upload-file-content

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

Annotations already include destructiveHint=true. The description adds context about overwriting without warning and the 4MB size limit. No contradictions, and the additional details help the agent understand the tool's impact beyond the annotations.

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 concise, using a tip format to highlight key points. However, the first sentence is slightly awkward and could be more direct. Overall, it is efficient with no wasted verbiage, but structure could be improved slightly.

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?

The description lacks information about the return value or output of the tool, which is absent from both description and output schema. For a file upload tool, the response format (e.g., file metadata) is important for agent decisions. Additionally, prerequisites like authentication are not mentioned, though annotations partially cover safety.

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 100% and each parameter is well-described in the schema. The description adds global context (base64, size limit) but does not provide per-parameter insights beyond what the schema already offers. Thus, minimal added value for parameter understanding.

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 the tool is for uploading file content, with the first sentence 'The content stream, if the item represents a file' indicating the resource. It clarifies overwriting behavior and distinguishes from the sibling 'create-upload-session' for large files. However, the first sentence is somewhat vague and could be more explicit about the action.

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?

Explicitly advises using 'create-upload-session' for files above 4MB, provides the path format for new files, and warns that the tool overwrites existing files without warning. This gives clear when-to-use and when-not-to-use guidance relative to siblings.

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