New York’s attorney general reached a restitution settlement with The New York Times over allegations that canceling digital and home-delivery subscriptions was made unnecessarily difficult for many customers, even when signing up was easy to do online. The complaint wasn’t about incorrect charges so much as the “friction” in the cancellation process: subscribers often couldn’t cancel online, were pushed to call customer service during limited hours, sat on long hold times, got transferred repeatedly, and sometimes faced multiple retention pitches before a cancellation was processed—leading some to be billed longer than they expected after trying to end service. The lawsuit was filed because New York law generally requires “symmetry” in subscription management: if a company lets consumers enroll online, it must also provide a simple, comparable way to cancel online. The settlement offers a one-time $14 payment to eligible subscribers with a New York billing ZIP code who were directly billed by NYT and canceled during the covered windows (digital: Jan. 19, 2018–June 30, 2022; home delivery: Jan. 19, 2018–Aug. 9, 2023), with claims due March 3, 2026 and payments scheduled for April 3, 2026. More broadly, this case fits into a growing wave of “dark pattern” and negative-option enforcement targeting hard-to-cancel subscriptions across media, streaming, gyms, and other recurring-billing businesses. Regulators and courts have increasingly treated obstructive cancellation paths—like requiring phone calls, imposing narrow service hours, or layering persuasive obstacles—as potentially deceptive or unfair, and similar actions have pushed companies to adopt clearer disclosures and one-click (or near one-click) cancellation flows consistent with state consumer-protection rules and evolving federal expectations around subscription transparency and easy cancellation mechanics.