Sunsama Timeboxing 2.0

Overview

Timeboxing 2.0 is Sunsama's upcoming feature that represents a significant evolution from manual time blocking to AI-assisted automatic scheduling. This feature is slated for release later in 2026.

What's New

Timeboxing 2.0 will automatically:

• Populate your calendar with tasks from your to-do list
• Consider task priorities when scheduling
• Account for calendar availability and existing commitments
• Adjust schedules dynamically as priorities change

Context: Current Timeboxing in Sunsama

Currently, Sunsama offers manual timeboxing where users:

• Drag and drop tasks onto their calendar
• Manually assign time blocks to tasks
• Create calendar events for each task
• Update manually when schedules change

Competitive Landscape

This feature brings Sunsama closer to AI-powered competitors like:

• Motion (which already offers automatic AI scheduling)
• Reclaim.ai (priority-based automatic scheduling)
• FlowSavvy (automatic time blocking for individuals)

Significance

The absence of AI features has been a notable gap for Sunsama as of early 2026, with competitors increasingly offering intelligent scheduling. Timeboxing 2.0 addresses this competitive pressure while maintaining Sunsama's mindful, intentional approach to productivity.

Pricing Context

At $25/month with no free tier, Sunsama is one of the most expensive individual productivity tools. Timeboxing 2.0 may help justify this premium by adding automation that saves planning time.

Expected Benefits

• Reduced time spent on daily planning
• More realistic daily schedules
• Automatic adjustments when plans change
• Better balance between available time and committed tasks