This is a painful reminder that technical deliverability and domain reputation will silently kill a product faster than poor user experience ever could. Switching to a custom domain triggers strict spam filters on major email providers, proving that setting up proper DNS authentication (SPF, DKIM, and DMARC) and warming up a brand-new domain from day one are non-negotiable fundamentals for any launch.
Agreed in general, but my case argues slightly against the standard advice, so it's worth being precise. SPF, DKIM and DMARC were all correct and aligned before the first message went out, and PTR matched in both v4 and v6. Gmail and Zoho took it immediately. Outlook binned it anyway.
Authentication is what gets you evaluated, not what gets you delivered. Microsoft is the one big provider where a domain nobody has seen before starts below zero and has to earn its way out with volume that doesn't generate complaints. That's the annoying part: every check you can run is green and the mail is still in the junk folder.
12 paying customers this early makes the reliability problems much more consequential.
Curious whether the bigger risk now is Outlook reputation taking time to improve, or proving the IMAP migration can handle large real-world archives without creating trust-killing duplicates or missed mail.
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I got a $420 Google Workspace bill for five people, and two of them barely used it. A mail server doesn't care about headcount, it cares about storage. So I built one that charges for storage. $9 a year.
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