> 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.
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.