Push a file to Stickafile

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

Annotations establish this is a non-read-only, open-world, non-idempotent, non-destructive write. The description goes well beyond them, disclosing that bytes are read from disk and never enter the conversation, that dotfiles/credential-like files are refused, that ~1 minute/GB throughput applies, that there is no resume on retry, and that a missing portal with multiple portals triggers a portal-list response. This is unusually rich behavioral context.

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?

Front-loaded with the core action and return value, then layers edge cases in a logical order. It is long, but nearly every sentence carries actionable constraint (refusals, no-retry, throughput, portal fallback). Slightly verbose with repeated portal-optional phrasing, hence not a full 5.

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 2-parameter upload tool with an output schema and annotations, the description covers the full operational surface: input constraints, credential refusals, timing, retry policy, and the ambiguous multi-portal case. Nothing an agent needs to call it correctly is missing, and the return shape is stated since an output schema exists.

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 coverage is 100%, so the baseline is 3, but the description adds real meaning beyond the schema: path must be absolute and inside the workspace, and portal behavior when omitted (single-portal default vs. multi-portal fallback returning the list), plus 'never invent one.' These operational semantics exceed the field-level schema text.

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: upload a file from disk to a Stickafile portal and return a shareable download link. Clearly separates this from list_portals, which is named only as the source of a portal token. An agent knows exactly what the tool does without opening the schema.

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?

Explicit when-to-use ('when the user wants to send, share, or hand off a file ... or asks for "a link"'), with concrete examples (build, export, report, archive). It also gives operational exclusions: call once per file, wait, do NOT retry automatically because there is no resume, and stop and ask instead. Alternatives and conditions are spelled out.

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