mac_ssh_run

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

No annotations are provided, so the description carries full burden. It states it runs arbitrary commands but does not disclose that this can have destructive side effects, does not describe what is returned (though output schema exists), and does not mention authentication behavior beyond optional key_path. The timeout behavior is noted, but overall the safety and outcome profile is underspecified for a remote execution tool.

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 well-organized: a one-line purpose, a short usage context, and a compact args list. It is front-loaded with the core purpose and avoids redundancy. The 'Quote internal spaces yourself' tip is a valuable, non-obvious addition that earns its place.

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 generic remote command runner, it covers the essential aspects: purpose, usage, and parameter details. It does not mention checking connectivity with mac_ssh_check or other prerequisites, but the output schema likely covers return values. Given its role as a low-level building block, it is reasonably complete, though it could benefit from a warning about potential side effects.

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 explain each parameter. It does so concisely: host (hostname or IP), user (account), command (single line, quote internal spaces yourself), key_path (optional explicit key), timeout (seconds before killed). This adds practical meaning beyond the raw schema.

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 opens with a precise verb and resource: 'Run an arbitrary command on the remote Mac via SSH.' It explicitly positions itself as the generic building block and contrasts with sim_* wrappers, making its unique role clear and distinguishing it from siblings.

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?

It gives direct routing guidance: 'Most callers should prefer the sim_* tools that wrap simctl directly; use this when you need something specific that doesn't have a wrapper.' This explicitly tells when to use it and when not, naming the alternative category.

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