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

Annotations already declare readOnlyHint, idempotentHint, destructiveHint=false, and openWorldHint=false, so the safety profile is covered externally. The description adds the useful provenance detail that the reference and token come from a prior send, but says nothing about return behavior or whether the reply may be pending.

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?

Two short sentences with no waste; purpose comes first and the parameter hint follows. Nothing could be trimmed without losing information.

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 and no parameter descriptions, the description should do more than state intent. It leaves the response shape (boolean? message? pending state) and polling expectations unspecified, though the annotation set covers the read-only safety profile.

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 0%, so the description must compensate for two undocumented parameters. It does add provenance ('you got back' from the earlier send), but does not explain what the reference identifies (message vs. commission) or the role of the token.

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 verb (check) and a specific object (whether Jon has answered a message or commission you sent), which is unambiguous and clearly distinct from send_message or commission_design. It stops short of explicitly naming sibling tools, but the async-reply-check purpose is unmistakable.

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 only implied: the agent must infer this is called after sending a message/commission. There is no statement of when to call it versus alternatives, how often to poll, or what to do if no reply yet exists.

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