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Comment on Microsoft Silently Dropping Emails – a Sad but True Story (2020)

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I'm currently having the same experience.

Unlike virtually all other email providers, Microsoft does not cooperate if you follow standard email practices. You can follow all their instructions, sign up for their monitoring tools, submit issue reports, try to build "reputation" and if you are self-hosting they will still have a high likelihood of silently dropping your emails after their server tells you it got them, or putting them in the recipients spam even after being marked as an approved sender.

Unforgivable. Literally destroying the decentralized nature of one of the last few "decentralized" systems that exists. For shame

“Email is so unreliable. Have you tried Teams?”

Just ignore that it’s Microsoft breaking a legacy standard to advantage their other products that compete against email. I think they should start fining companies in stock. Dilute the shareholder value by 5% and see how quickly things change.

Teams

Moving back to a full MS stack after 15ish years away from it is so disappointing. I’d assumed things had got better.

Their previously good products are now some sort of split personality monster that sort of work together but mostly just exist near each other and have a common logo. Teams is a mushy world between the distant parts.

Go on, try change a footer on a “Word” document or move an image. Try and copy a document and change its contents and re-upload. It might work, and it might work most the time. But when it goes wrong it’s devastating.

It's almost easier centering divs in CSS. And that's saying a lot... Lol!

That's basically my experience administering Microsoft 365 at my last job.

I like this, let's start a club

Yep. My Dad's company uses a small hosting provider so he cannot email me @live anymore.

Have you considered switching to a better email provider than @live then?

Try to email your dad first. If you're the one initiate the conversation, then your dad will be able to reply to that same thread. After that, add him to contact list once he responded. The point is to make an attempt of your self initiate the connect to that server.

Doesn't always work. I've seen Outlook 365 or whatever it is mark a reply as spam. It's rare, but apparently not impossible.

Try adding him to your contact list.

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