markdown_outline

Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

With no annotations provided, the description carries the full burden of behavioral disclosure. It adds critical context such as path requirements (absolute, no URL-encoding, must exist) and output format defaults. While it doesn't mention error handling or side effects, the read-only nature is implied and the provided constraints are valuable.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

The description is well-structured with separate sections for the core one-liner, usage guidelines, path requirements, example paths, args, and returns. It is somewhat lengthy but every section adds needed information; the example paths are a minor addition but not wasteful.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

The description covers the tool's purpose, usage boundaries, parameter semantics, path constraints, and return format. It doesn't detail the exact structure of the returned outline, but the 'Returns' line gives a minimal overview. For a relatively simple file-reading tool, this is sufficiently complete.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema description coverage is 0%, but the description compensates fully with an Args section that explains each parameter: paths (list of absolute Markdown paths) and output_format (valid values 'json' or 'markdown', default behavior). This goes well beyond the bare schema, including allowed values and defaults.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

The description clearly states the tool returns an outline for each Markdown file, listing headings, levels, and line numbers. It uses a specific verb and resource, and the inclusion of 'Markdown' distinguishes it from sibling tools like python_outline and dir_tree.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

Explicit agent usage guidelines are provided, stating when to use the tool (extract/display Markdown structure, navigation, summary, documentation analysis) and when not to use it (non-Markdown files or reading full content). This gives clear exclusions and context without explicitly naming alternatives.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.