sideOS vs Willow
sideOS and Willow are both personal productivity tools. sideOS is aimed at freelancers and developers, while Willow is aimed at freelancers and small businesses. Only Willow has a free plan.
Voice-driven Mac agent in the notch with local dictation and meetings
AI voice dictation and writing agent that works in any app
| Pricing | Paid | Freemium · $15 |
| Starting price | Not published | $15/mo |
| Free plan | No | Yes |
| Free trial | — | — |
| Built for | Freelancers, Developers, Small businesses | Freelancers, Small businesses, Enterprise, Creators |
| Platforms | macos | macos, windows, ios |
| Country | — | US · 2025 |
| Rating | — | — |
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).
Choose Willow if
Professionals and developers who write a lot of email, chat messages and AI prompts on Mac, Windows or iPhone and want to speak instead of type.
- Works system-wide, so no per-app plugins are needed
- Cleans and formats text instead of producing raw transcripts
- Wally and style memory adapt drafts to email, Slack or prompts
Look elsewhere if: Android users or people who mainly want grammar and style polishing of text they type themselves (Grammarly, Wordtune).
sideOS vs Willow pricing
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
Willow
- Basic$0Frontier Mini dictation model, 20 Scribe uses per week
- Pro$15/moPer user; Frontier Pro model, unlimited Scribe; $12 billed annually
- Business$35/moEnforced zero data retention, HIPAA, admin; $28 billed annually
- EnterpriseCustomSSO/SAML, invoice billing, MSA and DPA, usage API
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
Willow · Key features
- Hotkey voice dictation into any text field on Mac, Windows and iPhone
- Automatic filler removal, punctuation and app-aware formatting
- 100+ languages with switching, plus whisper and offline modes
- Auto-learning dictionary for names, product terms and abbreviations
- Scribe drafts emails and replies from a spoken brief or rewrites highlighted text
- Wally chat agent that iterates on drafts and learns your style per app
Cons
- No Android app yet; it is listed as coming soon
- Free plan uses a weaker model and caps Scribe at 20 uses a week
- Enforced zero data retention and HIPAA require the $35 Business plan
sideOS vs Willow: FAQ
Do sideOS and Willow have a free plan?
sideOS has no free plan. Willow has a free plan.