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

Goes well beyond the annotations (write, non-destructive, open-world) by disclosing the permission-failure condition, the workflow side effect a milestone change can set off, the external impact ('reaches other people'), the confirmation requirement, and that it returns the previous milestone and new date. This is exactly the extra context an agent needs before issuing a mutation.

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 first two sentences restate the same action almost verbatim ('Move a job to another milestone, as you would in the job file' vs 'Moves one job to another milestone the way you do in the job file'), which is wasted space. The confirmation guidance is also split across two sentences that can read as conflicting ('you can switch that off' vs 'confirm with the user before each call').

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 reports the return payload (previous milestone and new date), and it covers permission failure, side effects and confirmation. It is complete for a 2-param mutation, with no significant behavior left undisclosed.

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%, with job_id sourced from list_jobs and an explicit milestone enum, so the schema carries parameter meaning. The description adds no format or naming detail beyond what the schema already provides, making the baseline 3 appropriate.

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 ('Move a job') and resource ('to another milestone'), and pins the mental model to the job-file action the user already knows. It is readily distinguishable from the read/write job siblings (get_job, create_job) since none of them touch milestone state.

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?

Gives concrete usage context: it fails if the role does not permit the move, it may trigger a workflow, and each call should be confirmed with the user by default. It does not name explicit alternatives, but no sibling competes for this operation, so the missing exclusion is minor.

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