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Chunk vs Checkpoint64

A side-by-side comparison built from both listings. Blank cells mean the company has not given that detail; we never guess.

Chunk compared with Checkpoint64
DetailChunk logo ChunkCheckpoint64 logo Checkpoint64
What it doesTime blocking app for Mac with two-way calendar sync and AI integration Automatic cloud backup and full version history for PC game saves
StageNot given Startup
FoundedNot given 2026
Based inNot given GB
Pricing modelPaid Freemium
PricingFree trial for 7 days (no credit card required). Lifetime License: $29.99 USD (full access for 2 Macs, all current features and future updates included). Family Package: $59.99 USD (full access for up to 6 Macs, all current features and future updates included). Coming soon: Chunk for iPhone at $8.9 Free: 20 MiB storage, one personal space, one team, full version history, co-op locks included. Lifetime: €10 one-time purchase, 1 GiB storage per space, up to 3 teams, share codes for 15 read-only fans. Pro: €45 one-time purchase, 5 GiB storage per space, up to 5 teams, 25 seats per team minimum, u
Key features
  • Two-way calendar sync with Apple Calendar, Google Calendar, and Outlook
  • Integration with Apple Reminders and custom task lists
  • Local Claude AI assistant for natural language scheduling via MCP
  • Menu bar panel with global keyboard shortcut (Cmd+/)
  • Live countdown timer and fullscreen alerts
  • Recurring task templates and reusable daily plans
  • Multiple schedule views (day, week, month) with timeline compression
  • Cross-device sync across Macs via iCloud
  • Analytics dashboard tracking planned hours, completions, and follow-through
  • Schedule export as PDF or CSV
  • Automatic background backups every 60 seconds
  • Full version history with one-click restore
  • Server-enforced co-op locks to prevent simultaneous uploads
  • Deduplicated uploads for changed files only
  • Presets for 450+ games and 7 emulators
  • Shared activity logbook for teams
  • Read-only share codes for community worlds
  • Checkpoint Connect for peer-to-peer server hosting without port forwarding
  • Full controller navigation including Steam Deck
What makes it different
  • Built for ADHD users and focus-first workflows with minimal friction
  • One-time $29.99 purchase with no subscription or recurring fees
  • All data stored locally on Mac; never sent to company servers
  • Local Claude AI integration that runs entirely on device
  • Menu bar access with fullscreen floatability while maintaining focus
  • Covers emulators, modded installs, and GOG copies that Steam Cloud does not support
  • Maintains full version history unlike Steam Cloud which syncs broken saves
  • Pay-once lifetime plan with no subscription required
  • Only uploads files that changed to minimize bandwidth and storage
  • Built by solo developer who lost 200-hour Factorio base
Free planNot given Not given
Open sourceNot given Not given
PlatformsNot given Not given
Public APINot given Not given
Community votes00
DR (Domain Rating by Ahrefs)29 −1 (down) since last check4 no change since last check
Trust Flow (Majestic)226
Citation Flow (Majestic)3025
Referring domains (Majestic)16311

5 details filled in for both companies.

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