Retry a failed upload

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

Annotations already declare readOnlyHint=false and destructiveHint=false, so the description need not repeat that. However, it adds no additional behavioral context: it does not explain what happens on retry (e.g., whether a new job is created, if the original is replaced), whether authentication is required, or any side effects. The openWorldHint=true annotation suggests external effects, but the description is silent on that. For a mutation tool, this is a significant gap.

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?

Two sentences, both purposeful. The purpose is front-loaded and the identifier guidance is immediately actionable. No wasted words or redundancy with the schema.

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?

An output schema is present, so return values are covered. The description covers the core purpose and parameter selection, but it omits the requirement that one of the two identifiers must be provided (both are optional in the schema). It also doesn't state what constitutes a 'failed upload' or any error conditions. For a tool with two optional parameters and no required fields, this ambiguity is a notable 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 description coverage is 100% for both parameters. The description adds meaning by mapping requestId to async uploads and jobId to scheduled/queued uploads, which is not in the schema descriptions. This helps the agent select the correct parameter. It could further clarify that exactly one is required, but the mapping itself is valuable.

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 clearly states the tool's purpose: retrying a failed upload. It specifies the two identifier types (requestId for async, jobId for scheduled/queued) and the resource (failed upload). It does not explicitly name sibling tools or differentiate itself, but the purpose is unambiguous and actionable.

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?

The description provides guidance on which identifier to use based on upload type (requestId for async, jobId for scheduled/queued). However, it does not specify when to use this tool versus alternatives (e.g., cancel_scheduled, get_job_status, or upload tools), nor does it mention prerequisites like the upload being in a failed state. The guidance is clear on how to select parameters but not on broader usage context.

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