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

Description adds substantial behavioral detail beyond the minimal annotations (readOnlyHint false, destructiveHint false): each upload is a new record (no overwrite), base64 encoding, 50MB size limit, and error conditions. It also discloses auth-state requirements, which is critical for correct use. No contradiction with annotations.

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 (three sentences) and front-loaded with the primary purpose and scope. Each sentence serves a distinct purpose: core behavior, auth requirement, errors, and related tools. No redundant or vague wording.

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 the tool's complexity (multiple files, base64, auth constraints), the description covers preconditions (auth), failure modes (401/413/422), size limits, and the non-overwrite semantics. It includes related tools for follow-up actions. Absence of an output schema is acceptable since the description doesn't need to describe returns, and the description is sufficient for an agent to invoke correctly.

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?

The schema description covers 100% of the parameter `files`, including its sub-properties (name, mimeType, base64) with details like base64 prefix stripping and 50MB limit. The tool description adds no new parameter-specific guidance, so the baseline of 3 applies.

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'), resource ('files to the authenticated user's Ethora file storage'), and includes the exact endpoint (`POST /v2/files`). It clearly distinguishes from siblings by noting management via `ethora-files-get-v2` / `ethora-files-delete-v2`.

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 clear context: auth requirement (`ethora-user-login` first), specific error codes (401, 413, 422), and a note on related tools for management. Does not explicitly exclude alternate tools or give 'when not to use' guidance, but the context is sufficient for typical selection.

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