upload_multiple_files

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

With no annotations, the description carries full burden and provides rich behavioral details: automatic retry (3 attempts), parallel uploads (5 concurrent default), processing state monitoring (waits for ACTIVE state), performance estimates (2 files = ~30 seconds, etc.), and return values (URIs, error details for failures). It doesn't mention authentication or rate limits, but covers key operational traits.

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?

Well-structured with sections (TYPICAL USE, SCALES TO, FEATURES, WORKFLOW, PERFORMANCE) and front-loaded key information. Some redundancy exists (e.g., 'UPLOAD MULTIPLE FILES EFFICIENTLY' could be tighter), but most sentences earn their place by adding value.

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 tool with no annotations and no output schema, the description provides comprehensive context: purpose, usage scenarios, behavioral traits, performance estimates, and return values. It adequately compensates for the lack of structured fields, though it could mention error handling or prerequisites more explicitly.

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%, so the schema already documents all parameters. The description adds context about the workflow ('Provide array of file paths') and implies batch optimization, but doesn't add significant semantic details beyond what the schema provides. Baseline 3 is appropriate when schema does the heavy lifting.

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 uploads multiple files efficiently with smart parallel processing, distinguishing it from the sibling 'upload_file' tool for single files. It specifies the verb 'upload' and resource 'multiple files' with scope (2-40+ files).

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?

Explicit guidance is provided: use for 2-10 files for multi-document analysis, code reviews, or comparative tasks; scales to 40+ files for dataset processing; and explicitly states 'Use upload_file for single files instead,' clearly differentiating from the sibling tool.

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