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

Beyond the annotations, the description discloses the approval workflow, the requirement for a matching authorizationId, current membership, token scope and a fresh passkey session, and that destructive/external/privileged actions retain domain safeguards. This adds substantial operational context that annotations alone do not convey.

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 front-loaded and has no wasted framing, but the second sentence is dense and packs multiple authorization constraints into one long clause. It remains readable and appropriately sized for a complex tool.

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 destructive, open-world command execution tool with eight parameters and no output schema, the description covers the critical usage path, approval requirement and prerequisite checks well. It does not describe the execution result or failure behavior, which leaves a minor completeness gap.

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 already high at 88%, but the description adds useful cross-tool semantics: fields, target and reason must match those used by prepare_command, and authorizationId is omitted only for direct commands. It does not add much about commandId, org, app, environment or files beyond the schema, so it is not a full 5.

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 states a specific verb and resource ("Execute a command") and immediately distinguishes routine direct execution from approval-gated execution. It names sibling tools get_command_schema and prepare_command, so an agent can tell how this tool fits with them without opening other definitions.

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 clearly says a routine command marked execution: direct runs immediately without authorizationId, while any other command requires approval and an authorizationId from prepare_command. The routing is strong, though it does not explicitly spell out the full call sequence or state what to do if prepare_command has not been called.

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