Symptoms#
- Messages landing in spam despite previously good placement
- Bounces mentioning policy, authentication, or reputation
- Provider dashboards showing a drop in reputation or authentication pass rate
Diagnosis steps#
- Confirm the configuration is live: query DNS from an external resolver and check the sending platform's settings page.
- Send to a seed mailbox and read the full headers, especially Authentication-Results.
- Compare the domains in From, Return-Path, and DKIM d= for alignment.
- Check provider dashboards (Google Postmaster Tools, Microsoft SNDS) for reputation and error rates.
- Review recent changes: new vendors, DNS edits, list imports, volume spikes.
Likely causes#
- Auto-replying to a 'please remove me' with another pitch.
- Missing opt-outs phrased informally ('not interested, thanks').
Fix and re-verify#
- Define reply categories and the action for each (book meeting, pause 60 days, remove, forward).
- Route replies through a classifier before any automated response.
- Draft responses for review; auto-send only low-risk categories like out-of-office acknowledgments.
- Log every classification for audit and model tuning.
Frequently asked questions#
Can AI reply to prospects automatically?
Technically yes. Practically, keep a human approving anything that commits your company to a meeting or claim.