The explosive growth of the Internet was supported by the Communications Decency Act (CDA) and the Digital Millennium Copyright Act (DMCA). Together, these pieces of legislation have been credited with shielding Internet intermediaries from onerous liabilities, and, in doing so, enabled the Internet to flourish. However, the use of machine learning systems by Internet intermediaries in their businesses threatens to upend this delicate legal balance. Will this affect the intermediaries’ CDA and DMCA immunities, or expose them to greater liability for their actions? Drawing on both substantive and empirical research, this paper concludes that automation, as used by intermediaries, largely reinforces their immunities. In consequence, intermediaries are left with little incentive to exercise their discretion to filter out illicit, harmful and invalid content. These developments brought about by AI are worrisome and require a careful recalibration of the immunity rules in both the CDA and DMCA to ensure the continued relevance of these rules.