Watch Directory

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

Annotations indicate idempotent, non-destructive, and mutating operations. The description adds behavioral context by specifying that schedules are converted to cron expressions and provides conversion rules. However, it does not explain what happens when a directory is already watched, whether existing files are organized immediately, or the persistence of the watch. Given annotations cover the core safety profile, the added schedule-conversion detail justifies a mid-range score.

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 a single paragraph that front-loads the purpose and then provides necessary schedule conversion examples. It is reasonably concise, though the inclusion of four conversion examples extends the length. Each example adds instructional value, but could be trimmed to the most common cases without losing clarity.

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?

For a tool with 6 parameters and no output schema, the description covers the fundamental purpose and schedule conversion but omits details like whether the watch starts immediately, how to verify the watch, or what side effects occur on existing files. Since sibling tools for listing and unwatching exist, an agent might infer these, but explicit mention would improve completeness. The description is adequate but not thorough.

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 83%, so the schema already documents most parameters. The description repeats the cron conversion examples already present in the schedule parameter description, adding no new information for that parameter. It does not elaborate on auto_organize, response_format, max_files_per_run, or min_file_age_minutes, which are already described adequately in the schema. The description adds minimal value beyond what structured fields provide.

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 states a specific action: 'Add a directory to the watch list with a cron-based schedule for automatic organization.' This clearly identifies the verb and resource, and distinguishes it from siblings like unwatch_directory and list_watches. It is unambiguous and directly actionable.

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?

The description implies the tool is for setting up automatic organization on a schedule, which suggests its primary use case. However, it does not explicitly explain when to prefer this tool over alternatives such as scan_directory, organize_files, or preview_organization, nor does it mention any prerequisites or exclusions. The use case is fairly self-evident but lacks explicit routing guidance.

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