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

The description goes beyond the annotations by clarifying that a single call can perform several distinct repositioning behaviors (filing, nesting, attaching, ordering). It does not detail side effects like auth requirements or return value, but the annotations already signal that this is a non-read-only, non-destructive, non-idempotent mutation, and the description adds useful operational context.

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 a single, front-loaded sentence that lists the key operations first and then uses a concise analogy to reinforce the behavior. There is no filler or repetition of schema information.

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 mutation tool with six parameters, a complete schema, and useful annotations, the description supplies enough conceptual context for an agent to select and invoke it correctly. It does not describe return values, but no output schema exists and the operation's purpose is clear from the description and parameter documentation.

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 already has a description, so the baseline is 3. The description adds value by mapping the conceptual operations—file under collection, nest under parent, attach to project, order against siblings—to the corresponding parameters, giving an agent a higher-level understanding of how the parameters relate.

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 names a specific action ('file', 'nest', 'attach', 'order') on a specific resource (a document), and clearly differentiates this from sibling tools like move_issue or reorder_milestones by scoping it to document positioning. The sidebar-dragging analogy reinforces the intended operation without ambiguity.

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 provides a clear context: use this when you would drag a document in the sidebar to reposition it, file it, nest it, or attach it. It does not explicitly mention alternatives such as move_issue, but the doc-specific scope and the sidebar analogy make the intended usage evident.

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