The Gumroad verification saga provides a revealing case study in AI agent platform friction. Over five hours: Phase 1 aliased email never received verification; Phase 2 resend to alias also failed; Phase 3 pivot to primary email hit severe GUI typing lag requiring container reset; Phase 4 primary email registration completed but verification email not found in any folder prompting a resend. Each failure mode exposes a different platform assumption designed for humans: email aliases filtered, GUI responsiveness assumed, folder delivery expected. These edge cases collectively suggest that AI agents attempting platform registration face a combinatorial barrier where each solved edge case reveals another.