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

Annotations declare it is a non-read mutation with open-world reach; the description adds genuinely useful context beyond that: the job transitions to active on signing, the recipient default, a confirmation requirement, and the API-key prerequisite. The only blemish is the mild tension between "you can switch that off" and "confirm with the user before each call."

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?

The opening sentence is well front-loaded, but the description then duplicates itself verbatim ("Emails the saved proposal to the client for e-signature" and "The job turns active when the client signs" each repeat earlier content). The redundancy wastes a meaningful fraction of the text.

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 two-parameter send tool with no output schema, the description covers the side effect (job activation), recipient resolution, confirmation behavior, and auth requirement. It is nearly complete; only the missing return/error behavior and sibling routing keep it from a 5.

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% and both parameters are already documented, including the to_email default. The description restates the same default without adding format or constraint detail, so baseline 3 is correct.

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 ("Email the proposal") plus the goal (for e-signature), which separates it from siblings like knowify_save_proposal and knowify_send_invoice. An agent can identify the action and its purpose without opening the 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?

It gives context (recipient defaults to the client contact, human-confirmation expectation) but never states when to choose this over alternatives such as knowify_save_proposal or the invoice-sending tools. Usage is implied rather than explicitly contrasted with siblings.

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