Comparison
planning-with-files vs obsidian-Smart2Brain
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.
Markdown twin · planning-with-files alternatives · obsidian-Smart2Brain alternatives
GraphCanon updated today
Trust & integrity
| Signal | planning-with-files | obsidian-Smart2Brain |
|---|---|---|
| Maintenance | Very active (1d since push) As of today · github_public_v1 | Very active (0d since push) As of today · github_public_v1 |
| Provenance | Not a fork · Personal account As of today · github_public_v1 | Not a fork · Organization account As of today · github_public_v1 |
| Security (OSV) | No lockfile As of today · none | No lockfile As of today · none |
Tagline
- planning-with-files
- Persistent file-based planning for AI coding agents
- obsidian-Smart2Brain
- An Obsidian plugin to interact with your privacy focused AI-Assistant
Stars
- planning-with-files
- 25k
- obsidian-Smart2Brain
- 1.2k
Forks
- planning-with-files
- 2.1k
- obsidian-Smart2Brain
- 105
Open issues
- planning-with-files
- 5
- obsidian-Smart2Brain
- 50
Language
- planning-with-files
- Python
- obsidian-Smart2Brain
- TypeScript
Adopt for
- planning-with-files
- A tool designed for providing persistent file-based planning in long-running AI coding tasks.
- obsidian-Smart2Brain
- 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
- planning-with-files
- -
- obsidian-Smart2Brain
- -
Runtime
- planning-with-files
- -
- obsidian-Smart2Brain
- -
License
- planning-with-files
- MIT
- obsidian-Smart2Brain
- MIT
Last pushed
- planning-with-files
- Jul 9, 2026
- obsidian-Smart2Brain
- Jul 11, 2026
Categories
- planning-with-files
- AI Agents, Developer Tools
- obsidian-Smart2Brain
- AI Agents, Developer Tools
Trust and health
Days since push
- planning-with-files
- 1d
- obsidian-Smart2Brain
- 0d
Open issues (now)
- planning-with-files
- 5
- obsidian-Smart2Brain
- 50
Owner type
- planning-with-files
- User
- obsidian-Smart2Brain
- Organization
Full report
- planning-with-files
- Trust report
- obsidian-Smart2Brain
- Trust report
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.
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.
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 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.
Explore
Sources
Every stat on this page traces to a dated GitHub sync, license file, enrichment field, or trust scan.
- GitHub stars (OthmanAdi/planning-with-files) · observed Jul 11, 2026
- GitHub forks (OthmanAdi/planning-with-files) · observed Jul 11, 2026
- Last push (OthmanAdi/planning-with-files) · observed Jul 9, 2026
- License file (MIT) · observed Jul 11, 2026
- Decision facts (enrichment) · observed Jul 11, 2026
- Trust scan (lockfile / OSV) · observed Jul 11, 2026
- GitHub stars (your-papa/obsidian-Smart2Brain) · observed Jul 11, 2026
- GitHub forks (your-papa/obsidian-Smart2Brain) · observed Jul 11, 2026
- Last push (your-papa/obsidian-Smart2Brain) · observed Jul 11, 2026
- License file (MIT) · observed Jul 11, 2026
- Decision facts (enrichment) · observed Jul 12, 2026
- Trust scan (lockfile / OSV) · observed Jul 11, 2026
GitHub stars on cards: planning-with-files 25k · obsidian-Smart2Brain 1.2k (synced Jul 11, 2026).
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 and obsidian-Smart2Brain alternatives (planning-with-files markdown twin, obsidian-Smart2Brain markdown twin), 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 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; obsidian-Smart2Brain trust report.