upload-file-content

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

The description explicitly states that the tool overwrites existing files without warning, which is critical behavioral information. It also mentions size limits and decoding behavior. Annotations provide readOnlyHint=false, but the description's overwriting warning adds transparency.

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 relatively short but lacks clear structure. It starts with a vague statement, then provides tips in a list-like format. It could be more organized with a clear purpose statement followed by key points.

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 no output schema, the description does not explain return values. It covers size limits, overwriting, and path format for new files, but misses prerequisites (e.g., file existence) and authentication context. More detail on expected outcomes would improve completeness.

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?

The schema covers 100% of parameters with descriptions. The description adds value by explaining the body parameter's base64 encoding and server decoding, and describes the path format for new files, which provides context beyond the 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 tool name 'upload-file-content' clearly indicates its function. The description adds detail about base64 encoding and overwriting behavior, but the opening phrase 'The content stream, if the item represents a file' is vague and could be more direct.

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 a clear alternative (create-upload-session for files over 4MB) and warns about overwriting without warning. However, it lacks broader context on when to use this tool versus other sibling tools like copy-drive-item or get-drive-item.

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