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

With no annotations, the description carries the full burden and does disclose key side effects: deletion sends agents to "No section" rather than destroying them, moving to a non-existent section name creates it, and changes propagate to Mac and phone immediately. It omits permission requirements, reversibility/undo of delete_section, and idempotency of repeated moves.

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?

Purpose is front-loaded in the first clause, followed by a compact semicolon-delimited action table and a closing usage rule; almost no filler. The paragraph is dense and the action list could be broken into lines, but every clause carries 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 six-action, five-parameter tool with no annotations and no output schema, the description covers all six actions, their required inputs, and their main side effects, plus what list_sections returns. Remaining gaps are error behavior and the exact shape of returned section/agent objects beyond the brief list_sections note.

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 0%, so the description must compensate and largely does: it maps each parameter to its action (section = the group name, name = new name, agents = names or ids, section = where to, "none" for No section). The distinction between the singular `agent` and the plural `agents` parameters is never explained, and `name`/`section` are overloaded across actions, leaving some ambiguity.

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 and resource ("Organise the user's agents on Caddie's Agents page: sections ... and names") and immediately enumerates the six supported operations, so the agent knows exactly what domain it operates on. It does not, however, distinguish the embedded rename_agent action from the sibling update_agent, nor list_sections from list_agents, which leaves real ambiguity against the sibling set.

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 instructs "Use this instead of telling the user to drag agents around," which is a concrete when-to-use rule, and the per-action breakdown tells the agent which action to pick for which intent. It stops short of stating when NOT to use it, e.g. when update_agent or archive_agent is the right sibling.

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