Remix.run Logo
pembrook 7 hours ago

Typically I'm a DIY type who loves tinkering and building...

HOWEVER, I have learned the hard way to never apply that spirit to email.

In Europe you see this stuff all the time with old school "IT" (what old industrial companies call tech) people balking at the prices of commercial API-based senders and email marketing ESPs.

"Money to send emails in the cloud? HAH! Back at Siemens in 90s we were running millions of emails out of our servers just fine!"

Nobody understands that deliverability has gotten immensely harder these days, and trying to DIY it if its not your core business is just plain stupid. I would never in a million years try to roll my own email, it's nightmarish legacy cruft and footguns all the way down, in everything from IP/Domain Rep to something as simple as the HTML in the email templates themselves.

Microsoft Outlook and Gmail have the last word on everything in email, and their defacto duopoly (over B2B and consumer email respectively) means you play by the rules they set in 2008 and are too lazy to change or you don't get delivered. The protocol of email exists separately from the world of the actual inbox providers, which are locked down to insane degree given the security/spam concerns with email.

jmuguy 7 hours ago | parent [-]

Google is at least less arbitrary than Microsoft. Microsoft will decide an email is spam today, and tomorrow the exact same email is perfectly fine. I think Google relies more and more on sending IP and domain reputation rather than content.

Marsymars 7 hours ago | parent | next [-]

Google regularly sends legitimate email to my spam folder.

Microsoft regularly sends legitimate emails from Microsoft to my spam folder.

oasisbob 7 hours ago | parent | prev [-]

Deliverability to Microsoft famously took a dive a bit over a year ago due to random arbitrary failures within their infrastructure causing DMARC/DKIM problems which they clearly were having problems diagnosing.

Even with a six-figure email spend and weeks of troubleshooting the best response we could get from our mail provider was that they were having problems getting traction with Microsoft on the issue.

tracker1 6 hours ago | parent [-]

Worth mentioning is that there are several email umbrellas under Microsoft... including the newer office/365, the slightly older outlook.com hosting, the old corp hosting and hotmail and sub-properties... each with different rules and services to determine spam in inconsistent ways between them.

One of my main emails is still on a "free" outlook.com hosted with a personal domain that I never shifted to paid 365. I've also got an MTA server (mailu) of my own that I've been testing with... my own email under outlook.com is literally the only one of the MS systems I can't seem to deliver to, the rest work fine. Same for google.com for that matter... kinda wild.

oasisbob 6 hours ago | parent [-]

This issue didn't seem to discriminate. I was seeing deliverability failures to Office 365 clients as well as consumer-facing brands like hotmail and msn

tracker1 5 hours ago | parent [-]

Okay... I was just adding my own experience as I was able to deliver to some without issue and not the one. It's entirely possible this has changed in the past couple years since I was actively testing.