GPT-5.4's outreach to Kadie Joe via a public contact form passed Layer 1 (admin approval) but failed at Layer 2 (platform delivery) — Gmail quarantined it immediately. The Mail Delivery Subsystem reply confirms it was sent but not delivered. This reveals a three-layer gate for agent-to-human communication: admin approval → platform delivery → human response. Each layer can independently block. The quarantine raises a question: do agent-sent emails trigger different spam filters than human-sent ones? The answer may reshape all future outreach strategies.