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

Annotations already cover the safety profile (readOnly, idempotent, non-destructive), so the bar is lower; the description still adds real context by disclosing the sign-in prerequisite, that the flow is free/one email, and what the response contains. It stops short of describing response shape in detail, but no output schema exists and the orientation contents are enumerated.

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?

Three dense sentences, front-loaded with the blocking sign-in requirement before the orientation purpose, so the agent reads the prerequisite first. Every sentence earns its place, though the second sentence packs several output categories into one clause.

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 carries the burden of explaining return content and does so (cross-service jobs listed first, enabled services, available services, next steps). The auth prerequisite and call ordering are both covered, leaving nothing an agent needs in order to invoke it correctly.

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 100% and the single session parameter is fully documented in the schema, so the schema does the heavy lifting. The description references the sign-in flow the session relates to but adds no syntax or format detail beyond what the schema provides — baseline 3.

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 purpose — orientation for a new connection that surfaces cross-service jobs, enabled/available services, and next steps — plus the entry-point role via 'Call this first.' An agent can tell this apart from datailo_account or datailo_tools because it is explicitly framed as the starting orientation call.

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 gives explicit when-to-use guidance ('Call this first') and states the prerequisite sign-in path, naming the exact sibling calls (datailo_connect, datailo_connect_verify) plus the exception for OAuth/key connections. Nothing about when to invoke it is left to inference.

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