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

Annotations already declare readOnly, idempotent, non-destructive and closed-world, so the safety profile is covered. The description adds genuinely new behavioral context: the ordering ('Newest-first'), the fact that a plan gate (BUSINESS+) is required, and that both successes and failures are returned.

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 compact sentences, front-loaded with purpose, then return shape, then ordering and plan gate. No filler, though the return-field list is dense and could be ordered slightly more logically.

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 usefully enumerates returned fields, plus ordering and the plan gate. The main uncovered area is pagination/cursor behavior, which matters for a newest-first list tool.

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 only 50% (cursor and webhookId are undocumented), so the description carries some burden. It adds no parameter meaning beyond 'Newest-first' loosely hinting at cursor ordering, and says nothing about limit, cursor semantics, or the success filter syntax.

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 recent delivery attempts for a webhook') and clarifies scope with '(success or failure)'. It is largely distinguishable from siblings like list_webhook_events and get_webhook, though it never names them, leaving a small risk of confusion with the events tool.

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 context is implied by 'recent delivery attempts' and the stated plan gate ('webhooks (BUSINESS+)'), but there is no explicit when-to-use vs when-not, nor a pointer to alternatives such as list_webhook_events or test_webhook. Adequate but with clear gaps.

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