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

Beyond the annotations, the description explains OAuth behavior for Google/Outlook (authorize_url + poll_token), direct credential updates for CalDAV/iCal, and the iCloud App-Specific Password constraint. These are important behavioral details an agent needs to invoke the tool correctly.

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 description is front-loaded with the core purpose, then organized by provider case. Each sentence contributes specific, actionable detail with no obvious filler.

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?

There is no output schema, but the description explains the key return shapes for OAuth and direct-update flows. Combined with the schema and annotations, it gives enough context to call the tool correctly across providers.

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%, so the schema already documents most parameter requirements. The description adds meaningful provider-specific semantics, especially that iCloud requires a newly generated App-Specific Password and that OAuth accounts should omit the password.

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 verb and resource, "Re-authorize a stale account," and ties it to provider-specific status/flow conditions. It clearly distinguishes reauthorization from the sibling connect_* tools by focusing on stale accounts and existing credentials.

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 clearly identifies when this tool applies, especially for Google/Outlook accounts with status needs_reauth, and gives provider-specific usage instructions. It does not explicitly compare against alternatives like connect_account or connect_caldav_account, so it stops short of a 5.

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