It's the exact same problem as the other mailop thread "Outlook.com: intermittent DKIM failures".

It's not you, it's them.

- Mark Alley

On 6/20/2025 3:36 PM, Mark Fletcher via mailop wrote:
Hi All,

We're seeing instancesĀ of emails being rejected by Microsoft with DKIM errors, and I have no idea why. It's happening to maybe 1% of the email we send to Microsoft properties (outlook.com <http://outlook.com>, hotmail.com <http://hotmail.com>, live.com <http://live.com>, etc). The error we get is:

550 5.7.515 Access denied, sending domain GROUPS.IO <http://GROUPS.IO> doesn't meet the required authentication level. The sender's domain in the 5322.From address doesn't meet the authentication requirements defined for the sender. To learn how to fix this see: https://go.microsoft.com/fwlink/p/?linkid=2319303 Spf= Pass , Dkim= Fail , DMARC= Pass

These are email group messages. We re-write the From line for all of them, so they all have the @groups.io domain. For a given list message, if it fails for one Microsoft recipient, it fails for all of them.

I dump out these emails and run two different DKIM signature check programsĀ on them, and they pass.

Does anyone have any suggestions for things I should check?

Thanks,
Mark

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