upload_file

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

No annotations are provided, so the description carries the burden. It discloses performance characteristics (base64 is extremely slow and fills the context window), the server-side read behavior for file_path, and the existence of a fallback for remote deployments. It doesn't explicitly state whether the upload is a write/destructive operation, but the verb 'upload' and the context make that clear enough.

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 compact and front-loaded with the primary use case, then the key decision rule, then the fallback. Every sentence earns its place. Slight redundancy between the description and the schema's file_content_base64 description, but the emphasis is intentional and useful.

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?

For a 5-parameter tool with no output schema and no annotations, the description covers the main decision (file_path vs base64), the attachment semantics, and how to find valid object_type_id values. It doesn't describe the response format, but with no output schema that is a minor gap. It also doesn't mention whether object_id is required when attaching, but the schema marks no parameters as required.

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 100%, so the baseline is 3. The description adds value by explaining the trade-off between file_path and file_content_base64, and by giving an example object_type_id (7 = Unit). It also clarifies that file_name is an override and inferred from file_path if omitted, which is 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 states a specific verb ('Upload a file to Rentvine') and resource, and clarifies optional attachment to a work order, property, lease, or unit. It distinguishes itself from sibling tools like get_file and download_file by focusing on upload, and from list_attachments by focusing on creation.

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 gives explicit when-to-use guidance: use file_path for local files, use file_content_base64 only for remote/HTTP deployments with no shared filesystem, and use list_object_types to get valid object_type_id values. It also explicitly says NEVER use file_content_base64 for local files, which is strong exclusionary guidance.

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