Kai vs sideOS
Kai and sideOS are both AI assistants tools. Kai is aimed at freelancers and small businesses, while sideOS is aimed at freelancers and developers. Only Kai has a free plan.
AI executive assistant for email, meetings, calendar and tasks
Voice-driven Mac agent in the notch with local dictation and meetings
| Pricing | Paid · $20 | Paid |
| Starting price | $20/mo | Not published |
| Free plan | Yes | No |
| Free trial | — | — |
| Built for | Freelancers, Small businesses, Enterprise | Freelancers, Developers, Small businesses |
| Platforms | web, macos, android | macos |
| Country | CH | — |
| Rating | — | — |
Choose Kai if
Founders, executives and consultants who want one assistant across email, meetings, calendar and tasks with approval before every action.
- Never sends or deletes without your confirmation
- No meeting bot joins your calls
- Free trial with no card and no time limit
Look elsewhere if: People who only need a fast email client or a meeting notepad (Superhuman, Granola).
Choose sideOS if
Mac professionals who want a private voice agent, dictation and meeting notes in one app they pay for once.
- One-time licence with all future updates and no subscription
- No account and no sideOS server between you and the model
- Dictation and meeting transcription stay on the Mac
Look elsewhere if: Windows or mobile users and teams that need shared meeting notes or admin controls (Granola, Raycast).
Kai vs sideOS pricing
Kai
- Free trial$0One-time allowance, all features, no card, no time limit
- Base$20/moPer seat; base monthly allowance
- Pro$50/moPer seat; 5x Base allowance, includes Morgen Pro
- Ultra$100/moPer seat; 10x Base allowance, includes Morgen Pro
sideOS
- Lifetime licence$89.90One-time; one Mac at a time, every future update included
- AI model usageVariesPaid to your own provider, about 2 to 5 cents per command
Kai · Key features
- Botless meeting capture with live transcripts
- Meeting summaries with owners, action items and drafted recap emails
- Email triage into needs reply, FYI and waiting for reply
- Reply drafts in your own writing style and follow-up nudges
- Unified Google and Outlook calendar timeline with a daily brief
- AI-ranked task list filled from meetings and email
Cons
- Usage allowances are not published in absolute terms
- Hitting the monthly allowance pauses work until you upgrade
- Full two-sided call capture needs the Mac app
sideOS · Key features
- Hold-to-talk agent that reads the screen, clicks, types and runs AppleScript
- On-device dictation into any app in 62 languages at no extra cost
- Meeting recording for Zoom, Meet and Teams with on-device Whisper and speakers
- Background tasks with web search, file access and approved shell commands
- Reminders that can complete a task before they fire
- One-click MCP connections for Gmail, Calendar, Notion, Slack and GitHub
Cons
- Apple Silicon Macs with macOS 14 or later only
- Agent use adds API costs unless you run a local model
- No free trial or refund window stated on the site
Kai vs sideOS: FAQ
Do Kai and sideOS have a free plan?
Kai has a free plan. sideOS has no free plan.