Bailiff
Bailiff: Turns court documents into reviewable deadlines and calendar entries for legal teams. Ranked #11 of 20 in Legal Calendaring Software by our editors (7.7/10); pricing: 14-day trial; best for teams wanting document-to-calendar automation.
At a glance
- Editor score7.7 / 10
- Pricing14-day trial
- Best forTeams wanting document-to-calendar automation
- Free planNo
- Calendar syncOne-way
- Facts checked20 Sep 2026
Where it wins
- Extracts triggering events and calculates deadlines automatically
- Human review before syncing deadlines to Google Calendar or Outlook
- Provides source attachments, explanations, timelines, and team collaboration
Where it doesn't
- Available through the web platform only
- Calendar synchronization is one-way
- Court coverage focuses on Florida, Texas, and federal courts
Our verdict on Bailiff
Bailiff is legal deadline management software for law firms and legal professionals that need to turn court documents into tracked deadlines and calendar events. It processes uploaded court orders and scheduling documents, identifies triggering events, calculates deadlines, and prepares proposed entries for review. Coverage includes Florida and Texas state courts and all federal courts. Teams can manage case timelines, attach source documents, and collaborate around deadline tracking from the web platform.
Its main differentiator is the document-to-calendar workflow. Bailiff combines PDF processing, AI-assisted extraction, automatic deadline calculation, and human review before synchronization. Each proposed deadline can include the source document and a calculation explanation, giving teams context for how an event was derived. When new filings affect existing events, the product can provide automated updates. This makes it a focused option for teams that want more than a standalone calendar while retaining an approval step before changes reach shared calendars.
The Bailiff Plan includes unlimited PDF processing, Google Calendar and Outlook synchronization, team collaboration features, priority email support, and reasoned deadline explanations. Calendar synchronization is one-way, and the product is available through the web platform. Bailiff is a strong fit for legal teams handling supported court documents and seeking a structured review process before calendar updates. Teams needing broader jurisdiction coverage, two-way synchronization, or a non-web deployment should consider whether its focused workflow matches their operating requirements.
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Bailiff pricing
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Bailiff fact sheet
| Free plan | No |
|---|---|
| Paid from | Not verified |
| Deadline calculation | Automated |
| Court rule library | Yes |
| Statute limitations | Not verified |
| Calendar sync | One-way |
| Reminder channels | Google Calendar, Outlook |
| Supported platforms | web |
| Free trial | 14 days · no card needed |
| Money-back guarantee | 30 days |
| Deployment | Cloud |
| Platforms | Web |
| Support | |
| Built for | Small business, Mid-market (editorial estimate) |
| Integrations | 2 integrations: Google Calendar, Outlook |
| Pricing | 14-day trial (source) |
| Website | getbailiff.com |
| Facts checked | 20 Sep 2026 |
Bailiff integrations
Bailiff lists 2 integrations on its own site.
- Google Calendar
- Outlook
Alternatives to Bailiff
- CourtAlert Case ManagementA deep docket-control system for firms managing complex court workflows.9.4
- LawToolBoxA Microsoft 365-focused legal calendaring system with broad rules and platform integrations.9.1
- CalendarRulesA court-rule-focused calendaring system with broad jurisdiction coverage and one-way exports.8.9
See all Bailiff alternatives →
Also Ranked In
Bailiff is ranked in 2 of our directories.
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Reviewed by iTechGuides Editors · Editorial team · Updated Oct 2026
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