FileMayor vs Hazel.
Hazel has been the reference Mac file automation tool for over a decade. It is respected, mature, and well-designed. FileMayor is a different shape: AI planning, cross-platform reach, and the Curative Triad safety model. Both tools are good at what they do. They are good at different things.
The decision matrix.
| FileMayor | Hazel | |
|---|---|---|
| Platforms | macOS · Windows · Linux · CLI · PWA | macOS only |
| Pricing | Free · Pro $5.99/mo · Enterprise $24.99/mo | $42 one-time |
| Interaction model | Curative Triad — explain, cure, apply, undo | Rules engine — write IF/THEN rules per folder |
| AI planning | Yes — Gemini 2.0 Flash, optional, local-first | No |
| Rollback | Full session journal · `undo --all` | No native undo for batched moves |
| Watch mode | Yes (Pro) | Yes — core feature |
| Scripting | 14 CLI commands · `--json` everywhere | AppleScript / shell scripts via rules |
| Telemetry | None | None |
| Open source | CLI engine on npm · UI proprietary | Proprietary |
| Best for | Anyone who wants AI + safety + rollback, on any OS | Mac power users who like writing explicit rules |
Mac-only and rules-first.
If you are on macOS exclusively, prefer writing explicit IF/THEN rules over describing intent in natural language, and want a one-time-purchase tool with a long maintenance history, Hazel is excellent. The rules engine is mature, and AppleScript integration unlocks anything macOS exposes.
Cross-platform, AI-planned, reversible.
FileMayor exists for the cases Hazel does not cover well: Windows and Linux machines, teams that want a shared CLI workflow, anyone who would rather describe what they want in plain English than write rules, and anyone who wants the safety net of a full-session undo on every operation.
The Curative Triad — explain → cure → apply — separates planning from execution by design. The Chevza Doctrine ensures that even when an AI proposes a destructive plan, six layers of safety architecture sit between the proposal and your filesystem.
They do not conflict. Hazel can govern a watched folder while FileMayor handles the larger session organization. Many teams run them side by side.