checkpoint_session

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

No annotations, so description carries burden. It mentions storing decisions, open loops, next actions etc., and that it's 'compact' and does not pollute durable memory. However, it does not explain overwriting vs merging behavior or 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?

Two sentences: first defines purpose, second gives usage guidance. No wasted words, front-loaded 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?

Description covers core use case but lacks details on return value, persistence behavior, and handling of multiple checkpoints per session. With 10 parameters and no output schema, more context would be beneficial.

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% with descriptive parameter descriptions. The tool description adds little beyond the schema, only reinforcing the 'compact' nature. Baseline 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?

Description states 'Store a compact checkpoint of the current work state' with clear verb and resource. It also provides usage context differentiating from siblings (e.g., not polluting durable memory).

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 says 'Use this when a task spans windows or terminals and you need the next session to recover decisions, open loops, and next actions without polluting durable memory.' Clearly indicates when to use and implies alternatives for durable memory.

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