search_files

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

With no annotations present, the description carries the burden of behavioral disclosure. It does this well by explaining result scoping, default date behavior, UTC interpretation, and the dialog-by-dialog scanning caveat. It also lists the exact per-match return fields, which goes beyond what is structurally required.

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 front-loaded with the core purpose, followed by useful parameter details and a return value list. Each sentence adds meaningful information without unnecessary fluff, though the parameter explanations could be more visually structured.

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 has five optional parameters and an output schema, the description covers the most critical behavioral aspects: file type semantics, date range behavior, and global search limitations. The main gaps are the lack of explanation for query and limit, but the output schema and parameter names partly mitigate this.

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?

The description provides rich semantics for file_type and since_date, including allowed values, exclusions, defaults, and timezone handling. However, chat, query, and limit are left entirely unexplained, and schema description coverage is 0%, so the description only partially compensates for the missing parameter documentation.

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 opening line 'Find messages carrying files, globally or in one chat' uses a specific verb and defines the resource and scope. It clearly references search_messages as a related sibling but does not explicitly distinguish when to use this tool versus the alternative for text-based search.

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 gives contextual usage guidance, such as the global-search caveat and the default 7-day window, but does not explicitly state when to prefer search_files over search_messages or when to use download_file after finding files. Usage is implied rather than explicitly contrasted with alternatives.

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