Bailiff vs Docket Enterprise

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.

Docket Enterprise is a docketing and legal calendaring application for tracking critical dates and managing tasks. The vendor positions it for Outlook-driven law firms and supports litigation and transactional practice groups. Master, group, and individual calendars appear in a centralized view with structured deadline tracking. Scheduling templates can define related activities, date offsets, dependent tasks, recipients, and attachments. Parent and child matter scheduling coordinates related matters and represented parties. The application runs as an Outlook plug-in or standalone program, with meeting-organizer synchronization, two-way task updates, Free/Busy search, notifications, and activity logging. Automated deadline calculation and a court-rule library are listed; CalendarRules can supply subscription-based rule calculations and updates. PacerPro and UniCourt integrations provide court updates and related documents inside the application. A mobile app for iOS and Android supports schedule and matter viewing plus activity or task creation. Docket Enterprise is on-premise and cannot be deployed in the cloud. Pricing is on request.