start_session

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 hard gating behavior (commands are inert until this runs) and the challenge-response PIN flow, including the agent's required action. It omits session lifetime, idempotency of repeated calls, and failure behavior when no server is connected.

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?

Three short sentences with no filler: purpose first, then the prerequisite constraint, then the conditional retry procedure. Every sentence earns its place and the most important constraint is front-loaded.

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 one-parameter, no-output-schema, no-annotation tool, the description covers purpose, ordering semantics, and the conditional PIN path. Remaining gaps (session lifetime, error behavior when disconnected, whether repeated calls are safe) are minor but real.

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% for the single 'pin' parameter, so the description must compensate, and it does: it explains that pin is conditionally required, only after the server reports a PIN challenge, and that its value must be obtained from the user. It does not describe the expected format or length of the pin.

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 (start) and resource (a tool-use session on the connected ServerKit server), and implies a prerequisite relationship to connect via 'connected'. It is clear what the tool does, though it does not explicitly contrast itself with the sibling 'connect' or 'end_session' beyond the ordering hint.

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 states the sequencing rule: it 'must be called once before run_command/run_command_sudo will do anything', which names both the alternatives and the condition that selects this tool. It also specifies the PIN follow-up path, telling the agent to ask the user and re-call with the pin argument.

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