search

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

With no annotations at all, the description carries the full burden and does it well: it discloses case-insensitivity, in-word matching, newest-first ordering, one short snippet per hit, and that total_items signals truncation. It also adds a prompt-injection warning about untrusted school content, which is high-value behavioral context; only permission/seen-state behavior is left unexplained.

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?

Front-loaded with the core action and matching rules, then result shape, then usage, then the safety note — a logical progression with little waste. The untrusted-content sentence is long but earns its place as a security instruction.

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?

With no output schema and no annotations, the description still covers ordering, snippet shape, and the total_items truncation signal, which is what an agent needs to interpret results. The remaining gap is control-parameter behavior (limit/include_seen), which is the one thing an agent could get wrong when calling 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 description coverage is 0%, so the description must compensate. It thoroughly explains the required 'query' semantics (every word must match, case-insensitive, substring matching), but says nothing about 'limit' or 'include_seen' — the latter is especially ambiguous since default true gives no clue whether seen messages are filtered in or out.

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 ('Search all messages') plus the exact fields searched (subject, sender, body, attachment text), so the agent knows this is a full-mailbox text search. It does not explicitly contrast with siblings like grep_item or list_threads, so differentiation is inferred rather than stated.

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?

'Use it to answer questions about earlier messages' gives a clear positive use case and implicitly scopes it to recall-style queries. There are no exclusions or named alternatives (e.g., when to prefer grep_item or get_thread_context instead), so it falls short of a 5.

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