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Deadline Pilot
Deadline | Pilotby Legal Simplicity

Created by lawyers, for lawyers

Every deadline in the order, already on your calendar.

Upload a scheduling order. Deadline Pilot reads it, calculates the dates that hang off trial and calendar call, and sends Outlook invitations to everyone who needs them.

Forward an e-service email and it downloads the filing, works out what the document actually is, and renames it to your firm's convention before you open it.

Free for your first 3 orders a month when we openEvery date editable before anything sendsBuilt for client confidentiality

How it works

01

Upload your court order

Drop any court order into Deadline Pilot — scheduling, case management, trial, or other orders.

PDF · EML · MSG
Drag, drop, or forward
02

Intelligent analysis

Deadline Pilot’s proprietary intelligence engine reads the entire document, identifies every deadline, and calculates the relative ones — “20 days after a motion is filed,” “10 days before the pre-trial conference” — from the dates the order actually sets.

AI-powered
Reads every page, end-to-end
03

Export to your calendar

One click sends calendar invitations to your entire team via Outlook, Google Calendar, Apple Calendar, or any ICS-compatible calendar application.

Outlook · Google · Apple
Standard ICS calendar invitations

Purpose-built by lawyers, for
lawyers with every aspect
designed around the way
lawyers actually work.

Intelligent Extraction

Our intelligence engine reads court orders and extracts every deadline, even from complex multi-page scheduling orders with dozens of dates, and handles batch uploads of orders as well.

Relative Deadline Calculation

Handles “30 days before trial,” “no later than 14 days after filing,” and other complex relative deadline language automatically.

Confidence Scoring

Each extracted deadline includes a confidence score assigned by our intelligence engine.

Automatic OCR

No need to OCR the order before uploading it. Our intelligence engine handles everything from start to finish.

Editable Before Export

Review and adjust any extracted deadline before sending calendar invitations. Full control before anything goes out.

Calendar Integration

Download calendar entries as an ICS file or input e-mail addresses for your team and Deadline Pilot will send the calendar entries directly.

Extraction History (Optional)

Choose to have your upload deleted immediately for privacy, or save your extraction history for later retrieval.

Enterprise-Grade Security

All documents encrypted in transit, processed securely, and NEVER shared with any third party.

Fast Processing

Most documents are processed in seconds. Eliminate calendaring delays and errors, and reclaim the time previously spent on the time consuming process of calendaring lengthy orders.

Florida e-service processing, fully automated

Our intelligence engine extracts case information, renames files using your custom naming convention, and delivers them to your team via email — including cloud download links for large attachments.

Create your own custom e-mail address (your name)
@eservice.deadlinepilot.com to forward e-service
emails to for processing, and/or to add as a secondary
address to your E-Filing Portal account for quick,
seamless, and automatic processing of new filings.
Intelligently enhanced, with renamed filing attached
Case No.:2025-CA-001234
Case Style:Johnson Medical Group v. Smith Realty
Court:11th Judicial Circuit, Miami-Dade County
Document:Motion for Summary Judgment
Filed:March 5, 2026 at 10:37 AM
E-Filing No.:143519327

Original: no attachment, only an expiring link

Deadline Pilot: Johnson Medical Group - MSJ - 3-5-26.pdf

Built for security and
client confidentiality

Your clients' data deserves the highest level of protection. Deadline Pilot is built from the ground up with enterprise-grade security at every layer.

AES-256 Encryption

All documents are encrypted at rest using AES-256, the same standard used by financial institutions and government agencies.

Hosted on SOC 2 Type II Infrastructure

Deadline Pilot runs on cloud providers that maintain SOC 2 Type II certification. The application itself is not separately SOC 2 certified; we apply equivalent operational controls and are pursuing certification.

TLS 1.2+ in Transit

Every connection to Deadline Pilot is encrypted with TLS 1.2 or higher, ensuring your documents are protected during upload and download.

No Third-Party Data Sharing

Your documents are never shared with, sold to, or accessed by any third party. Period.

User-Controlled Retention

You decide how long your data is stored. Opt in to have it deleted within 24 hours of processing, or retain extractions for your plan’s window.

Enterprise Authentication

Support for enterprise SSO, multi-factor authentication, and role-based access controls to keep your team secure.

Transparent pricing for every firm size

Free

No credit card required
$0/month

For occasional users

3 scheduling orders with calendar invitations per month
5 e-service email analysis, renaming, and downloads per month
7-day retention (or optional deletion within 24 hours for security)
Intelligent extraction
Anchor date detection
Editable deadlines
Upload e-service emails
Download calendar entries as ICS files to import into your preferred calendar application
Email calendar invites
Forward e-service emails to a custom address for processing
Optional email address @efiling.deadlinepilot.com to add as a secondary email address to the E-Portal for immediate and automatic processing of new filings
Support via email

Premium

$89/year

$108/yr Save $19 vs. monthly

For moderate use

Everything in the free tier with increased limits
10 scheduling orders with calendar invitations per month
25 e-service email analysis, renaming, and downloads per month
30-day retention (or optional deletion within 24 hours for security)

Plus

Automatically email calendar invitations to your team (or download them as ICS files to import into your preferred calendar application)
Forward e-service emails to a custom address for processing
Optional email address @efiling.deadlinepilot.com to add as a secondary email address to the E-Portal for immediate and automatic processing of new filings
Most Popular

Professional

$199/year

$228/yr Save $29 vs. monthly

For busy practitioners

Everything in premium with increased limits
30 scheduling orders with calendar invitations per month
100 e-service email analysis, renaming, and downloads per month
365-day retention (or optional deletion within 24 hours for security)

Plus

Forward e-service emails to a custom address for processing
Optional email address @efiling.deadlinepilot.com to add as a secondary email address to the E-Portal for immediate and automatic processing of new filings

Firm

5 seat minimum
$9/month, per seat
Everything in professional with no limits
Unlimited scheduling orders with calendar invitations per month
Unlimited e-service email analysis, renaming, and downloads per month
Unlimited retention (or optional deletion within 24 hours for security)

Plus

Dedicated account manager
Custom onboarding and training
Your firm's branding
Enterprise SSO login (optional)

See our Privacy Policy.

Stop manually entering court deadlines

Deadline Pilot is opening to a limited group of Florida litigation firms. Request an invitation — free for your first 3 orders a month when we open.