Overview
Timeboxing 2.0 represents Sunsama's upcoming evolution from manual time-blocking to AI-assisted scheduling, planned for release in late 2026. This feature will automatically populate users' calendars with tasks based on priorities, deadlines, and availability while maintaining Sunsama's mindful planning philosophy.
Current Status (Mid-2026)
Development Phase
- Feature announced for late 2026 release
- Slated for implementation in Q4 2026
- Currently in development and testing
- Preview access may be available to select users
Market Context
The absence of AI automation has become increasingly noticeable in 2026 as competitors add intelligent scheduling. Timeboxing 2.0 addresses this gap while preserving Sunsama's intentional planning approach.
Planned Features
Automatic Calendar Population
- AI analyzes task list, priorities, and deadlines
- Automatically creates calendar blocks for tasks
- Respects user availability and existing commitments
- Suggests optimal timing based on task requirements
Priority-Based Scheduling
- High-priority tasks scheduled during peak productivity hours
- Deadline-driven placement ensures timely completion
- Balances urgent vs. important work throughout the week
- Prevents overcommitment through capacity analysis
Availability Intelligence
- Identifies open calendar slots for task scheduling
- Respects work hours and personal time boundaries
- Considers meeting patterns and focus time needs
- Adapts to recurring commitments automatically
Philosophy Integration
Mindful Automation
Unlike fully automated systems, Timeboxing 2.0 maintains Sunsama's core principles:
- Users still conduct daily planning rituals
- AI suggestions require user review and approval
- Intentionality remains central to the workflow
- Automation supports rather than replaces human judgment
Behavioral Architecture
Preserves Sunsama's distinctive elements:
- Morning planning ritual sets daily intentions
- Time-blocking flow remains user-guided
- Shutdown routine ensures work-life boundaries
- Mindful task selection over automated assignment
Expected Benefits
Time Savings
- Reduces manual calendar management effort
- Eliminates decision fatigue around task scheduling
- Speeds up daily planning process
- Maintains planning quality with less time investment
Schedule Optimization
- AI identifies optimal task timing based on multiple factors
- Better workload distribution across days and weeks
- Improved deadline management
- Enhanced productivity through intelligent scheduling
Competitive Positioning
- Addresses key feature gap vs. Motion, Reclaim, and other AI planners
- Maintains Sunsama's differentiation through mindful approach
- Attracts users wanting both automation and intentionality
Anticipated Implementation
User Control
- Toggle between manual and AI-assisted timeboxing
- Adjust AI suggestions before committing to calendar
- Override automated placements when needed
- Customize AI behavior through preferences
Learning Capabilities
- System learns from user adjustments over time
- Improves suggestions based on historical patterns
- Adapts to individual work styles and preferences
- Refines timing estimates through actual performance data
Comparison to Competitors
Motion
- Motion fully automates scheduling without user ritual
- Timeboxing 2.0 balances automation with intentional planning
- Sunsama maintains mindful workflow while gaining efficiency
Reclaim.ai
- Reclaim focuses on defending time and habits
- Timeboxing 2.0 emphasizes daily planning integration
- Both offer AI assistance with different philosophies
Release Expectations
Late 2026 Timeline
- Beta testing likely in Q3 2026
- General availability targeted for Q4 2026
- Phased rollout probable for stability
- Existing Sunsama users to receive priority access
Impact Predictions
- May significantly increase Sunsama adoption
- Expected to reduce primary criticism of manual process
- Could attract users from fully-automated competitors
- Likely to influence pricing and plan structures
Current Alternatives
Until Timeboxing 2.0 launches, Sunsama users can:
- Continue with current manual timeboxing
- Use AI-assisted planning in complementary tools
- Maintain the proven daily planning ritual
- Leverage Sunsama's existing integration ecosystem
