clickup_attach_task_file

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

With no annotations, the description carries the full burden. It discloses a real constraint (base64 payloads should stay under ~200KB) and implies auth via auth_header, but says nothing about required ClickUp permissions, whether an existing attachment is duplicated or replaced, or what the call returns. Adequate, but gaps remain for a mutation tool.

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?

Three short sentences, front-loaded with the action and the required parameter, then the modes, then the escape hatch to the sibling tool. No 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?

For a 6-parameter attachment tool with a fully described schema, the description covers input modes, the one constraint that matters (payload size), and the alternative route for local files. It stops short of describing the resulting attachment record or behavior on repeat uploads, which is the main remaining hole given no output schema.

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%, so the baseline is 3; the description earns an extra point by stating combination semantics the schema does not express — that file_data needs file_name and that file_url is the mutually exclusive alternate path — and adds a size bound the schema lacks. It does not explain auth_header or workspace_id beyond the schema text.

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?

Specific verb+resource ("Attach file to task") with the required key stated immediately. It also enumerates the two supported input modes (base64+filename, URL), so the agent knows precisely which shapes of call are valid.

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 when-to-use rules per source type (base64 for files under ~200KB, URL for http/https) plus an explicit when-not that routes local files to the sibling tool request_attachment_upload. Both the alternative and the selecting condition are named.

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