or any other email host. Data point of one. It’s something I occasionally worry about actually but it has never happened to me. So I probably just shouldn’t worry.
ShamelessC 4y ago
No.
jasonriddle 4y ago
I've been using Fastmail since last year, also with a custom domain. I haven't experienced any issues with deliverability so far.
calvinmorrison 4y ago
not really. providers have a lot of tools that monitor IP reputation, and also human contacts never hurt. Fastmail and other providers maintain their reputation by taking spam seriously and having prudent rules in place. source: i worked at fastmail and regularly got oncall alerts to go deal with some rbl issues
- jrochkind1 4y ago
  Thanks! The OP describes carefully monitoring reputation and is their own self-hosted mailing provider (not a service-provider) so presumably isn't hosting spam... The difference may be the human contacts? Or just that self-hosted mailing providers are so rare that it's hard to keep their patterns from looking like spam to the filters? Or other?
  - calvinmorrison 4y ago
    Well the human contacts were great when something was really weird, like Apple calendars changed something and our code broke, or something kept getting flagged and you needed someone at Yahoo or such to go bang on something with a hammer. His complaint seems to be mostly about rate limiting an IP that doesn't normally send in bulk volume. It's a weird behaviour. I would recommend he not use fastmail or gmail, but an actual provider for bulk delivery. "backing off" people submitting mail, mail resending when failed, these are all really good useful parts of the email system that help you recover when things go wrong, even though it feels like a slap in the face - it's much better than the alternative of whitelist only, or blocking people permanently. It was frustrating for me sometimes.... free.fr was often on our rbl list, and if I recall it was mostly because a customer (different ones at different times) would send an email to bob@free.fr an that person was actually like bobby@free.fr, so free.fr thought you were sending crap, or spam or whatever. Usually it was just an undeliverable mail. Another thing is - IPs yes - they have "warm up" as you start sending mail out of it. In fact, providers like fastmail have a bunch of IPs, that way if one was flagged, and they figured out what was going wrong (you wouldnt just flip to the new IP, because a outbound spammer would muck up your new IP instantly), you flip over to the other IP which wasn't on any RBL. anyway, I'm probably botching the explaination, one time our anti-spam guy drew a giant whiteboard of how it all works and it gave me an instant hangover. Just to say - yes it's more complex than 'open up the port and start sending mail' but certainly not approaching 'no independent providers are allowed'
    - jrochkind1 4y ago
      Very useful info thanks! From your further description, it definitely sounds like something hard to do without significant dedicated staff -- like I could believe it is not realistic to just "run your own mail server" anymore, when mail isn't meant to be your business. For better or worse, you need to use someone where mail is their dedicated business, with the scale to devote significant resources to keeping on top of it. (an "anti-spam guy"!) Which didn't used to be the case in olden days. But, as you say, that doesn't mean it needs to be one of the big three. Is my conclusion at this point. But a "bit" (lot) more is required than one interpretation of "just taking spam seriously and having prudent rules in place" might suggest!

teddyh 4y ago

> I know people who've been running mx/smtp servers on the internet since 1994 who have now given up on running their own, not because they're technically incapable or unwilling to continue to do so, but because they've been forced into themselves using gsuite or office365 because of the monopolistic practices of the huge email-as-a-service providers. Please don’t spread the FUD that it’s impossible to run your own e-mail anymore. It’s perfectly possible. It’s just hard: https://news.ycombinator.com/item?id=32716633 https://news.ycombinator.com/item?id=32716633

walrus01 4y ago
This isn't FUD and I still run my own, I'm just saying that some people have given up dealing with the hassle. These are even people who have effectively free zero dollar 1U rack spaces for colo, bandwidth at the small to mid sized regional ISPs that they themselves run engineering operations at. For the record I do not endorse bowing to the pressure of the gsuite/office365 monopolists. One of the important parts that's hard to solve for a person who doesn't work at an ISP these days is that you absolutely don't want to be in a /24 netblock (and parent /22, /20, etc) that also contains $5 per month VPS/VM/hosting customers. Because the inevitable result of having shared hosting IP space where anyone with a pulse and credit card can buy a VM for one month for 5 dollars is that your IP space will end up on some blacklists/spam lists/opaque and not publicly available spam-blockage lists run by gmail, because other peoples' server IPs in the same adjacent ranges announced into global BGP tables by the same ASN have historically been a source of spam/UCE within the past 12, 24, 36 months.
- teddyh 4y ago
  It certainly looked like FUD, but I do agree completely with everything else you wrote.

seszett 4y ago

I've been running my SMTP server since 2004 and just last week, I was finally whitelisted by Microsoft. It's the first time in 19 years that I am able to send email to @hotmail.com addresses. But other than that I have never had a big problem, it just works and I spend little time on maintaining the system.