Your projects, milestones
& contacts — all in one place.
CheckStay Pro is a focused macOS app for managing project portfolios, tracking risks, and keeping every stakeholder aligned — with a built-in AI assistant that knows your work.
macOS · Free forever · Pro $49 one-time · Sync from $2.99/mo
CheckStay Pro
Your projects, milestones & contacts — all in one place.
MOC
2 projects
Pinned projects for quick access.
Code
3 projects
Everything you need
Project management, without the overhead
Projects & Milestones
Track every project from kickoff to close. Set milestones with due dates, monitor status at a glance, and keep your portfolio organized with categories and focus pins.
RAID Logs
Capture risks, assumptions, issues, and decisions in structured logs. Rate likelihood and impact, assign owners, and link items to milestones so nothing slips.
Stakeholders & Contacts
Maintain a global contacts library and assign stakeholders per project. Names, orgs, emails, and titles — all accessible from wherever you need them.
Calendar & Outlook
See all your milestones on a unified calendar. Integrate with Microsoft Outlook to pull in events and emails, linking them directly to your projects. Requires Pro.
AI Assistant
A built-in AI bot that sees your projects, remembers your preferences, and takes action — create tasks, log decisions, or ask what's overdue. Bring your own API key. Requires Pro.
Activity Log
Timestamped entries for everything that happens across your projects. Link activities to contacts and emails for a full audit trail.
Pricing
Simple, honest pricing
Free
$0
Forever
- ✓ Up to 3 projects
- ✓ Up to 6 contacts
- ✓ Milestones & checklists
- ✓ RAID logs
- ✓ Bar timeline view
- ✓ Local storage, offline-first
Pro
Most popular$49
One-time purchase
- ✓ Everything in Free
- ✓ Unlimited projects & contacts
- ✓ AI assistant (bring your own key)
- ✓ Gantt & timeline view
- ✓ Outlook & email integration
- ✓ Categories & reports
Sync
$2.99
/mo
or $24/yr — save 33%
- ✓ Encrypted cloud backup
- ✓ Multi-device sync
- ✓ Restore from anywhere
- Add-on for Free or Pro accounts.
Ready to run your projects better?
Start free and upgrade when you need more. One-time purchase, no subscription required for Pro.