ssh_upload

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

With no annotations provided, the description fully discloses behavioral traits: overwriting existing files, non-idempotent nature, no backup creation, no sudo, and server security mode restrictions. No contradictions.

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?

Concise paragraph with no redundant sentences. Key information is front-loaded: action, target, and overwriting behavior. Every sentence adds necessary detail.

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?

Given three required parameters and no output schema, the description covers all essential aspects: operation, side effects, prerequisites, constraints, security, and alternative. No gaps.

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 covers 100% of parameters with basic descriptions. The tool description adds valuable context like 'over SFTP', 'overwriting', and 'requires local file to exist', enhancing the meaning 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?

The description clearly states 'Uploads one local file to a remote destination path over SFTP' with a specific verb and resource. It distinguishes from sibling tools by mentioning 'For directory trees use ssh_sync instead'.

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?

Explicitly states when to use (single file upload), prerequisites (local file must exist, remote path writable), blocking conditions (readonly/restricted servers), and an alternative (ssh_sync for directories).

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