Bailiff vs Case Calendar

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.

Case Calendar is an open-source Python command-line tool that turns federal court docket information from CourtListener into calendar feeds for hearings and filing deadlines. It creates an ICS feed per case for subscription in calendar apps that support iCalendar, and can send events one way to Google Calendar or Microsoft 365 or Outlook after a one-time OAuth setup. Its deadline tracking sends items classified as major to subscriber calendars while keeping procedural filings in an audit trail. Optional AI summaries use primary documents and dispositions, link action phrases to court documents and refresh when certain documents or event statuses change. Events retain the court’s timezone, including across daylight-saving changes. A real-time webhook can accept CourtListener updates and bypass the daily polling quota. The generated static index can be hosted behind an HTTP server. Hosted AI options include Anthropic, Google Gemini and OpenAI; local Ollama models avoid per-token API costs and keep docket text and PDFs on the host, according to the documentation. Use may incur LLM API costs and CourtListener quota limits. The project warns that docket data can lag and date extraction can miss or misread dates; it is not a replacement for attorney calendaring software.