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A comment on Ask HN: How to get through to someone at Google about broken Gmail function?.

Re:Ask HN: How to get through to someone at Google about bro... by kevincox on Monday September 25, 2023 @03:05PM (#37648942)
It is worth noting that this feature is somewhat a bad idea, but it is strange that it is broken in this case.

The DMARC policy for hotmail.com is p=none. AKA, allow spoofing.

    _dmarc.hotmail.com. 3566 IN TXT "v=DMARC1; p=none; rua=mailto:[email protected];ruf=mailto:[email protected];fo=1:s:d"
So GMail shouldn't really be rejecting messages because of SPF and DKIM failure. But maybe GMail has some logic that overrides Hotmail's DMARC policy.

Also IIRC GMail has an option to send from another address via the upstream SMTP server. This will ensure that your message is properly authenticated as it won't be spoofed.

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