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

With no annotations, the description carries the load and discloses genuinely non-obvious behavior: ordering is oldest-to-newest, there is a cap on retained checkpoints, and — importantly — the list is a history rather than a stack, so checkpoints on abandoned paths remain listed and restorable. It does not state permission/auth needs or the return format, but the disclosed semantics are unusually rich.

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-loads the core purpose and the return contents in the first sentence, then uses the second paragraph only for the non-obvious history-vs-stack caveat. Slightly long for a zero-param lister, but nearly every sentence adds real information.

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 annotations, no output schema and no parameters, the description fully compensates by describing the returned fields, the ordering, the retention cap and the restore-path behavior. An agent has everything it needs to call and interpret this tool 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?

The tool takes zero parameters, so the baseline is 4. The description correctly implies no filtering or input is required for this listing.

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?

Specific verb (List) plus resource (checkpoints) plus scope (of this computer) plus the exact contents returned (when taken, size, which one is running, marked 'YOU ARE HERE'). It is immediately distinguishable from its create_checkpoint, delete_checkpoint and restore_checkpoint siblings.

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 two concrete triggers — check before a risky change, and check before saving another because the number kept is limited — which is clear situational context. It stops short of explicitly naming the sibling to use for the save/restore actions, so it is clear but not fully routed.

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