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

Annotations already cover safety (readOnlyHint true, destructiveHint false, openWorldHint true), so the description only needs to add scope. It does: the result set is bounded to live attempts plus those from the last 30 days, and each entry carries status and a last-event timestamp — behavior an agent could not infer from annotations.

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 sentences, zero filler. The result scope is front-loaded and the sibling routing comes second, which is the right order for an agent deciding whether to call this tool.

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 parameters and no output schema, the description carries the burden of describing the return, and it does so at a high level (status plus last-activity time). It omits ordering, result caps/pagination, and what status values are possible, which leaves minor gaps for a 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?

The tool takes no parameters, so there is nothing for the description to disambiguate; the baseline for a zero-param tool applies. The description does at least make clear that no filtering argument is needed and that the 30-day window is fixed behavior rather than a caller-supplied option.

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 gives a specific verb and resource ("List the person's automatic applications") and immediately defines scope: live attempts with status and last-activity time, plus those submitted in the last 30 days. That is enough for an agent to distinguish it from auto_apply_get, auto_apply_cancel, or auto_apply_retry without opening any 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 explicitly routes the agent to auto_apply_get when it needs one attempt's questions and history, which is the closest competing tool. It stops short of addressing the other auto_apply_* siblings (cancel, retry, review, start), so the guidance is clear but not exhaustive.

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