4 ms·

Thats not entirely true. Microsoft is crazy on what it flags, and their AI straight just does "things". Their support has admitted as much when i had tickets op

Thats not entirely true. Microsoft is crazy on what it flags, and their AI straight just does "things". Their support has admitted as much when i had tickets open for months trying to white list basic GNU/Hurd list serves (that I didnt run). Im sure just running Mail in a Box on linode would 100% flag it. I KNOW google would because half the time i socks through one of my linodes (that i have used and owned the IP for years on) i get thrown through all sorts of captchas on services. INCLUDING signing into my own gsuite from it (despite an established history of just doing it). Unfortunately the big players own mail, they do what they want. In fact having a domain registered with one will do better for your mail reputation than most would care to admit. Just look at how MS uses SMTPS on port 25, sure they COULD use 587 or 465, but they dont: https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/use-connectors-to-configure-mail-flow/set-up-connectors-to-route-mail https://docs.microsoft.com/en-us/exchange/mail-flow-best-pra...

mindslight 5y ago
I run postfix on Debian on a longstanding Linode, haven't gotten around to setting up DKIM, and emails to businesses served by outlook.com go through just fine. I'm not rejecting the concern or the ambiguous worry about arbitrary judgement, but the surveillance web's captchas are much more draconian than spam filters.
- croutonwagon 5y ago
  You are probably right to an extent and I was probably over dramatizing it with the whole 100% part. But having managed email across all three providers. Microsoft does just ignore rfc’s and basic standards pretty regularly and relies heavily on “AI”. Google less so. And when it works it works great. But once you get deliverability issues it’s a pain to resolve with them. Especially if you have to engage support.
  - judge2020 5y ago
    > Especially if you have to engage support. If i'm running an email inbox, responding to support regarding email deliverability is my lowest priority primarily because, if I respond once, it becomes an attack vector for dedicated spammers to try to extract information about the spam detection systems.
    - croutonwagon 5y ago
      Thats more or less an argument FOR using one of the large providers. Frankly you are more likely to make exceptions and monitor internally for deliverability from a google, or outlook.com or comcast.net than for some random xyz.email domain. And blocking swaths of those has a bigger impact. Frankly though, imho, you should respond to users that report deliverability issues on your domain and tweak your spam filters accordingly. Just ignoring a users saying "i am not getting expected emails from this listserve" is a great way to encourage your users to employ shadow IT and just use personal accounts. Obscurity isnt security, even with spam mitigations. Things like SPF, DKIM, DMARC along with some user impersonation filtering (including spoofing from fields) is basic spam 101 and will catch 99% of your actual security related phishing.And the largest ones (dmarc) can be probed publicly anyhow since almost all of it relies on DNS txt records.

mindslight 5y ago

I run postfix on Debian on a longstanding Linode, haven't gotten around to setting up DKIM, and emails to businesses served by outlook.com go through just fine. I'm not rejecting the concern or the ambiguous worry about arbitrary judgement, but the surveillance web's captchas are much more draconian than spam filters.

croutonwagon 5y ago
You are probably right to an extent and I was probably over dramatizing it with the whole 100% part. But having managed email across all three providers. Microsoft does just ignore rfc’s and basic standards pretty regularly and relies heavily on “AI”. Google less so. And when it works it works great. But once you get deliverability issues it’s a pain to resolve with them. Especially if you have to engage support.
- judge2020 5y ago
  > Especially if you have to engage support. If i'm running an email inbox, responding to support regarding email deliverability is my lowest priority primarily because, if I respond once, it becomes an attack vector for dedicated spammers to try to extract information about the spam detection systems.
  - croutonwagon 5y ago
    Thats more or less an argument FOR using one of the large providers. Frankly you are more likely to make exceptions and monitor internally for deliverability from a google, or outlook.com or comcast.net than for some random xyz.email domain. And blocking swaths of those has a bigger impact. Frankly though, imho, you should respond to users that report deliverability issues on your domain and tweak your spam filters accordingly. Just ignoring a users saying "i am not getting expected emails from this listserve" is a great way to encourage your users to employ shadow IT and just use personal accounts. Obscurity isnt security, even with spam mitigations. Things like SPF, DKIM, DMARC along with some user impersonation filtering (including spoofing from fields) is basic spam 101 and will catch 99% of your actual security related phishing.And the largest ones (dmarc) can be probed publicly anyhow since almost all of it relies on DNS txt records.