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

Re:Microsoft Silently Dropping Emails – a Sad but True Story... by anonydsfsfs on Wednesday July 28, 2021 @02:02AM (#27980648)

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.

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Re:Microsoft Silently Dropping Emails – a Sad but True Story... by donmcronald on Wednesday July 28, 2021 @02:26AM (#27980799)

> 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).

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Re:Microsoft Silently Dropping Emails – a Sad but True Story... by vxNsr on Wednesday July 28, 2021 @02:13AM (#27980721)

> 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.

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Re:Microsoft Silently Dropping Emails – a Sad but True Story... by donmcronald on Wednesday July 28, 2021 @02:29AM (#27980827)

> 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.

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