search_files

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

Annotations already declare readOnlyHint, idempotentHint, and non-destructive, so safety is covered. The description adds useful behavioral context beyond that: content coverage (PDFs page-by-page, photos, audio/video transcripts with timestamps), the return shape (match location, excerpt, segment_id), and the meaning of the 'weaker_match' flag. It does not discuss ranking limits beyond the 'weaker_match' hint or pagination behavior.

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 routing instruction ('use it first'/'they aren't on this machine') is front-loaded, followed by scope, then return format. No sentence is filler – each adds a distinct piece of information the agent can act on.

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?

There is no output schema, so the description's prose about return contents (match location, excerpt, segment_id, weaker_match) carries the burden and does so adequately. Combined with explicit usage guidance, nothing essential is missing for correct invocation.

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 100%, so all four parameters already have definitions, establishing a baseline of 3. The description adds a little interpretive value by clarifying that the query works both semantically ('by meaning') and as exact words/codes, which helps frame how to phrase a query.

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?

States a specific verb and resource ('Find the user's Mac files by content') and immediately scopes it as index-based semantic + keyword search. It explicitly distinguishes itself from the terminal/local file tools and from browse_file-style siblings by naming its role as the entry point.

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?

Gives an explicit rule: 'use it first for any question about the user's files' and explains why the alternatives fail ('they aren't on this machine'). It also names read_passage as the follow-up consumer of the returned segment_id, routing the agent across siblings without ambiguity.

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