Organize Documents by Content

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

The description adds some behavioral context beyond the annotations by mentioning dry_run to preview changes, implying the actual run moves/reorganizes files. However, it does not explicitly state that files will be moved or that the operation can be destructive, despite destructiveHint=true. The dry_run tip indirectly addresses safety, but it lacks explicit disclosure of the side effects (e.g., permanent directory restructuring).

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 concise and well-structured: a single opening sentence states the purpose, followed by two sentences explaining strategies and a clear tip about dry_run. It front-loads the main action and uses no filler, making it easy to scan.

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?

Given the tool's complexity (7 parameters, 2 strategies, destructive), the description covers the core behavior and provides a safety tip (dry_run). It does not explain all parameters (e.g., recursive, create_shortcuts, response_format), but those are documented in the schema. It lacks explicit mention of return values or undo options, but no output schema exists. The main gap is not explicitly stating the destructive nature beyond the annotation, but the dry_run tip mitigates this. Overall, it is fairly complete for an agent to decide when and how to use it.

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 coverage is 86%, so most parameters are already documented. The description adds significant value for the strategy parameter by detailing file types for topic (PDF, DOCX, TXT, MD, RTF, ODT) and the heuristic for project (shared name tokens, content terms, identifiers). This goes beyond the schema's brief enum description, adding meaningful usage semantics.

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 organizes files based on content analysis, and distinguishes between two strategies (topic and project) with specific file types and grouping logic. This differentiates it from sibling tools like organize_by_type or organize_photos by emphasizing content-based grouping.

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?

It provides clear usage context: strategy='topic' for documents, strategy='project' for mixed file types, and a direct tip to use dry_run=true for previewing changes. While it doesn't explicitly mention when to use this tool over other organizers, the content-based focus and strategy options give sufficient guidance. No exclusions are stated, but the core purpose is clear.

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