Managing calendars is getting harder. Court rules change constantly. Attorneys work remotely. And missing one deadline can cost you everything.
But here’s what hasn’t changed:
If you have the right calendar system, you can still manage complex schedules, automate court deadlines, and keep your entire team synchronized.
Not by using basic calendar apps, but by investing in tools that understand legal requirements, sync across platforms, and protect your practice from malpractice claims.
The best multi-attorney calendar tools help you do exactly that:
- Automatically calculate court deadlines across thousands of jurisdictions
- Sync seamlessly between Outlook, Google Calendar, and mobile devices
- Share calendars across your team without compromising security
- Get notified instantly when court rules change
These are the tools successful medium-sized firms use to manage hundreds of matters without missing deadlines.
(Most with 10-50 attorneys handling complex litigation)
The best part?
These tools actually get better as your firm grows. No matter your practice area or jurisdiction.
My Top Multi-Attorney Calendar Tools for 2025
- LawToolBox: Best for Microsoft 365 integration and automated court rules
- Clio: Best for comprehensive practice management with court rules integration
- Smokeball: Best for automated time tracking with calendar sync
LawToolBox
Best for firms using Microsoft 365 who need automated court rules and deadline calculations
Pricing: 2-9 users: $42/month per user; 10-19 users: $40/month per user; 20-79 users: $30/month per user; 80+ users: $22/month per user
LawToolBox is the industry-leading court ruleset provider that powers most online law practice platforms. It’s built directly into Microsoft 365, making it perfect for firms already using Outlook, Teams, and SharePoint.
I use LawToolBox differently than other calendar tools.
I use it specifically for court deadline automation. And LawToolBox REALLY excels in eliminating the manual work and risk of calculating complex deadlines.
Automated Court Rules for 50 States
LawToolBox automates rules-based calendaring for thousands of state and federal courts then syncs to your calendar in seconds.
This isn’t just basic calendar management. LawToolBox has rule sets for all 50 states in any practice area with rules-based calendaring, including Local, State, Federal, Appellate, Bankruptcy and other specialty rules.
When you file a motion, you simply select the jurisdiction and add a “trigger date,” such as a trial or deposition. Then in just one click, the relevant deadlines will be automatically added to your calendar.
For medium-sized firms handling litigation across multiple jurisdictions, this means you can trust that every deadline is calculated correctly, whether you’re dealing with federal civil procedure or local court rules in small counties.
Centralized Multi-Attorney Management
Save hours managing deadlines with a centralized deadline management solution that automates rules-based calendaring for 50 states.
The platform allows you to assign specific deadlines to different users. For example, you can assign “discovery deadlines” to one paralegal and “summary judgment deadlines” to a senior associate. LawToolBox serves as a central place where everyone on a case can see what’s done and what’s coming up.
Update internal Outlook calendars or external team member Google, iCal, Lotus Notes calendars, and case management platforms that two-way sync with Outlook.
This centralized approach means your docketing team can manage calendars for multiple attorneys from one dashboard, while each attorney still sees their personalized calendar in their preferred format.
Automatic Court Rule Updates
LawToolBox has a dedicated team of attorneys monitoring daily for any changes to court rules so you can rest easy knowing your deadlines are always up to date and accurate.
When court rules change, the system automatically updates your existing deadlines and notifies affected users. This is crucial for medium-sized firms that might not have dedicated docketing staff monitoring rule changes across multiple jurisdictions.
The system also provides links to all applicable court rules for each deadline, so attorneys can quickly reference the authority behind any calculated date.
Pros & Cons
| Pros | Cons |
|---|---|
| Automatically calculate rules-based deadlines and sync to any calendar, saving you time while ensuring you never miss a deadline | Some users find the interface confusing with special codes that make no sense |
| Integrates directly with Microsoft 365 for easy deployment, training, and use | Customer service can be slow to resolve complex technical issues |
| Covers more than 2,500 jurisdictions in the United States | Limited customization options for deadline descriptions |
LawToolBox Alternative: CompuLaw
CompuLaw is Aderant’s leading legal calendaring and docketing solution that covers over 2,500 jurisdictions. It’s particularly strong for larger firms that need enterprise-level docketing capabilities.
However, LawToolBox’s direct integration with Microsoft 365 and more transparent pricing make it more accessible for medium-sized firms. CompuLaw requires custom pricing and is typically more expensive for firms under 100 attorneys.
Clio
Best for comprehensive practice management with integrated court rules and team collaboration
Pricing: EasyStart: $49/month per user; Essentials: $79/month per user; Advanced: $109/month per user; Complete: $139/month per user
Clio is approved by more than 100 bar associations and law societies worldwide, including all 50 US state bars. It offers the most comprehensive practice management platform with powerful calendaring features built specifically for legal teams.
Clio acquired CalendarRules in 2021 to provide automated court rules-based calendaring, making it a true all-in-one solution for medium-sized firms.
Rules-Based Calendaring with Court Rules Integration
Use Clio’s law firm calendaring software to create events automatically based on rules and deadlines from hundreds of U.S. courts. Stay on top of filing deadlines, case milestones, court dates, and more.
Clio’s Court Rules feature provides automated rules-based calendaring for your firm from a library of court rules across 50 US states and 2,300 jurisdictions. It’s also available in Canada for Federal Court, British Columbia Supreme Court, and Ontario Court of Justice.
The system automatically creates court deadlines based on local rules. This ensures you never miss filing deadlines for any type of case, from simple contract disputes to complex commercial litigation.
Multi-Attorney Team Collaboration
Each user in your firm can create, share, and view calendars for firm-wide meetings, intake appointments, or case-specific dates.
The calendar system allows you to organize events by case, attorney, or practice area. You can easily turn specific calendars on and off, which helps manage information overload when attorneys work on multiple matters.
Send calendar invites and automated reminders to clients through text and receive confirmation of their attendance. This keeps clients informed while reducing no-shows.
Seamless Integration and Mobile Access
Connect with Microsoft Outlook or Google Calendar to automatically keep your calendar current, no matter where you update it.
Every calendar change syncs in real-time across all platforms. Whether an attorney updates their calendar in Clio, Outlook, or Google Calendar, everyone sees the same information immediately.
Access your calendar on the go from Clio’s mobile app. Update case milestones, confirm client appointments by text message, and automatically schedule deadlines based on court rules.
Pros & Cons
| Pros | Cons |
|---|---|
| Approved by more than 100 bar associations and law societies worldwide | Higher cost when you add multiple modules for full functionality |
| Create events for cases automatically, based on rules and deadlines from hundreds of U.S. courts | Cannot assign one task to multiple people |
| Comprehensive practice management beyond just calendaring | Can be overwhelming for firms that only need calendaring |
Clio Alternative: MyCase
MyCase provides comprehensive legal calendaring with direct LawToolBox integration for court rules. It offers similar features at a lower price point, starting at $49/month per user.
However, Clio’s broader ecosystem of features and superior integration capabilities make it more scalable for growing medium-sized firms that need more than just calendaring.
Smokeball
Best for automated time tracking with intelligent calendar sync and workflow automation
Pricing: Bill: $39/month per user; Boost: $49/month per user; Grow: $99/month per user; Prosper+: $219/month per user
Smokeball offers a hybrid desktop and cloud-based solution with exceptional Microsoft Outlook integration. It’s particularly strong for firms that want automated time tracking combined with sophisticated calendaring.
Smokeball’s Activity Intelligence feature automatically tracks time as you work in Smokeball, Word, or Outlook, making it perfect for medium-sized firms focused on maximizing billable hours.
Intelligent Two-Way Calendar Sync
Every event updated in both Smokeball and Outlook in real time. Create events tied to a matter or schedule general firm appointments.
Smokeball offers two-way calendar sync with Microsoft Outlook, so events created or updated in either system stay in sync automatically. This eliminates the double data entry that plagues many firms.
You can create calendar events that are linked to specific matters, giving you clear visibility over court dates, appointments, and deadlines for each case. This matter-specific organization helps attorneys stay focused on the right priorities.
Automated Deadline Calculation with LawToolBox Integration
Automatically calculate deadlines based on court rules and filing dates. Sync all key litigation dates into your Smokeball calendar.
Smokeball integrates directly with LawToolBox to provide automated court deadline calculations within the platform. You can automatically calculate all deadlines related to your case and sync to any calendar in seconds.
This integration eliminates the manual work of calculating complex court deadlines while ensuring everything stays organized within your matter management system.
Team Calendar Management with Smart Reminders
Set reminders for yourself or your team and view multiple calendars at once. Group events into separate calendars, such as one for court dates.
The system allows you to create smart reminders for any event and assign them to yourself or other staff, helping your team stay on top of important dates.
Schedule firm wide events such as team meetings, holidays, or room bookings. Multiple attorneys can share calendars while maintaining visibility into their individual schedules.
Pros & Cons
| Pros | Cons |
|---|---|
| Automatically capture every billable minute with Activity Intelligence | The cost of support staff licenses can be prohibitive for larger teams |
| Two-way Outlook sync ensures every appointment stays updated in real time | Some users experience occasional sync issues that require technical support |
| Matter-linked events connect every date to the right case for full visibility | Limited integration options compared to other platforms |
Smokeball Alternative: PracticePanther
PracticePanther offers similar practice management features with calendar integration and LawToolBox support. It provides more comprehensive reporting and analytics features.
However, Smokeball’s automatic time tracking and tight Outlook integration make it more efficient for firms focused on maximizing billable hours and productivity.
Other Tools Medium-Sized Firms Use for Calendar Management
Managing complex litigation calendars requires more than just scheduling software.
At successful medium-sized firms, I see additional tools that complement their main calendar system:
- Microsoft Teams for secure video conferencing and collaborative case discussions
- PACER integration tools for automatic docket monitoring and ECF notifications
- Mobile apps for calendar access during court appearances and client meetings
- Document management systems that link deadlines to relevant case documents
There are obviously many other legal calendar options available. But these are the ones I recommend evaluating first for medium-sized firms. A comprehensive solution that integrates with your existing technology stack usually makes the most sense, as it eliminates the complexity of managing multiple systems. But beyond that, you should prioritize tools that can scale with your firm’s growth and handle the increasing complexity of multi-attorney practices.
