On Wed, 31 Oct 2018 at 14:58, Ken O'Driscoll via mailop <mailop@mailop.org> wrote:
I wouldn't expect freemail addresses to get a pass anywhere. > OK, good to know - I assumed Gmail did a reasonable job of outbound spam filtering and therefore were likely to have reasonable rep. I had been considering using my own domain, but had assumed sending through an established inbox provider would be better. > Does the problem still occur when you use the Gmail web interface directly > as opposed to though an MUA? Can you categorically rule out mailpile being > the cause? > Mailpile does seem to be the trigger, but I cannot see anything terrible in the messages it is sending. Only real quirk is sending multipart/mixed with only a single part if you are not signing or attaching keys (which I'm not), but that is specifically allowed by spec. As I said, all tests run against targets using spamassassin / rspamd find nothing objectionable. Oddly, all deliberate tests run against targets running O365 (i.e., *not* recipient domains I contact on a day-to-day basis) have been OK as well, apart from one from a custom domain that got greylisted for a few hours. The only thing I can think of is that by changing MUA, I have triggered some algo that sees that as impersonation, or something. At some point I will try mutt & Thunderbird and see if that elicits the same response. Wanted to let things "settle" for a few days first though. You mention that your address is in their address books, you may also want > to try and get them to place it in their Safe Sender lists as those tend to > have more weight. > OK, thank you - I have never used Outlook/Exchange/O365 so had no idea this was a separate thing. > It is also possible that the recipients in question have created a specific > local policy which is interfering with your email. You'll really need to > speak to somebody in their IT depts. to see if this is the case. > Thanks, I am still trying but sadly people don't seem to see email deliberability as important these days, even from people who are actually their clients / service users. I am sensing lots of shoulder shrugging :( > The alternative is to send through your own domain via G Suite (or similar) > then you'd completely rule out the freemail factor. > I have run a few tests with my own domain and Mailpile, and seem to be hitting the same issues - but didn't know how much of that might be down to being a new mail source (I have my own DKIM key, but am sending through Gandi - also don't know what their IP rep is like.) That rather seems to be multiplying variables :) I do appreciate this input on this - it's driving me crazy! Not a fan of this modern world with its algorithmic overlords.. Steve
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