Home/Compare/planning-with-files vs obsidian-Smart2Brain

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

planning-with-files logo

planning-with-files

OthmanAdi/planning-with-files

25kpushed Jul 9, 2026
vs
obsidian-Smart2Brain logo

obsidian-Smart2Brain

your-papa/obsidian-Smart2Brain

1.2kpushed Jul 11, 2026

Trust & integrity

Signalplanning-with-filesobsidian-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 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.