checklist_apply

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

Annotations only declare the generic write/safe/local profile (readOnlyHint=false, destructiveHint=false, openWorldHint=false). The description goes well beyond them: it discloses the 10-upgrades-per-call confirmation batching, the auto-save behavior for keep/lower lines, and names the exact return fields (counts, pending_evidence, skills_without_achievements, key_skills_without_achievements).

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 core operation and its re-invocation rule are front-loaded in the first sentence, and the rest is dense but mostly load-bearing (return fields, follow-up ordering). It is longer than typical and blends downstream agent instructions with tool semantics, which costs a point, but little is redundant.

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 stateful, form-driven write tool with no output schema, the description covers when to call it, what it persists automatically vs. confirms, what the response contains, and what the agent should do next (achievements first, then key skills, gap_report fallback). Nothing an agent needs to invoke it correctly is missing.

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%, so both `path` and `profile` are already documented in the schema, including the default-profile fallback. The description adds no syntax or format detail for the parameters themselves, so 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?

Opens with a specific verb+resource: 'Save the skills the person marked in a checklist file.' It explicitly anchors itself to the sibling workflow ('after checklist_new', 'save with set_skills'), so an agent can distinguish it from checklist_new, set_skills, and add_bullet without opening any schema.

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 explicit triggering conditions ('after checklist_new, once the person says they are done, and again to resume') and an explicit re-invocation rule ('call again while upgrades_not_asked_yet is not empty'). It also states what NOT to do ('Ask about nothing else', 'Never write an achievement for them'), which is unusually complete routing guidance.

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