Bailiff vs DocketCalendar

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.

DocketCalendar is a cloud-based web calendar for law firms that calculates court-rule deadlines and creates events on Outlook or Google Calendar. It can also operate as a stand-alone calendar. When dates change, it recalculates deadlines and updates or removes the related events. The rules library covers over 2,200 court rule sets nationwide; CalendarRules-powered rules are generally updated at the beginning of each month and sooner for significant changes. Custom deadline reports can be printed, exported to Excel or CSV, or copied into emails. The service stores calendaring data at case, trigger, and event levels, and settled matters can be archived. Subscriptions include unlimited support and training, with user-guide content, phone help, and screen-share sessions. Users can email the Rules Team for no-charge clarification about deadlines, counting methods, holidays, and results. The web service requires no installation or browser plugin. There is no free plan, but a free trial is available. Listed plans are $15 a month billed per court or per calendar, and $20 a month billed per user.