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Bailiff

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Spec score 8.1 #3 of 20 in Legal Calendaring Software

What it is

Bailiff is a web service for legal professionals that turns court documents into reviewable deadlines and calendar events. Users upload documents, inspect proposed deadlines, and sync approved items to Google Calendar or Outlook. Each deadline shows the triggering event, source wording, and calculation path. When a new filing arrives, Bailiff checks it against existing events so changes can be approved before calendars update. The original document remains attached to the deadline, connecting the source, calculation, review status, and calendar entry. Calendar connections use APIs, support customizable reminders and time zones, and sync one way. Bailiff says it supports court orders and scheduling documents from Florida and Texas state courts, plus all Federal courts. The Bailiff Plan costs $35 a month, billed per seat / month, and includes unlimited PDF processing, team collaboration, priority email support, Google Calendar and Outlook sync, and a 14-day free trial without a credit card. The service states that documents are processed in isolation without sharing and that connections use 256-bit SSL encryption. Customers can cancel anytime without fees, with a 30-day money-back guarantee for legal professionals.

Spec sheet

Purpose
Bailiff reads court documents, calculates deadlines, and updates calendars automatically.Read 4 Oct 2026 · getbailiff.com
Intended users
Bailiff describes itself as AI-powered deadline management for legal professionals and invites legal teams to use it.Read 4 Oct 2026 · getbailiff.com
Trial
The plan includes a 14-day free trial with no credit card required.Read 4 Oct 2026 · getbailiff.com
Integrations
Bailiff connects to Google Calendar and Outlook via API, with customizable reminders and timezone support.Read 4 Oct 2026 · getbailiff.com
Security
The site states that it uses 256-bit SSL encryption and processes documents in isolation without sharing them.Read 4 Oct 2026 · getbailiff.com
Support
The plan includes priority email support, and the site lists [email protected] as its support contact.Read 4 Oct 2026 · getbailiff.com
Audit trail
The source document remains attached to each proposed deadline, connecting it to the event, calculation, review status, and calendar entry.Read 4 Oct 2026 · getbailiff.com
Cancellation
The site says customers can cancel anytime without fees and offers a 30-day money-back guarantee for legal professionals.Read 4 Oct 2026 · getbailiff.com
Change tracking
New filings are checked against existing events so updates can be approved before calendars change.Read 4 Oct 2026 · getbailiff.com
Court coverage
The site says it supports court orders and scheduling documents from Florida and Texas state courts, plus all Federal courts.Read 4 Oct 2026 · getbailiff.com
Deadline explanations
Each deadline shows its triggering event, source language, and calculation path for review.Read 4 Oct 2026 · getbailiff.com
Workflow
Users upload court documents, review proposed deadlines and events, then sync approved items to calendars.Read 4 Oct 2026 · getbailiff.com

Plans and prices

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

Every Bailiff plan and price →

Strong points and limits

Strong points

  • Explains each deadline calculation
  • Tracks filing changes before calendar updates
  • Attached source documents provide traceability
  • Google Calendar and Outlook sync
  • 14-day trial without credit card

Limits

  • $35 per seat / month
  • No free plan
  • Calendar sync is one-way
  • Court coverage is specifically listed

Who it suits

It suits legal professionals and teams that need document-based deadline calculations, review controls, and one-way calendar updates.

Verdict

Bailiff focuses on traceable deadline extraction with a review step before calendar changes. Its stated court coverage, one-way synchronization, and per-seat subscription should be checked against a legal team’s workflow.

Where Specifiction places it

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