--- title: "planning-with-files vs obsidian-Smart2Brain" type: "comparison" canonical_url: "https://www.graphcanon.com/compare/othmanadi-planning-with-files-vs-your-papa-obsidian-smart2brain" tools: ["othmanadi-planning-with-files", "your-papa-obsidian-smart2brain"] --- # planning-with-files vs obsidian-Smart2Brain *GraphCanon updated Jul 12, 2026* ## Verdict Pick planning-with-files if a tool designed for providing persistent file-based planning in long-running AI coding tasks; pick obsidian-Smart2Brain if a TypeScript-based Obsidian plugin that enhances the note-taking platform by integrating a privacy-focused AI assistant. This integration supports embeddings and is compatible with frameworks like Ollama. [planning-with-files](https://github.com/OthmanAdi/planning-with-files) reports 25k GitHub stars, 2.1k forks, and 5 open issues, last pushed Jul 9, 2026. [obsidian-Smart2Brain](https://github.com/your-papa/obsidian-Smart2Brain) has 1.2k stars, 105 forks, and 50 open issues, last pushed Jul 11, 2026. Figures are from public GitHub metadata via [planning-with-files's repository](https://github.com/OthmanAdi/planning-with-files) and [obsidian-Smart2Brain's repository](https://github.com/your-papa/obsidian-Smart2Brain). | | [planning-with-files](/tools/othmanadi-planning-with-files.md) | [obsidian-Smart2Brain](/tools/your-papa-obsidian-smart2brain.md) | | --- | --- | --- | | Tagline | Persistent file-based planning for AI coding agents | An Obsidian plugin to interact with your privacy focused AI-Assistant | | Stars | 25,184 | 1,199 | | Forks | 2,128 | 105 | | Open issues | 5 | 50 | | Language | Python | TypeScript | | Adopt for | A tool designed for providing persistent file-based planning in long-running AI coding tasks. | A TypeScript-based Obsidian plugin that enhances the note-taking platform by integrating a privacy-focused AI assistant. This integration supports embeddings and is compatible with frameworks like Ollama. | | Persona | - | - | | Runtime | - | - | | License | MIT | MIT | | Categories | AI Agents, Developer Tools | AI Agents, Developer Tools | ## Trust and health _Sourced signals - not a safety guarantee. No winner column._ | | [planning-with-files](/tools/othmanadi-planning-with-files.md) | [obsidian-Smart2Brain](/tools/your-papa-obsidian-smart2brain.md) | | --- | --- | --- | | Days since push | 1d | 0d | | Open issues (now) | 5 | 50 | | Owner type | User | Organization | | Full report | [trust report](/tools/othmanadi-planning-with-files/trust.md) | [trust report](/tools/your-papa-obsidian-smart2brain/trust.md) | ## Decision facts: planning-with-files - **Pricing:** freemium - Freely available under MIT License; community-supported. - **Adopt for:** A tool designed for providing persistent file-based planning in long-running AI coding tasks. ## Decision facts: obsidian-Smart2Brain - **Adopt for:** A TypeScript-based Obsidian plugin that enhances the note-taking platform by integrating a privacy-focused AI assistant. This integration supports embeddings and is compatible with frameworks like Ollama. ## Choose when ### Choose planning-with-files if… - planning-with-files is primarily Python; obsidian-Smart2Brain is TypeScript. - Pricing: Freely available under MIT License; community-supported.. - Tags unique to planning-with-files: agent-skills, codex, coding-agent, claude-code. - - When your coding agent needs to retain plans across sessions without context loss. ### Choose obsidian-Smart2Brain if… - obsidian-Smart2Brain is primarily TypeScript; planning-with-files is Python. - Tags unique to obsidian-Smart2Brain: embeddings, ai, rag, chatgpt. - You are using Obsidian for note-taking and want to enhance your digital knowledge repository in a privacy-conscious manner, leveraging smart interaction features. ## When NOT to use planning-with-files - - When you do not need persistent storage for plans, such as short tasks where context is unlikely to be lost. - - For projects that strictly prohibit the use of external file storage for tracking progress due to security concerns. - - If your workflow heavily relies on in-memory planning strategies that are more suitable than disk-based solutions. ## When NOT to use obsidian-Smart2Brain - You require real-time updates from public AI services like ChatGPT directly within your notes, as Smart2Brain emphasizes a private AI experience. - If your workflow does not involve managing extensive digital knowledge repositories or if you do not use Obsidian for note-taking purposes. ## Common questions ### What is the difference between planning-with-files and obsidian-Smart2Brain? planning-with-files: Persistent file-based planning for AI coding agents. obsidian-Smart2Brain: An Obsidian plugin to interact with your privacy focused AI-Assistant. See the comparison table for live GitHub stats and shared categories. ### When should I choose planning-with-files over obsidian-Smart2Brain? Choose planning-with-files over obsidian-Smart2Brain when planning-with-files is primarily Python; obsidian-Smart2Brain is TypeScript; Pricing: Freely available under MIT License; community-supported.; Tags unique to planning-with-files: agent-skills, codex, coding-agent, claude-code; - When your coding agent needs to retain plans across sessions without context loss. ### When should I choose obsidian-Smart2Brain over planning-with-files? Choose obsidian-Smart2Brain over planning-with-files when obsidian-Smart2Brain is primarily TypeScript; planning-with-files is Python; Tags unique to obsidian-Smart2Brain: embeddings, ai, rag, chatgpt; You are using Obsidian for note-taking and want to enhance your digital knowledge repository in a privacy-conscious manner, leveraging smart interaction features. ### When should I avoid planning-with-files? - When you do not need persistent storage for plans, such as short tasks where context is unlikely to be lost. - For projects that strictly prohibit the use of external file storage for tracking progress due to security concerns. - If your workflow heavily relies on in-memory planning strategies that are more suitable than disk-based solutions. ### When should I avoid obsidian-Smart2Brain? You require real-time updates from public AI services like ChatGPT directly within your notes, as Smart2Brain emphasizes a private AI experience. If your workflow does not involve managing extensive digital knowledge repositories or if you do not use Obsidian for note-taking purposes. ### Is planning-with-files or obsidian-Smart2Brain more popular on GitHub? planning-with-files has more GitHub stars (25,184 vs 1,199). Stars measure visibility, not whether either tool fits your constraints. ### Are planning-with-files and obsidian-Smart2Brain open source? Yes - both are open-source projects on GitHub (planning-with-files: MIT, obsidian-Smart2Brain: MIT). ### Where can I find alternatives to planning-with-files or obsidian-Smart2Brain? GraphCanon lists graph-backed alternatives at [planning-with-files alternatives](/tools/othmanadi-planning-with-files/alternatives) and [obsidian-Smart2Brain alternatives](/tools/your-papa-obsidian-smart2brain/alternatives) ([planning-with-files markdown twin](/tools/othmanadi-planning-with-files/alternatives.md), [obsidian-Smart2Brain markdown twin](/tools/your-papa-obsidian-smart2brain/alternatives.md)), ranked by typed relationship edges rather than popularity votes. ### Is there a machine-readable version of this comparison? Yes. The markdown twin at [this comparison](/compare/othmanadi-planning-with-files-vs-your-papa-obsidian-smart2brain.md) mirrors this page for agents and LLM crawlers, with the same stats table and FAQ answers. ### Which is better maintained, planning-with-files or obsidian-Smart2Brain? planning-with-files: Very active. obsidian-Smart2Brain: Very active. Compare maintenance labels, days since push, and release cadence in the trust section below - stars alone do not measure maintenance. ### Where are the full trust reports for planning-with-files and obsidian-Smart2Brain? GraphCanon publishes per-repo trust reports with dated maintenance, provenance, and scan summaries: [planning-with-files trust report](/tools/othmanadi-planning-with-files/trust); [obsidian-Smart2Brain trust report](/tools/your-papa-obsidian-smart2brain/trust). --- **Machine-readable endpoints** - JSON: [`/api/graphcanon/graph?tool=othmanadi-planning-with-files`](/api/graphcanon/graph?tool=othmanadi-planning-with-files) - LLM index: [/llms.txt](/llms.txt) - Full corpus: [/llms-full.txt](/llms-full.txt) _GraphCanon - The knowledge graph for AI development. https://www.graphcanon.com/_