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

Goes well beyond the readOnlyHint annotation: delayed quote marking at read time, never cached, empty-portfolio returns {has_portfolio: false, how_to_start} rather than an error, auth failure semantics (AUTH_REQUIRED), and a per-response _meta.disclaimer. These are exactly the operational traits an agent could not infer from annotations alone.

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-loaded with the core purpose and response shape, then layered constraints; every sentence carries new information. It is dense with parentheticals and semicolons, which slightly reduces readability, but there is no filler.

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 output schema, the description compensates by enumerating the returned fields (portfolio, positions, totals, position_theses, summary, has_portfolio, optional recent_trades) plus the empty-state and disclaimer behavior. An agent has everything needed to call and interpret it.

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 description coverage is 100%, and the description largely restates the same facts (history_limit 1..50 default 20; include_history adds recent_trades). It adds marginally by tying recent_trades to the include_history flag, but the schema already carries the numeric bounds and defaults, so baseline 3 applies.

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 precise resource and scope: the caller's own paper/practice portfolio on Oxford Ledge, matching the /practice/ web sandbox snapshot. It names the exact response shape and clearly separates this from the real-portfolio sibling get_portfolio_positions by emphasizing 'paper' and 'YOUR ... only'.

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 clear conditions: authenticated Oxford Ledge caller (API key or linked OAuth), caller's own portfolio only, local stdio server gets AUTH_REQUIRED, and include_history opts into fills. However, it never names an alternative tool (e.g. ol_paper_trade or get_portfolio_positions) or an explicit when-not-to-use condition, so routing guidance is strong but not complete.

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