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Re:Google seems to have broken email forwarding by wpietri on Thursday March 05, 2015 @10:58AM (#9151454)
I've run my own mail server since before Google (yes, there was a time...), and I'm having similar problems. Right now I'm in the middle of a job hunt, and email from me (even to people who have already emailed me) is ending up in spam folders. It is infuriating.

It is also apparently unfixable. Regular people cannot inquire as to why mail is not getting through. And amazingly, even having friends at Google does me no good here. I'm told that the anti-spam team is so mysterious and opaque that they won't even talk to co-workers about this.

It's maddening. I get why Google grew up with absolutely no conception of customer service. (It's hard and expensive, and not necessary for their business model. Chicken farms don't have customer service windows for the chickens to lodge complaints.) But their apparent utter indifference to the problems they are creating for other people is maddening.

Re:Google seems to have broken email forwarding by keithnoizu on Thursday March 05, 2015 @11:21AM (#9151661)
Do you have the various auth headers setup on for your mx records? I have to go through that ordeal occasionally when setting up outgoing emails for sendgrid or mailchimp campaigns. There are some things you can due to reduce the likely hood of mail being auto flagged as spam although in a lot of ways it is out of your hands.
Re:Google seems to have broken email forwarding by jackweirdy on Thursday March 05, 2015 @11:24AM (#9151689)
https://www.mail-tester.com is a great tool for testing this.
Re:Google seems to have broken email forwarding by wpietri on Friday March 06, 2015 @12:33AM (#9155758)
Ooh, that is nice. Sadly, I am at 10/10, so I still have no explanation why GMail hates me.
Re:Google seems to have broken email forwarding by linkregister on Thursday March 05, 2015 @02:18PM (#9153155)
I know this may sound extortionist, but one solution is to use an email-as-a-service, like Mailgun, Sendgrid, or Mandrill. All of these services offer the first few thousand emails free. They perform spam filtering on outgoing mail so they are trusted by Email Service Providers (ESPs).

(Full disclosure: I'm an employee of Mailgun)

Re:Google seems to have broken email forwarding by linkregister on Thursday March 05, 2015 @02:20PM (#9153166)
Ideally, we'd all be able to send and receive email on our own servers, but due to the fact that the vast majority of email traffic is indeed spam, it is an unfortunate reality that the big ESPs have to be extra-cautious about it. Additionally, they need to make the decision whether email is spam or not instantaneously, so mining customers' previous emails is not an option without dramatically increasing the size of their infrastructure for this task.

It is possible to send email from your own server; you need to follow onerous industry-standard practices, like using a dedicated, known IP that has a certain amount of increasing email volume, known as "IP warming". After a few months of constant interaction with an ESP, your sender score improves. Unless you're sending massive amounts of email, the cost-benefit ratio isn't in your favor to use this method.