I think the only way is to carefully test it, “In Combat”. Just remember, if you’re sending to the same recipient all the time, the machine will notice …
* When you start sending * If the recipient never replies * … other things. So you will need many test recipients, and careful evaluation of the results. For all receivers of concern. Aloha, Michael. -- Michael J Wise Microsoft Corporation| Spam Analysis "Your Spam Specimen Has Been Processed." Got the Junk Mail Reporting Tool<http://www.microsoft.com/en-us/download/details.aspx?id=18275> ? From: mailop <mailop-boun...@mailop.org> On Behalf Of Steve Dodd Sent: Monday, November 12, 2018 8:33 AM To: mailop@mailop.org Subject: Re: [mailop] O365 discarding mail after User-Agent change For anyone interested in this.. I had a bit of an exchange with Michael off-list, we thought he had mitigated the issue, it seems not. Reading between the lines of Michael's off-list replies, I went looking at a certain part of the Mailpile code (I intentionally won't be too precise here.) Anyway, I've just discovered an otherwise harmless bug that will make "new messages" (i.e. thread/conversation starters) look slightly different to replies, forwards, etc. This might explain why almost all the test messages I sent succeeded, but "real" mail has continued to fail. Anyway, I'm wondering generally if and how mail software authors - particularly of 'niche' software - can test and discuss interoperability with the big inbox providers. Is such discussion appropriate here? If not, is there another forum? Steve On Fri, 26 Oct 2018 at 14:18, Steve Dodd <steved...@gmail.com<mailto:steved...@gmail.com>> wrote: Hope nobody minds a 'civilian' posting here.. I switched to using Mailpile (https://www.mailpile.is/<https://na01.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.mailpile.is%2F&data=02%7C01%7Cmichael.wise%40microsoft.com%7C24e5965d95484bea8d6708d648bde589%7C72f988bf86f141af91ab2d7cd011db47%7C1%7C0%7C636776377778864272&sdata=jH8UccI69rnhPG3bPtFt5%2FiJiXrkk5jeFJbVpZ7ZjqI%3D&reserved=0>) 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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