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

Annotations declare write/non-destructive/non-idempotent/non-open-world, so safety is already covered. The description adds behavior the annotations cannot convey: keywords are normalized (stored without spaces, in capitals), URLs are validated as https, and file deliverables require a prior upload_media round-trip whose URL is reused. It does not describe the failure modes or what the created record looks 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?

Roughly four sentences, purpose front-loaded, followed by validation and the file-upload workflow, ending with a docs link. Every sentence carries information; the parenthetical examples are slight padding but not wasteful. Tight enough for a 7-parameter tool.

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 could say what is returned after creation, and it does not; it also says nothing about duplicate-handling beyond the schema's idempotencyKey. Otherwise it covers purpose, validation, the file workflow, keyword normalization, and workspace scoping is handled by the schema, so an agent has what it needs to call it correctly.

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 the baseline is 3, but the description genuinely adds semantics: it explains the kind="file" branch and how url must be sourced from upload_media in that case, and it explains that keyword is transformed rather than stored verbatim. These are cross-parameter relationships the per-field schema text does not state.

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?

Specific verb+resource ('Add a deliverable a DM can send') with concrete examples (guide, template, file, link) and an explicit framing of what this resource is for — the thing a keyword call-to-action promises. That framing cleanly separates it from list_dm_resources/update_dm_resource/delete_dm_resource and from create_comment_to_dm, which configures the keyword rather than the deliverable.

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 operational conditions: links must be https, and for a FILE the agent must first call upload_media and pass its returned url with kind "file". This is real when/how guidance tied to an alternative tool. It stops short of stating exclusions (e.g., use update_dm_resource to modify an existing resource instead of creating a duplicate), so it is not a full 5.

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