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Privilege logging is one of the most time-consuming, expensive, and contentious components of discovery. Federal Rule of Civil Procedure 26(b)(5)(A), which governs the withholding of privileged material, provides little concrete guidance to alleviate these burdens. But the broad language of the rule also offers litigants significant flexibility to incorporate new technology, most notably automation and artificial intelligence, into their privilege logging practices. These tools meaningfully increase efficiency and cost savings for many litigants and should be more widely adopted as the technology progresses.