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

With no annotations, the description carries the full behavioral burden and does so richly: entire filesystem and installed packages are replaced, uncommitted work is lost, the machine restarts and is briefly unavailable, running processes die, and a sleeping machine defers the restore until wake. These are non-obvious operational traits an agent must know before invoking.

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 single most important fact in caps ('THIS DISCARDS WORK'), then proceeds through mitigation, non-destructive nuance, and restart side effects. Every sentence carries unique information; nothing is padding.

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 destructive, restart-triggering operation with no annotations and no output schema, the description covers consequences, mitigation, reversibility of the checkpoint list, and availability impact — everything an agent needs to call it correctly and warn the user.

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 baseline is 3, but the description adds real meaning: it explains the motivation and semantics of keep_current_as ('save the current state as its own checkpoint first'), not just its name. The checkpoint parameter is left to the schema's pointer to list_checkpoints.

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 a specific verb and resource ('Put this computer back to a saved checkpoint') and immediately names the sibling it is not: create_checkpoint, delete_checkpoint, and list_checkpoints are all implicitly contrasted by the restore semantics. An agent can distinguish it from every other checkpoint tool without opening a schema.

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?

Explicitly frames the decision: this DISCARDS WORK, and 'Pass keep_current_as ... which is almost always what you want when you are not certain.' It also clarifies that later checkpoints survive and future saves branch, so the agent knows returning is cheap. This is exactly the when/when-not guidance the dimension asks for.

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