AI docketing software for solo litigators

Two things changed. First, LLMs can now read a served pleading, identify the trigger event and the jurisdiction, and hand a deterministic rules engine the inputs it needs — the intake friction that made docketing tools a paralegal's job is gone. Second, the incumbents have moved up-market: LawToolBox requires a 2-user minimum and a one-year commitment, Clio bundles court rules as a $15/user/mo add-on on top of a $39/mo plan, and MyCase gates court-rules calendaring as a premium feature. Meanwhile a free federal deadline calculator that shows its Rule 6 work was posted to Hacker News in August 2026, and Google autocomplete now suggests state-level queries (California, Texas, Florida, federal) for court deadline calculators. The demand is fragmenting into free single-jurisdiction calculators. The product that stitches rule-citing computation, AI intake and calendar sync into one $29 seat wins the solo litigator before the incumbents bother to move down-market.

Market gap

Docketing software is sold in two shapes, and neither fits a one-lawyer litigation practice. The standalone docketing tools (LawToolBox at $35–$42/user/mo with a 2-user minimum and a one-year commitment, DocketCalendar at $20/user/mo) are built around Outlook, multi-seat firms and a paralegal who owns the docket. The practice-management suites (Clio from $39/user/mo plus $15/user/mo for CalendarRules, MyCase from $50/user/mo with court rules as a premium feature) bundle deadlines into a platform the solo may not want to migrate to. Below both sits a fragmented layer of free single-jurisdiction web calculators — the SERP for 'court deadline calculator federal' is dominated by them, and autocomplete splits the query by state. The gap is a single-seat, month-to-month, $29/mo docketing tool that reads the pleading, computes the full deadline chain with the rule cited, and lives in the calendar the solo already uses.

Week 1-2: encode FRCP Rule 6 plus the civil-procedure time rules for CA, TX, FL, NY and IL as a versioned rules engine with unit tests per rule; ship the free federal calculator as a landing page with email capture. Week 3-4: LLM intake (upload or paste a pleading → trigger event, service method, jurisdiction), deadline chain generation, Google Calendar and Outlook sync, Stripe at $29/mo. Week 5-6: post the free calculator in r/Lawyertalk and r/LawFirm, cold-email 100 solo PI and family-law litigators in the five launch states, DM Capterra reviewers who complained about LawToolBox jurisdiction gaps. Month 3: add continuance recompute and the per-matter deadline memo, then expand states by inbound request volume and target 150 paying seats.