annotate_wisdom

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

With no annotations provided, the description carries the burden of behavioral disclosure. It explains the append/non-destructive timestamped behavior and the search-to-place mechanism, which is useful context. However, it doesn't specify whether the file is modified in-place destructively, whether existing content is preserved, or any side effects on the wisdom file structure—gaps that matter given zero annotation coverage.

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?

The description is compact—three sentences that efficiently convey purpose, usage trigger, and mechanism. The analogy ('sticky note for future sessions') is evocative and aids comprehension. No wasted words.

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 tool creating a sidecar file modification with no output schema and no annotations, the description covers the core behavior adequately. It explains placement logic (search vs append-to-end), the timestamping behavior, and the use case. However, it doesn't clarify the relationship between 'section' and 'file_path' parameters (which target different file types) or what happens on no-match, which are meaningful gaps for correct invocation.

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 all four parameters have descriptions. The description adds the search-to-placement behavior (that 'search' locates where to place the annotation) and explains 'comment' is the sticky-note text. This adds behavioral context beyond the schema but doesn't significantly enrich parameter semantics beyond what schema already documents.

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 clearly states the verb (annotate/add) and resource (existing wisdom), and explains it's for corrections, clarifications, or new context. It distinguishes from siblings like save_wisdom (which presumably adds new wisdom entries) by focusing on augmenting existing entries, though it doesn't explicitly name the sibling alternative.

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 provides explicit when-to-use guidance ('when you discover a previous assumption was wrong, needs clarification, or has new context') and explains the mechanism (timestamped, appended below matching entry, like a sticky note). However, it doesn't explicitly state when NOT to use it versus save_wisdom for brand-new knowledge, which is an implied but not explicit distinction.

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