Information systems (IS) research has largely treated IS certifications (i.e., graphical cues that prove the endorsement of independent third parties) as universally effective at improving website visitors’ perceptions of trustworthiness. However, inconclusive findings on the effectiveness of IS certifications on websites have emerged, critically challenging their usefulness. We seek to reconcile these inconclusive findings by drawing on swift trust theory and the notion of humans as cognitive misers. Specifically, we investigate whether the effects of IS certifications are contingent on visitors’ expectations and the website’s baseline trustworthiness (i.e., the original website before adding and visitors’ processing of IS certifications). Through a multistudy investigation combining an online (N = 191) and a follow-up field experiment with up to €4 million in sales volume (N = 306), we reveal the contingent effects of IS certifications on the trustworthiness of websites: Below (but not above) a certain level of a website’s baseline trustworthiness (i.e., the trust tipping point), IS certifications significantly increase trustworthiness. We also show that IS certifications do not increase the likelihood of user registrations (i.e., trust-related behavior) when a website’s baseline trustworthiness surpasses this trustworthiness threshold. Overall, we provide an important new perspective that explains and resolves previous inconsistent findings on the (in)effectiveness of IS certifications for trustworthiness and subsequent trust-related behaviors. We equip practitioners with valuable and actionable guidance on the usefulness of IS certifications to strengthen their digital businesses.