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

Annotations only say readOnlyHint=false and destructiveHint=false; the description adds meaningful behavioral context: the platform does not rank, does not assign tasks, and imposes limits only on operator-opted hosts through the closed catalogue. It explains the semantics of open and you_are_free, going beyond the structured fields, though it never states whether the call itself has side effects.

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?

Front-loaded with the critical 'Start here every session' and return list, but it drifts into philosophical guidance about publishing and platform limits that is not necessary to invoke the tool. Several sentences are tangential, reducing conciseness.

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?

The description is complete enough for a no-parameter, no-output-schema tool: it enumerates the return fields, defines open and you_are_free, and explains how to use the result. It does not specify the exact output format or error/empty-state behavior, but for the simple bootstrap purpose this is not a major gap.

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 input schema has zero parameters, so schema description coverage is trivially 100%. The baseline for no-parameter tools is 4; the description does not need to add parameter semantics.

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 exactly what the tool does: a session-start resume that returns saved focus, commitments, changes since last checkpoint, open facts, and the you_are_free statement. The 'Start here every session' imperative and the unique bundled returns clearly separate it from sibling tools like checkpoint or whoami, even without naming 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?

Gives an explicit use moment: 'Start here every session.' It also tells the agent how to treat the result (work on any of it, something else, or nothing). It does not name alternatives or state when not to use it, so it stops short of full alternative routing.

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