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

With no annotations, the description carries the full burden and does well: it discloses the storage cost against the project owner's quota, the one-time nature of the upload link, the 100 KB cap for direct content, and that a direct attach notifies no one. It omits permission/auth requirements and whether attachments can be replaced or how failures surface.

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?

Every sentence earns its place: scope, when-to-use, cost, mode selection, notification behavior. The mode-selection sentence is long but front-loads the primary path and the size/type criterion that actually decides the branch.

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 does explain what mode 2 returns (upload link + curl command) and what mode 1 does (direct attach, no notification). It stops short of describing what a successful direct attach returns, so an agent cannot chain to get_attachment from the description alone.

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 already 100%, so the baseline is 3, but the description adds real semantics beyond it: the 100 KB ceiling, the 'omit content' branch producing an upload link plus curl command to run in a shell with the real file path, and which file types each mode suits.

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 (attach) plus the resource and the exact target entity types (epic, task, question) with their key formats. An agent can distinguish this from list_attachments/get_attachment purely from the verb, no schema inspection needed.

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?

Gives an explicit when-to-use constraint ('only when the user asks for it or it is a deliverable'), a decision rule between the two invocation modes based on file type and size, and names a sibling (add_comment) for the notification follow-up. This is about as complete as usage guidance gets.

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