list_checkpoints

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

Without annotations, the description carries full burden; it conveys the operation is a read-only list with ordering, but does not mention error behavior (e.g., missing file) or limitations.

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?

Single sentence, no unnecessary words, front-loaded with the action and resource.

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 simple list tool with one parameter and no output schema, the description is nearly complete; only lacking a brief mention of what a checkpoint is or how to interpret results.

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% and already describes the parameter; the description adds nothing beyond the schema, so baseline of 3 is appropriate.

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 clearly states the verb 'list', the resource 'checkpoint backups for a .tldr file', and the ordering 'newest first', distinguishing it from sibling tools like 'save_checkpoint' and 'restore_checkpoint'.

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 description implies usage for viewing backup history but does not explicitly state when to use this tool versus alternatives (e.g., when you need to restore a checkpoint) or when not to use it.

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