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

Annotations already cover the safety profile (readOnlyHint=true, openWorldHint=false), and the description adds context annotations cannot carry: the tool requires an authenticated Awning session and will prompt the user to sign in if not. It also hints at returned content (status per booking, suggested next action), though it says nothing about ordering, volume, or pagination.

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, each doing distinct work: what the tool returns, the auth prerequisite, and the sibling routing. The most selection-critical information 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?

With no output schema, the description does describe the shape of results (per-booking status and next action) and the sign-in failure mode, which is what an agent needs to call it correctly. Some minor gaps remain around result volume/ordering and how the default 'upcoming' period behaves, but nothing blocking.

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% and the single 'period' enum is fully documented in the schema, so the baseline applies. The description never mentions the period filter, adding no syntax or default-behavior information beyond what the schema already states.

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?

Names a specific resource and scope ('the signed-in user's bookings across all businesses') plus what each item carries ('status and what to do next'). It also explicitly distinguishes itself from get_booking, so an agent can choose between them without reading either 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 a concrete use case ('answer "what have I booked?"') and names the alternative for the adjacent case ('for one booking by id use get_booking'). The routing condition is explicit, not inferred.

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