I've worked extensively with Microsoft support on deliverability issues, and I don't think it's a case of the right hand not talking to the left, it's a case of support wanting to close out issues as quickly as possible due to misaligned incentives. Microsoft has zero incentive to help small-time senders like the OP, since recipients are much more likely to blame the OP for delivery issues than Microsoft. Plus, Microsoft has no way of knowing for certain whether the OP is legitimate, so if they choose to help them, they might accidentally help a spammer. Therefore, Microsoft support is incentivized to simply ignore complaints like the OP or give them the run-around, which has been my experience.

The only part of the article that surprised me is the fact they actually got the issue escalated. I've never succeeded in doing that; talking to Microsoft support is like talking to a brick wall.

> talking to Microsoft support is like talking to a brick wall

I once had DKIM keys get out of sync with DNS in Office 365. It’s supposed to be handled automatically and that should never happen. Support was as useful as a baby trying to do calculus. It took me 3 days to get the keys rotated and after I understood how it works I realized they should have been able to help me mitigate it right away (dkim keys can be rotated while disabled).

> The only part of the article that surprised me is the fact they actually got the issue escalated. I've never succeeded in doing that; talking to Microsoft support is like talking to a brick wall.

I’ve found that the best trick with Microsoft is: money talks. If you pay them for support suddenly you should have a much easier time getting things done.

Obviously paying MS to fix a problem they caused is abhorrent but sometimes you gotta hold your nose and do it.

> I’ve found that the best trick with Microsoft is: money talks.

It depends on the quantity. MS365 Business Basic/Premium customers are basically testers for the enterprise offerings. Look at release cadences for the different tiers and it becomes obvious.

Does Smart Screen filter email originating from within the organisation that sends it?

My organisation used to self host everything -- wonderful times; everything worked, but with a HTML 1.0 crappy web interface. About four years ago they shifted to Exchange (urgh -- suddenly IMAP errors and some of my message-read state information became lost. I also noted the massive decrease in my Mac's battery life as Mail seemed to have a lot more work to do -- but I digress) and about two years ago self-hosted exchange became O365.

They recently started pushing harder into moving everything into Microsoft's cloud, and my quality of life has massively decreased -- the first time I was driven insane by it was when my colleague's human-written emails to me ended up in my spam folder; and vice versa when I emailed six undergraduate students to set a date and time for a tutorial. I turned up, they didn't, as I'd been shadowbanned from sending a five-line message to recipients within the same organisation -- messaging them all together got it dropped, sending it individually without the CC was fine. I complained and got given the run-around for a few weeks with no answer. The response of my local "IT people" was "not our fault mate".

The other thing I particularly hate about Microsoft 365 is that all the user-facing error messages are "Sorry, something went wrong". I'm not an idiot, please don't treat me like one.

> All opinions are my own and not that of Microsoft.

Having to write this is so ridiculous. Better just use a throwaway and be yourself. Or is this PR?

No, PR never admits to the management problems that are endemic to the company.

PR will mention a minor technical problem that has been solved, nothing to worry about.

I had exactly same experience as author, however I didn't have enough perseverance to go that far. Changed IP and it worked.

Not sure how things are organised in microsoft, but it's one of worst support ever happened to me

The problem, of course, is that Tier 1 support are outsourced and a huge part of their evaluations are how many tickets they close. Escalating hurts their numbers, so it's hard to get cases escalated, especially if you're not a paying customer.