As much as we try, mail from Gmail is not spam free. As such, sometimes our mail gets blocked.
Mail from third party mail clients using Gmail can be different in a variety of ways. One large one is that the IP address of the client is in the headers of the message. This is mostly for historical reasons, as messages sent via smtp.gmail.com have tended to be spammier, and giving out those IPs helps other isps block the mail better. So, it may actually be a problem with the IP space you're sending from. Or maybe your machine is infected with a botnet, so it's on a block list. In addition, the composition of the message is up to the client. Email message formatting has a lot of choices, but each client tends to make certain choices. Some anti-spam systems will look for certain features of the message that may be different, or build a signature of a variety of message composition choices, and use those in reputation systems or machine learning systems to make a spam decision. Perhaps mailpile is used by spammers, or maybe they use some email message library that spammers often use, so the message composition is similar to spammy messages. It is unfortunate that the spammers have made such choices necessary. It is unfortunate that the mail system of your recipients can't better differentiate between spam and not (well, assuming you aren't a spammer) As one can imagine, the legal system is typically ill equipped to deal with these issues in such systems which change so quickly in battle. The legal system is necessarily slow, and mostly geographically bound, making it pretty useless to stop attacks that are measured in minutes and may come from anywhere or everywhere in the world. Everything is terrible. It is wise to understand what you can control. As the saying goes, of it hurts when you do X, stop doing X. There are a lot of mail clients you can use. You could ask the mailpile folks to change their messages. You could switch from Gmail. You can point out the issue to your receivers. I imagine O365 gives their admins various controls to override the spam verdicts that they could try. Gmail provides a user level filter to whitelist mail, I'd be surprised if Outlook doesn't as well. Gmail also learns to whitelist automatically as they keep clicking not spam, dunno about Outlook. Brandon On Wed, Oct 31, 2018, 7:19 AM Steve Dodd <steved...@gmail.com wrote: > It's been suggested to me off-list that if I mention the recipient domains > I am having problems with, it might help. They are: > > kent.gov.uk > seap.org.uk > > The sender domain is gmail.com. As I said, baffled by how something with > valid Gmail DKIM & SPF could be thrown on the floor like this. > > Steve > > On Fri, 26 Oct 2018 at 14:18, Steve Dodd <steved...@gmail.com> wrote: > >> 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 >> > _______________________________________________ > mailop mailing list > mailop@mailop.org > https://chilli.nosignal.org/cgi-bin/mailman/listinfo/mailop >
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