target_upload_file

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

With no annotations, the description carries the burden. It discloses that content must be base64-encoded, method options, encoding options, and optional SHA256 checksum. However, it does not mention what happens on failure, required session state, or permission implications.

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 front-loaded with the tool's purpose, followed by a well-organized parameter list. It is efficient without unnecessary repetition, though it could be slightly more condensed.

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 no annotations and an output schema exists, the description covers the core purpose and parameters. However, it lacks details on prerequisites (e.g., session must be active), error handling, and file overwrite behavior, leaving some gaps for a mutation tool.

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 fully defines all 6 parameters with clear context beyond the titles. Each parameter's role (e.g., 'active session ID', 'destination path', 'transfer method') is explained, enabling correct parameter usage.

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 the verb 'upload' and the resource 'content to a target via an active session (SSH or reverse shell)', distinguishing it from sibling tools like ssh_session_upload_content and reverse_shell_upload_content by indicating it supports both methods via a parameter.

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 implies usage for uploading files via active sessions but does not explicitly guide when to use this tool over its siblings (e.g., for specific session types use the specialized upload tools). No when-not-to-use or alternative suggestions are provided.

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