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

Annotations already declare read-only, idempotent, non-destructive behavior, so the description's job is to add context — and it does: default sort order (newest first), the inlined contacts shape, and pagination defaults (limit 50, max 500, offset). It does not say whether a total count is returned, but against a full annotation set this is solid added context.

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?

A single dense sentence that front-loads the resource and ordering, then covers the inlined shape, filtering, and pagination with no wasted words.

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 four-parameter list tool with no output schema, the description covers ordering, result shape (inlined contact), filtering, and pagination adequately. Only minor gaps remain, such as whether a total count or next-page indicator accompanies results.

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 all four parameters including the ISO timestamp examples and defaults. The description largely restates those defaults and the ISO format, adding little beyond the schema, which matches the baseline 3 for a well-documented schema.

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 ('List bookings') plus meaningful qualifiers: sort order ('newest first') and the inlined invitee contact shape. The resource is distinct from siblings like list_contacts and list_events, though it never explicitly contrasts itself with them.

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?

Usage is implied through the filtering and pagination instructions, which tell an agent how to narrow and page results, but there is no explicit statement of when to reach for this tool versus alternates, nor any prerequisites or exclusions.

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