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

Annotations provide readOnlyHint=false and destructiveHint=false; description adds that it repeats without adding orders, stops at max_bars as a safety cap, and supports require_flat. No contradiction, and it supplements annotations with bounded-loop behavior.

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, no fluff, directly state purpose and key constraints. Front-loaded with the main action followed by supporting details.

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?

Given no output schema, the description explains termination conditions (complete, liquidate, max_bars) and optional guard. Could hint at return value but is fairly complete for a simple helper tool.

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 covers all 3 parameters with descriptions (100% coverage). The tool description only mentions max_bars and require_flat briefly, adding minimal extra meaning beyond schema. Base score 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 uses a specific verb ('advance') and resource ('authenticated run') with clear termination conditions (completes, liquidates, max_bars). It distinguishes from siblings like step_run and advance_until_next_session by framing as a repeatedly advancing helper for terminal waiting.

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 states this is a 'bounded helper' for 'terminal waiting' and mentions 'require_flat can enforce cash-only execution', indicating when to use and a specific guard. It doesn't explicitly exclude alternatives, but context is clear.

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