List files

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

Annotations already declare readOnlyHint=true and destructiveHint=false, lowering the bar. The description does add real value by disclosing permission-dependent source switching (course index vs linked-content fallback, common for students) and default ordering, but says nothing about pagination, result limits, or what the returned records look like.

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 dense, front-loaded sentences with no filler — the resource and ordering come first. The trailing "like canvas_list_linked_files" clause is slightly awkward but carries genuine information about fallback behavior.

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 and zero schema coverage on two parameters, the description should carry more weight. It covers the interesting behavioral wrinkle (role-based source selection) but leaves the search filter and returned fields entirely unaddressed, so an agent still has gaps before calling.

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 compensate and does not. It never mentions the `search` parameter at all, leaving an agent to guess at its filtering semantics, scope, and interaction with the newest-first ordering; `course_id` is only obliquely implied by "in a course."

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?

Names the resource (files in a course) and a meaningful scope detail (newest-first ordering), which distinguishes it from generic listing tools. The verb "list" comes from the name rather than the description, and the closing comparison to canvas_list_linked_files blurs the boundary rather than sharpening it.

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 fallback sentence implies a condition (role-based visibility determines which source is used), which is useful context, but it never states when an agent should choose this tool over canvas_list_linked_files — it only says the two behave similarly. Selection guidance is implied, not explicit.

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