upload_file

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

With no annotations, the description carries the full burden of disclosing behavioral traits. It only mentions setting mimeType for 'proper handling' and does not address important behaviors like overwrite policy, permissions, size limits, or return values. 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?

The description is exceptionally concise, with exactly two sentences that front-load the core purpose and then provide targeted guidance. Every sentence adds value, with no redundancy or filler.

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?

Given the tool has 6 parameters, no annotations, and no output schema, the description is incomplete. It omits guidance on parentFolderId, teamId, return behavior, failure modes, and other critical context, making it insufficient for a tool with this complexity.

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 67%, so the description adds meaningful semantics beyond the schema. It clarifies content encoding (base64 for binaries, text otherwise) and emphasizes mimeType's role, which compensates for missing parameter descriptions for those fields.

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 'Upload a new file' with a specific verb and resource. It distinguishes from siblings like update_file and delete_file by emphasizing 'new', making the purpose unambiguous.

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 implies usage for creating new files but does not explicitly state when to use this tool over alternatives or provide exclusions. It offers contextual guidance on content encoding but lacks clear 'when-not-to-use' information.

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