upload_attachment

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

No annotations are supplied, so the description carries the full behavioral burden. It does disclose the return payload and the non-obvious two-step semantics (upload then attach), which is genuinely useful. However it says nothing about permissions, file size limits, failure modes, or whether the token expires, all of which matter for a write-oriented upload endpoint.

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?

Two tight sentences with zero filler. The purpose is front-loaded and the downstream handoff follows immediately, so the most actionable information appears first.

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?

With no output schema, the description correctly compensates by spelling out the returned shape and how to consume it, which is the main ambiguity an agent faces. It is nearly complete for a 2-parameter tool, falling short only on error/limit behavior.

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% and both parameters are documented in the schema itself (absolute path, MIME type). The description adds no syntax, format, or constraint detail beyond that, so the baseline 3 applies.

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?

States a specific verb (upload) and resource (a file to Basecamp 2), and goes further by naming the concrete artifact produced (an attachment token). It also differentiates itself from siblings by naming create_todo and create_comment as the consumers of its output, so an agent can place it in the workflow without opening other schemas.

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 tells the agent that uploading alone does not attach anything and that both returned fields must be passed as an 'attachments' entry to create_todo or create_comment. That is an unambiguous when-to-use and how-to-chain instruction, which is exactly the guidance missing from most mutation tools.

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