winrm_upload

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

Annotations already declare destructiveHint=true and openWorldHint=true, so the safety profile is covered. The description adds non-obvious operational context the annotations cannot convey: the feature is gated behind an operator-set root directory, and local paths are resolved relative to it. It stops short of stating overwrite behavior on the remote path, which matters for a destructive-labeled write.

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 sentences, no waste, with the primary action first and the path-semantics constraints following. Every clause carries information the agent needs.

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?

An output schema exists, so return values need no explanation, and the destination/source path semantics are covered. For a destructive, open-world file transfer with no schema descriptions on five parameters, missing details on overwrite behavior and how to target a host leave it only adequate.

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 carries the burden, and it does explain the two required parameters well (local relative to WINRM_MCP_LOCAL_ROOT, remote an absolute Windows path). But three optional parameters — connection, saved_host, inventory_scope — remain entirely undocumented in both schema and description, leaving a real gap.

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 and resource ('Copy a local file to the Windows host'), which is unambiguous and implicitly opposite to the sibling winrm_download. It does not explicitly name the sibling or its inverse condition, so differentiation relies on the agent inferring direction from the name.

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?

Provides one genuinely useful prerequisite: transfer is disabled unless the operator sets WINRM_MCP_LOCAL_ROOT. However, it gives no guidance on when to pick this over winrm_download, nor how the optional connection/saved_host/inventory_scope parameters should be chosen to reach a host.

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