A deep dive into email deliverability in 2024

Core deliverability mechanisms

• SPF, DKIM, and DMARC are viewed as table stakes: without them, inbox placement at major providers is “near impossible.”
• Several commenters stress these records are necessary but not sufficient; real-world delivery also depends heavily on domain/IP reputation, volume history, and complaint rates.
• Some note DKIM isn’t strictly required in all cases (e.g., per new Google guidelines if SPF is correct), but others argue DKIM is critical for forwarding scenarios.

Experiences with major providers

• Microsoft/Office365 is repeatedly described as the hardest to deliver to: random spam-folder placement, opaque blacklisting, and DKIM failures despite correct setup.
• Gmail and Yahoo generally behave better for some self-hosters, but others report sporadic rejections tied to “bad domain reputation” despite spotless histories.
• mac.com/iCloud/Proofpoint are also cited as problematic, with soft bounces, junk-folder placement, and minimal feedback or DMARC reporting.

Self‑hosting vs third‑party services

• Many report that long-running, correctly configured personal servers still get blocked or blacklisted (often due to neighboring IPs or /24 blocks).
• Common workaround: relay through services like SES, SendGrid, Mailgun, or Google Workspace; but shared-IP pools can be tainted by other customers.
• Some see this ecosystem as effectively a cartel/monopoly that pushes senders toward big platforms.

Forwarding, mailing lists, and DMARC

• Classic forwarding breaks SPF; DKIM generally survives, so DMARC should pass if DKIM aligns.
• In practice, forwarding and mailing lists often fail DMARC due to:
  • Subject/footer modifications that break DKIM.
  • Lack of SRS or ARC at forwarders.
  • Microsoft and Apple occasionally mangling messages.
• There’s disagreement over whether new 2024 policies fundamentally “break” forwarding or merely enforce long-standing rules more strictly.

Bulk mail, unsubscribe, and user behavior

• Gmail’s requirements around List-Unsubscribe (not strictly “one-click on the page”) are discussed; confusion exists about what is mandatory.
• Users complain about painful unsubscribe flows, click-tracking domains blocked by ad blockers, and multi-day “unsubscribe delays,” leading many to prefer “Report spam.”
• Some explicitly never unsubscribe from unsolicited mail, considering links unsafe and instead relying on spam-reporting and better providers.

Abuse, attacks, and reputation games

• Hypothetical “targeted failed deliverability” attacks via mass spam-reporting are discussed; some think third-party monitoring and separate domains/subdomains mitigate this, others see real risk for small orgs.
• Bulk marketing from big brands, political campaigns, and even major free-mail accounts is often perceived as indistinguishable from spam.
• There’s ongoing tension between those who say “it’s not that hard” and others who view opaque, centralized reputation systems as the core unsolved problem.