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What practice management software got wrong about AI

The category that won the cloud era is structurally unprepared for the AI one. A diagnosis.

CWChris WatersMarch 12, 2026 · 7 min read

Overview

Practice-management software won the last decade by being a reliable system of record: matters, contacts, time, and trust accounting, all in the cloud. That design was exactly right for its era. It is also exactly why bolting modern AI onto it produces something that impresses in a demo and disappoints in a deposition.

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This essay is part of The Docket, Discover Docket's editorial hub on legal AI, ethics, and the all-in-one shift.

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