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Comment by andix | Hacker News Reader

I really don’t care anymore if my email reaches Outlook or Hotmail addresses. It’s impossible to make sure. And to some extent it’s also the users problem.

With Office 365 I have far less issues. So Microsoft can do it, if they want to.

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Even Microsoft understands what it means for their business if a paying customer with access to legal representation such as a lawyer or a medical professional randomly started losing correspondence.

If it was proven in court that they were silently discarding correspondence of paying customers because they were over confident in their spam filtering, everyone would jump ship in a heartbeat.

Mail is a very resilient protocol, this isn't UDP, this is the result of a deliberate decision being taken.

Exactly, this is not "randomly losing correspondence". This is simply spam filtering that is done after accepting the e-mail for delivery. Whether that should be an acceptable behavior or not is another discussion.

I'd be interested in how anyone could defend that silently discarding email after "after accepting the e-mail for delivery" based on a defective filter is acceptable behaviour.

I believe that the argument goes that processing e-mail in spam filters can take some time, so they accept it and queue it for analysis.

Sure, and if it fails move it to the spam folder. In the article Microsoft are discarding emails because the sender hasn't got much of a reputation yet. That's a very weak reason.

If storing vaguely suspected spam is intolerably expensive then maybe just keep a list of discarded messages (sender, title and date). At least users can see what's happening.

They could still at the very least send a notification email back when the deferred analysis rejects the message. Email is multi-hop anyway in the general case.

After accepting an email for delivery, the only choices the mail server should have are "inbox" or "spam folder", not "deleted forever in a black hole".

A lot of mail servers are configured like that. Messages with very high SPAM rating are rejected, but still delivered into the SPAM folder.

The server rejects the message, to get rid of spammers. After a few rejected messages, they usually stop delivering SPAM for quite some time (it's unnecessary work to do, and a higher risk to land on blacklists).

Are you sure that the infrastructure behind Outlook and Office 365's Outlook is sufficiently different? I was under the impression that it's similar if not the same. Compare Outlook:

  $ dig mx outlook.com
  ;; ANSWER SECTION:
  outlook.com.            300     IN      MX      5 outlook-com.olc.protection.outlook.com.

with my university that is a customer of Outlook on Office 365:

  $ dig mx uniri.hr
  ;; ANSWER SECTION:
  uniri.hr.               86251   IN      MX      0 uniri-hr.mail.protection.outlook.com.

You're not wrong, but Microsoft's Exchange 365 does have a lot of knobs to control (https://docs.microsoft.com/en-us/microsoft-365/security/offi...) and the defaults are more relaxed, probably as concession to those migrating from on-premise solutions. I'm guessing that they turn the knobs into the most aggressive position for their personal services.

Even if the infrastructure is very similar, it can be set up with completely different configurations.

The free version has probably a lot of features turned off.

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