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> Gmail really pioneered the "nah, screw you" approach to this. From my POV, Yahoo pioneered this way before Gmail. 10 years ago when I was managing outgoing

> Gmail really pioneered the "nah, screw you" approach to this. From my POV, Yahoo pioneered this way before Gmail. 10 years ago when I was managing outgoing mail infra for a company that probably sent 100k emails per day (mostly purchase receipts and subscription notifications), I was intimately aware of deliverability characteristics for Gmail and Yahoo, which were our two biggest destinations by a large margin (if I recall, Gmail was about 60% and Yahoo was about 30%). Gmail, despite being the overwhelming majority of our traffic, was hardly any problem at all, whereas Yahoo would regularly give us the dreaded 451 response that indicated that your mail was going to be held for 2-24 hours and then randomly rejected or accepted. BTW, if I were to run my own mail infrastructure again, I'd definitely use someone like Sendgrid with a dedicated outgoing IP with a clean reputation. It makes a very big difference. We eventually ended up with our infrastructure split across multiple IPs by function (e.g. receipt emails were the only thing ever sent from one specific IP because we wanted to ensure deliverability).

tzs 3y ago
The trick to get reliably mail delivery to Yahoo back in the day was to be spending several thousand dollars a month buying ads through Yahoo. Then when your mails to Yahoo got repeatedly blocked by Yahoo and you got tired of having to repeatedly report the false positives and and get unblocked only to get blocked again a few weeks later you have the person in charge of your ad spending call up your ad sales rep at Yahoo. You asked the ad sales rep "Why should we keep spending $X/month on Yahoo ads to try to acquire customers, when Yahoo mail keeps blocking the receipt emails, setup instruction emails, and response emails to support questions we try to send to those customers which angers those customers and they cancel (or even try chargebacks)???". What happened then is the sales rep puts your ad manager on hold for a few moments, then comes back with someone high up in Yahoo IT management conferenced in, and explains the situation. The high IT manager puts you all on hold, and comes back in a few minutes with someone who actually deals with maintaining the spam filters conferenced in, explains the situation, and tells the maintainer to add your domain to a special whitelist of mail that is always accepted.

tzs 3y ago

The trick to get reliably mail delivery to Yahoo back in the day was to be spending several thousand dollars a month buying ads through Yahoo. Then when your mails to Yahoo got repeatedly blocked by Yahoo and you got tired of having to repeatedly report the false positives and and get unblocked only to get blocked again a few weeks later you have the person in charge of your ad spending call up your ad sales rep at Yahoo. You asked the ad sales rep "Why should we keep spending $X/month on Yahoo ads to try to acquire customers, when Yahoo mail keeps blocking the receipt emails, setup instruction emails, and response emails to support questions we try to send to those customers which angers those customers and they cancel (or even try chargebacks)???". What happened then is the sales rep puts your ad manager on hold for a few moments, then comes back with someone high up in Yahoo IT management conferenced in, and explains the situation. The high IT manager puts you all on hold, and comes back in a few minutes with someone who actually deals with maintaining the spam filters conferenced in, explains the situation, and tells the maintainer to add your domain to a special whitelist of mail that is always accepted.