Upload Files/Directory

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

Despite having no annotations, the description discloses a key behavioral trait: the tool refuses to overwrite unless a confirm_code is provided after a conflict preview. This adds valuable transparency about the tool's safety mechanism, which is not apparent from the schema alone. It does not mention other behaviors like sync/async nature or return values, but the overwrite protection is a significant disclosure.

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?

The description is concise and well-structured: two sentences, front-loaded with the main purpose, and the second sentence adds a critical safety detail. No redundant phrasing or filler. Every word earns its place.

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?

The description covers the core purpose and the overwrite refusal behavior, but lacks details about the conflict preview process (e.g., how confirm_code is obtained), whether the operation is synchronous, and expected return values. Given there are no annotations nor output schema, the description carries full burden and is somewhat underspecified for a tool with 4 parameters, though it provides a functional baseline.

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. It only explains confirm_code indirectly via the overwrite condition, but does not clarify the roles of machine, localPath, or remotePath. The meaning of these parameters is left to inference from their names, and the description does not state the relation between local and remote paths.

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?

The description uses a specific verb ('Upload') and resource ('file or directory') and clearly states the destination ('remote machine'). It also distinguishes from sibling tools like 'download' and 'upload-async' by including the overwrite-refusal behavior, which is a unique feature.

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 description does not provide any guidance on when to use this tool versus alternatives such as 'upload-async'. It only states the core action and overwrite behavior, leaving the agent to infer the tool's role. There are no explicit when/when-not conditions or references to sibling tool suitability.

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