taskguard_add_checkpoint

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

No annotations exist, so the description must disclose behavior. It only mentions 'makes progress auditable,' which is a purpose statement. No information about side effects, idempotency, permissions, or error conditions is provided.

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 sentences, no fluff. Every word contributes to the core message. Ideal length for an agent to quickly grasp the tool's purpose.

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 no output schema and no annotations, the description is insufficient. It omits how sessionId relates to checkpoints, what happens if the session doesn't exist, and the semantics of optional fields (dueHint, description). The agent needs more detail 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 0%, yet the description provides no explanation of the two parameters (sessionId and checkpoints) or their sub-properties (label, dueHint, description). The context 'breaking a task into steps' loosely implies checkpoints are steps, but it's not explicit.

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 is for breaking tasks into measurable steps (checkpoints) to make progress auditable. The verb 'add_checkpoint' is specific and distinct from sibling tools like 'update_checkpoint' or 'add_evidence'.

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 says 'Call this when breaking a task into measurable implementation or research steps,' providing clear context for when to use it. Does not mention exclusions or alternatives, but the usage scenario is well-defined.

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