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

Annotations already declare destructiveHint=true, idempotentHint=true and readOnlyHint=false, so the safety profile is covered. The description adds genuinely useful non-annotation context in the required write scope, but says nothing about what a destructive update replaces, whether omitted fields are preserved, or whether the file payload itself changes.

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 short sentences, zero filler, with the operation and the targeting key front-loaded before the permission requirement. Nothing in it is redundant or padded.

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 7-parameter destructive mutation with no output schema, the description covers identity and authorization but omits whether this is a partial or full replacement, what happens to unspecified fields, and what is returned. Annotations carry the safety story, but the mutational semantics remain underspecified.

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 100%, so all seven parameters (id, file_name, file_path, file_size, file_type, contract_id, uploaded_by) are already documented in the schema. The description only restates that the target is identified by ID, adding no new semantics, so the baseline 3 applies.

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 (Update) and resource (contract document) plus the lookup key (by ID), so the action is unambiguous. However, it does not differentiate itself from the many neighboring update_* tools (e.g. update_contract, update_asset_document) beyond the resource name in the tool name itself.

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?

No when-to-use guidance, no mention of alternatives such as update_contract or create_contract_document, and no indication of when this should be preferred over bulk_update. The only contextual hint is 'by ID', which is a targeting detail rather than usage guidance.

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