authenticate

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

With no annotations to rely on, the description carries the full burden and does so admirably. It discloses that secrets are stored in macOS Keychain, never enter the assistant context via MCP elicitation, sessions auto-refresh, and force re-collects/overwrites existing secrets. These are meaningful behavioral traits beyond the bare action of 'authenticate'.

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 four compact sentences, each adding distinct value: core purpose, inference behavior, secret-handling guarantee, and force semantics. It is front-loaded and free of fluff.

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 two-parameter tool with no output schema and no annotations, the description covers all essential call-time knowledge: what secrets are, where they are stored, how inference works, context safety, auto-refresh, and when to use force. An agent has enough to select and invoke 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 coverage is 100%, so the schema already documents both parameters. The description adds a concrete example for force ('rotated or expired keys') but mostly repeats the schema's own description, so it does not significantly extend parameter understanding.

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 states a specific action ('Authenticate a server') and adds concrete resource details: collecting and storing required secrets in macOS Keychain, with a distinct mechanism (MCP elicitation) and a force flag for re-collection. This clearly differentiates it from siblings like auth_status, search, and call_tool, which serve different purposes.

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 gives clear operational context: when to use force=true, how it handles missing auth schemas, and the fact that sessions refresh automatically. It does not explicitly name alternatives or state when not to use this tool, but the intended context is evident and actionable.

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