check_tls_endpoint

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

With no annotations provided, the description carries the full burden, and it discloses meaningfully: it reads the certificate the host 'actually serves' (live data, not config), accepts any port, and refuses private/reserved address resolutions — an important SSRF-style safety behavior. The enumerated findings also tell the agent what classes of issues it will surface. It omits failure behavior (timeouts, unreachable hosts, non-TLS ports), but the disclosed traits go well beyond the bare schema.

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 dense sentences with zero filler: the first front-loads the action and finding set, the second adds the safety constraint. Every phrase earns its place, including the parenthetical finding list that would otherwise require a schema or docs lookup.

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 network-dependent tool with an output schema, the core purpose, constraints, and safety behavior are well covered, and return values are handled by the schema. The gaps are the unexplained role parameter and the absence of failure-mode context (timeouts, connection refusal, non-TLS endpoints), which an agent would need to anticipate errors when invoking a live-network 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?

Schema description coverage is 0%, so the description is the only source of parameter meaning, and it does clarify host ('public host:port') and port ('Any port'). However, the role parameter is completely unexplained — its likely semantic (e.g., SNI name) is left to the agent to guess, which is a real gap given nothing else documents it.

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 action sequence (connect to a public host:port, read the served certificate) and enumerates the exact findings (expiry, weak key, weak signature, self-signed, hostname not in SANs, CA expiry). It also distinguishes itself from the sibling find_certs_in_config by framing this as the live-endpoint variant, so an agent can tell them apart 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?

The phrase 'run the same findings as find_certs_in_config on it' clearly situates this tool against its sibling, implying the config-checking alternative for offline analysis. The 'Refuses hosts that resolve to private or reserved addresses' constraint and 'Any port' scope give an agent concrete boundary conditions for when the tool applies. It stops short of an explicit when-not rule, but the routing signal is strong.

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