Bailiff vs Deadlines.com

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.

Deadlines.com provides automated, rules-based legal calendaring for smaller firms, powered by Aderant CompuLaw. It uses CompuLaw court rules and date calculations to generate legal deadlines. Users can review monthly, weekly, and daily calendars, then create, email, or print reports filtered by case, event, or date range. Outlook Sync and iCalendar export support calendar workflows. Email reminders are sent 10 business days before each deadline at 8:00 A.M.; users can adjust them in Email Preferences. A change-notification service emails users when a court rule update may affect deadlines and links to regenerate them under updated rules. The service supports web, Windows, macOS, and iPhone, with mobile calendar access and Safari compatibility on Mac and MacBook. Deadlines.com describes nationwide coverage, although a requested jurisdiction or practice area may not be available. Monthly plans are priced per case: $20 a month for 30 or more cases, 25.00 USD for 6–29 cases, 30.00 USD for 2–5 cases, or 35.00 USD for one case. Each includes unlimited users. Accounts include technical and attorney support, and user training is free.