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

Goes well beyond the annotations: it discloses the two-step workflow (pass relative paths, then run the returned command with bash from that folder), the signed-URL mechanism with a 30-minute expiry, the overwrite rule ('A path that exists replaces the file'), and a 50-file cap. This is exactly the operational context an agent needs.

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-loaded with the core action and then layered with workflow, limits, and overwrite behavior. The opening clause about 'the team's context and data, such as priorities, customer lists, and briefs' is slightly promotional but brief enough to keep the description efficient.

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 an output schema present, return values need not be explained; the description instead covers preconditions, execution mechanics, overwrite semantics, and quotas. Nothing material to a correct invocation is missing.

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 schema already documents the single files parameter. The description still adds meaning by tying paths to the folder from which the returned command runs and noting each path becomes the file's name in the space, which is useful framing beyond 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+resource (put files from disk into the team space) and defines what the team space is, including its shared-read purpose. An agent can distinguish it from sibling upload_to_storage and create_upload without opening either 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 an explicit precondition ('Only for a session signed in for a team (whoami shows team)') that tells the agent when the tool is valid. It does not, however, name or compare against the sibling alternatives (upload_to_storage, create_upload), so routing guidance is incomplete.

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