upload_course_file

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

Annotations include destructiveHint: true, which the description does not contradict. The description adds that the file ID can be used downstream, but does not disclose potential side effects like overwriting existing files (on_duplicate parameter) or permission requirements. With annotations already flagging destructiveness, the description adds minimal extra behavioral context, so a 3 is appropriate.

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 two sentences, front-loaded with the main purpose, and includes a useful downstream usage note. No wasted words, and it is well-structured for quick parsing.

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 5 parameters, 100% schema coverage, and no output schema, the description is fairly complete. It explains the purpose, the return value usage, and the main parameters are covered by the schema. It could mention the on_duplicate behavior or folder_path default, but those are in the schema. The description is sufficient for an agent to use the tool correctly.

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 all parameters are documented in the schema. The description adds a note about the returned file ID usage, but does not add extra meaning to parameters beyond what the schema provides. Baseline 3 is correct since the 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 a local file to Canvas course storage, with a specific verb ('Upload') and resource ('file to Canvas course storage'). It distinguishes from siblings like download_course_file and read_course_file by focusing on the upload action, and mentions the returned file ID can be used with add_module_item or send_conversation, which adds context.

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 when to use this tool (when you need to upload a file to a course) and provides downstream usage examples (add_module_item, send_conversation). However, it does not explicitly state when not to use it or mention alternatives like upload to a different location, but the context is clear enough for an agent to decide.

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