No. 17of 21 ·Legal Calendaring Software

Bailiff

Name: Bailiff
Price: 35 USD

Web· paid plans from $35/mo

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Freedom report

One barScore 5.0

Free tierNo free tier
Runs widely1 of 6 device platforms
DocumentedPlans, terms and facts published

Bailiff is ranked #17 of 21 in legal calendaring software on Freedom251. It runs on Web. There is no free plan. A free trial is offered. Paid plans start at $35/mo.

Bailiff plans and pricing

All plans

Bailiff Plan $35/mo per seat / month 14-day free trial — no credit card · Unlimited PDF processing · Google Calendar & Outlook sync · Team collaboration features · Priority email support getbailiff.com · 4 Oct 2026

Compared on legal calendaring software

Free plan: No
Deadline calculation: automated
Court rule library: Yes
Calendar sync: one-way
Reminder channels: Google Calendar, Outlook
Supported platforms: Web

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The record

Purpose: Bailiff reads court documents, calculates deadlines, and updates calendars automatically.
Workflow: Users upload court documents, review proposed deadlines and events, then sync approved items to calendars.
Deadline explanations: Each deadline shows its triggering event, source language, and calculation path for review.
Change tracking: New filings are checked against existing events so updates can be approved before calendars change.
Audit trail: The source document remains attached to each proposed deadline, connecting it to the event, calculation, review status, and calendar entry.
Integrations: Bailiff connects to Google Calendar and Outlook via API, with customizable reminders and timezone support.
Court coverage: The site says it supports court orders and scheduling documents from Florida and Texas state courts, plus all Federal courts.
Security: The site states that it uses 256-bit SSL encryption and processes documents in isolation without sharing them.
Support: The plan includes priority email support, and the site lists [email protected] as its support contact.
Trial: The plan includes a 14-day free trial with no credit card required.
Cancellation: The site says customers can cancel anytime without fees and offers a 30-day money-back guarantee for legal professionals.
Intended users: Bailiff describes itself as AI-powered deadline management for legal professionals and invites legal teams to use it.
Price from: $35/mo

Where it ranks on Freedom251

Best Legal Calendaring Software in 2026#17 of 21

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Sources

getbailiff.com· checked 4 Oct 2026