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Hotmail hates non-Hotmail: is there a cure?

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rjbull:
I'm in a photography class, and send photos to the tutor's Hotmail address.  Most of the time my messages end up in her spam folder and she has to move them over manually, despite repeatedly telling Hotmail that my address isn't spam.  Now I hear from a friend who sends lots of emails to members of a club that all the messages that he gets returned as "undeliverable" also have Hotmail addresses.

Has anyone else noticed this?  Is there a cure for it?  And is Hotmail accessible by POP3, or web interface only, as it seemed to be when I tried year or two back?

Thanks...

rgdot:
If Hotmail supports filters for incoming mail that should work better than marking anything 'not spam'

Shades:
No, the mail server you use to send your email message(s) to Hotmail appears not to be configured as the email server at Hotmail expects it should be. Because of that any message that it receives from the mail server that you use will be regarded as spam. Always, that is until the mail server admin(s) at Hotmail decide that mail messages from your mail server should be thrown away immediately. Then those won't even be delivered in the SPAM box of the receiving mail account anymore.

Has to do with certified domains, DMARC, reverse DNS settings, the server you use being on a blacklist of sorts, SPF, DKIM....any configuration error on your mail server in any or all of these items I just mentioned can be enough to trigger the mail server at Hotmail to mark your messages as spam.

Mail services like Google's GMail, Hotmail and pretty much all mail services you need to pay for have all the things I mentioned configured correctly and won't give you problems sending mail to Hotmail. But if you use an obscure service, get a better mail service. Because these items are known for a while now and any professional mail service have these items applied on their mail server(s).

What mail server and/or service do you use to send your mail with? Or do you run your own private mail server? In that case, you must start to read up and apply these items as soon as possible, because more and more mail servers apply these to combat spam. While some items can be added rather easily to your own mail server, others require contact and configuration at the end of the service where you get your IP addresses from.

rgdot:
I have had yahoo's own messages - I mean their own announcements not other yahoo user emails! - go to my yahoo spam. A (very) few times same has happened with gmail and hotmail. Email is never 100%, will never be, even with the best up to date and secure settings. Another a bit common example of this is when services miss obvious spam and it lands in your inbox or kind of opposite when twitter notifications land in spam for example. I would NOT recommend trying to fix server settings unless the recipeints are comfortable or are not inconvenienced dealing with the next time it fails. Slack groups and such are far better communication method.

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