check_session

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

With no annotations, the description carries the full burden. 'Report whether' reasonably implies a read-only, side-effect-free query, which is useful context. However, it does not disclose the return shape (boolean vs. status text) or whether the check can refresh/alter the session, leaving real behavioral questions open.

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?

A single front-loaded sentence with zero filler; the subject and condition are stated immediately.

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 trivial no-arg check this is nearly sufficient, but with no output schema the description should state what 'report' actually returns (e.g., a boolean or status string) so the agent knows how to interpret the result.

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 zero parameters, so the baseline is 4. There is nothing for the description to disambiguate, and the schema coverage is 100%.

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 ('Report') and resource ('current WebVPN session is authenticated'), making the purpose immediately clear. It is naturally distinct from the sibling download_* tools, though it never explicitly contrasts itself with them.

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?

There is no explicit when-to-use or when-not-to-use guidance. The usage is only implied – an agent would infer it should be called before attempting downloads that need an authenticated session, but the description never says so.

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