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

Annotations already declare readOnlyHint=true, destructiveHint=false, and openWorldHint=false, so the description's 'Read-only' merely confirms them. Beyond that it adds real context: the workspace scoping, the deterministic sort order, the fact that holder matching is case-insensitive, and the exact return envelope {items,total,has_more}.

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, front-loaded with scope and sort before the filter inventory, with zero filler. The semicolon-chained filter list is dense but scannable; a slightly clearer separation of filters from paging would cost nothing.

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 seven-parameter, zero-required read tool with no output schema, the description covers scope, sort, filter semantics, paging, and the return envelope — enough to call it correctly. The residual gaps are the unexplained 'kind' values and the unstated boundary against list_documents.

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 0%, so the description must carry parameter meaning, and it does for six of seven: holder is case-insensitive, expiring_within_days is defined as 'within N days from today', from/to are pinned to YYYY-MM-DD valid_until bounds, and limit/offset are framed as paging. The 'kind' parameter is named but never explained, leaving its accepted values ambiguous with no enum in the schema.

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 plus scope ('caller's tracked documents from their active workspace') and a defined sort ('valid_until ascending, soonest expiry FIRST'). It implies a distinction from the sibling list_documents by repeatedly using 'tracked', but never explicitly contrasts the two, so an agent still has to infer that difference.

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?

Usage is implied through the filter list — an agent can work out that expiring_within_days is for expiry monitoring and from/to for range scans. However, there is no explicit when-to-use or when-not-to-use guidance, and no pointer to add_tracked_document, get_tracked_document, or list_documents as alternatives.

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