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

With no annotations, the description carries the load and does well: it discloses the default 45 s wait (configurable up to 50), and what happens if the user answers late — the reply returns as a message to this task or via phone_result. It omits failure/timeout behavior and any permission assumptions, keeping it short of a 5.

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?

Purpose and trigger are front-loaded, and every clause adds information (wait bounds, async fallback, routing). The heavy parenthetical nesting makes it slightly hard to parse but nothing is wasted.

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 5-param tool with no output schema and no annotations, the definition covers invocation, timing, and answer retrieval well enough to call correctly. Only edge cases like timeout-with-no-answer handling are unaddressed.

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?

At 40% schema coverage the description must compensate, and it does for the key params: wait_seconds default and 50 s ceiling, the role of from for routing answers back to the task, and options as up-to-four tap answers with a Yes/No default. Only 'why' is left to the schema's own note.

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 ('Ask the user a short question on their iPhone') plus the answer mechanism (up to 4 tappable options, default Yes/No). It explicitly distinguishes itself from the sibling phone_result by naming it as where a late answer can be retrieved.

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 a clear trigger: 'when you need their OK or a choice and they may be away from the Mac,' which tells the agent this is for remote user confirmation. It does not, however, contrast against neighbors like notify_user or ask_agent, leaving the agent to infer which channel to pick.

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