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

Annotations already declare readOnly/idempotent/non-destructive, so the safety burden is covered. The description goes further by disclosing result ordering (newest first), that full text is returned, that images surface under an `images` key with a pointer to contextli_get_note, and that label filtering is ANY-match and case-insensitive. Missing only rate-limit/authorization context.

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 core behavior in the first sentence and lays out filters, pagination, the sibling alternative, and the image caveat in order. Slight redundancy with the schema on label semantics keeps it just below 5, 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 still conveys return shape (full text notes, newest-first, `images` field, next_offset pagination) and covers every filter and its interaction. An agent has everything needed to call this tool correctly without follow-up questions.

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 six parameters are already documented, and much of the description's parameter text (ANY-label matching, case-insensitivity, list_contexts for ids, next_offset for pagination) duplicates the schema. It adds mild workflow framing but no syntax or format detail beyond structured fields, making the baseline 3 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?

States a specific verb and resource ('List the user's Contextli voice notes and transcriptions'), plus the ordering and payload ('newest first, with their full text'). It explicitly contrasts itself with the sibling contextli_search_notes, so an agent can disambiguate without reading the 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?

Gives concrete when-to-use cases ('browse recent notes or pull all notes within a date range, context, or label set') and an explicit when-not/alternative rule ('When the user is searching for a specific keyword or phrase, use contextli_search_notes instead'). It also routes to contextli_list_contexts for valid context ids.

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