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

With no annotations, the description carries the burden and does so well: it discloses that URL keys are masked, that only header names (not values) are returned, that deliveries are capped and include last success/failure, and that payload_format is also answered. It omits auth/permission requirements and any pagination or result-limit behavior for the webhook list itself.

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?

Front-loads the definition of the resource, then enumerates the returned fields in a single dense but scannable sentence. Parentheticals are used efficiently (masking, names-only headers, payload debugging) with no filler sentences.

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?

There is no output schema, so the description must describe returns, and it does so in detail including masked fields and the payload_format answer. Remaining gaps are moderate: no mention of the default/maximum delivery retention window beyond the schema's 50 cap, and no auth or result-size caveats.

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 baseline is 3, but the description adds real meaning: it explains that each webhook belongs to one number via `account`/`connection_id`, and clarifies that include_payloads returns the exact JSON body sent per delivery. The `deliveries` count parameter is only implied through the listing description.

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 (lists) and resource (webhooks), plus a definition of what a webhook is in this system (URLs Parley calls on message/reaction/deletion events). It clearly distinguishes the read operation from the write-oriented siblings create_webhook/update_webhook/delete_webhook, though it never names those siblings explicitly.

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 rather than stated: the include_payloads remark ('use it to debug a receiver') is the only explicit when-to-use cue, and there is one for payload inspection. No guidance on when to prefer this over list_connections-adjacent tools, no prerequisites, no exclusions.

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