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Comment by s1mplicissimus | Hacker News Reader

I'd assume that you also never tried running your own email server and have the email actually delivered to a gmail address, then.

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I've self-hosted email systems for businesses for nearly 20 years. I've actually had far easier times delivering to Gmail/Workspace clients than Outlook. Outlook constantly breaks strict DKIM with some of their protection scanning nonsense for emails that seem to get good deliverability almost everywhere else.

Exactly. Outlook is the main source of deliverability headaches.

Isn't that a good thing? I'm quite happy with Outlook filtering out trash.

No. It will do things when shuffling the email through its various scanner platforms that will make their systems think the original sender is outlook's systems. So then when their later downstream service looks at the email it's like "cool an email from Outlook, let's see if Outlook is allowed to send for this domain...hmm...seems like outlook isn't allowed to send and I'm supposed to reject emails coming from unapproved senders so rejected!"

The way it sometimes bounces emails around in their own systems lead to them sometimes mixing up who actually originally sent the message. This causes all kinds of problems and seems entirely unique to their crappy setup.

In our case, we're a small business, and we don't do email marketing. So I'd say that anything of ours that gets dropped by Outlook isn't trash. The only non-hand-typed email we send are transactional - actually transactional as in "here's your invoice" or "here's you're tracking number".

You know, you could achieve 100% spam filtering by just deleting every email. You wouldn't see any spam at all!

That did work for decades up until recently. It took me a bit to realize that google email recipients had stopped receiving my emails.

They basically force yourself to register to their service go allow your emails to be possibly analyzed. It takes dozens or hundreds of emails to warm up a single self hosted email account

We needed a stamp.

Regulated "Emails cost 1 penny" would have worked fine. All you need to do to meaningfully fight spam is have a cost that isn't completely negligible; Spammers started out at a rate where they spend less than a day's wages to message literally every human being on the planet; At those costs even finding a single person you can convince of your Nigerian prince account nets you a profit.

We controlled the pipes and the formats in the 90's and 00's almost unilaterally. We should have made a stamp.

YMMV but I never had issues with Gmail accepting mail from my personal server. And I didn't even do anything Gmail-specific, just standard SPF+DKIM and making sure my server is not an open relay etc.

Microsoft on the other hand...

I self-host an email server and can definitely send email to Gmail addresses.

Been doing it for over 20 years without issue, for myself and many other customers.

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