3 ms·

I tried both Sendgrid and Mailgun and couldn't reliably get mail to Gmail through either one. FWIW, I used to get a fair bit of inbound spam from Sendgrid IPs,

I tried both Sendgrid and Mailgun and couldn't reliably get mail to Gmail through either one. FWIW, I used to get a fair bit of inbound spam from Sendgrid IPs, so they floated in and out of my greylist on the regular and I wasn't too surprised when they didn't turn out to be a good option for my outbounds. I was surprised about Mailgun; I don't recall receiving any bad traffic from them ever, and the couple of times I've used them, they seem to focus a lot of energy on not being a source of trouble.

jjav 3y ago
> I tried both Sendgrid and Mailgun and couldn't reliably get mail to Gmail through either one. I mean, you can't reliably send email to gmail from gmail. It's not really the origin that's the issue, it is that gmail spam classification is quite bad. Good emails from known recipients you've corresponded actively for years will continue going to spam in gmail even as you mark them not-spam for the thousandth time. So yes, sending to anyone @gmail.com has decents odds of ending up in spam for no reason. That's just how gmail is. But no, sending it from your own email server doesn't make things worse. I run all my own email infrastructure and sending to gmail addresses works just as well from my server as it does from gmail itself.