Hope nobody minds a 'civilian' posting here.. I switched to using Mailpile (https://www.mailpile.is/) on 1st Oct (but not enabling any encryption features, etc.) About five days later I started to have real problems with deliverability to certain recipients on O365.
I'm using my Gmail account, so messages are still going out through their servers; SPF and DKIM should therefore be unchanged. The recipients in question are people I have been corresponding with for some time, so I am in their address books and there is a history of them responding to my messages. Sadly they're non technical and so can't provide me with any information. All the tests I have run with technically minded contacts who happen to use O365 have been fine, and when I've managed to get a look at the headers there is nothing untoward flagged that I can see. Absolutely baffled and having real problems running my life (O365 seems to be preferred by UK government departments and services.) I have tried sending from a Gandi-hosted domain as well, and having similar issues, even after enabling DKIM. Hints and tips gratefully received... Steve
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