SignSimple

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

With no annotations, the description carries the burden and covers the read-only nature ('Check'), returns detailed output (states, progress, URL), and notes the API key requirement. It doesn't mention error behavior or rate limits, but that's acceptable for a simple status tool.

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?

A single, information-dense sentence that includes purpose, output details, and auth requirement with zero redundancy or filler.

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 one-parameter read-only tool with no output schema, the description sufficiently describes all returned data (state, progress, URL) and the required auth, making it complete for an agent to select and 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?

Schema coverage is 100% and the schema already describes envelope_id as returned by send_for_signature. The description reinforces this by referencing 'previously sent' but does not add meaning beyond the schema. Baseline 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?

Description clearly specifies the tool checks document status and enumerates the exact states (sent/completed/declined/expired/voided) and per-recipient progress (pending/viewed/signed), distinguishing it from sibling tools that list or send documents.

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?

States 'previously sent for signature', clearly implying use after send_for_signature, and lists distinct return data. However, it does not explicitly name alternatives or provide when-not-to-use guidance.

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

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 the 25-document limit, the included fields (status, signed-PDF URLs), and the authentication requirement (API key). It implicitly signals a read-only operation via 'List' and does not describe destructive side effects, which is appropriate for this simple tool.

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 two sentences, front-loaded with the core action and scope, and every word adds value. 'Requires a SignSimple API key' is a necessary operational note with no fluff.

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 simplicity (0 params, no output schema, no annotations), the description is complete. It specifies the count (25), the source (connected SignSimple account), the data returned (status, signed-PDF URLs), and the prerequisite (API key). No significant gaps remain.

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 tool has zero parameters, so the description need not explain parameter details. The schema coverage is 100% (vacuously), and the description adds context about the default return set (25 most recent), which is valuable beyond the empty 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 clearly states the verb 'List' and the resource 'documents' with specific scope: the 25 most recent sent from the connected SignSimple account, including status and signed-PDF URLs. This distinguishes it from siblings like list_templates (templates) and get_document_status (single document status).

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 provides clear context for when to use the tool: to list recent documents. However, it does not explicitly mention alternatives or when not to use it (e.g., for single-document status, use get_document_status). This is a minor gap, hence 4 rather than 5.

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

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

No annotations are provided, so the description carries the full burden. It discloses that the tool returns each template's info page and direct PDF URL, and that no API key is required. This is sufficient for a zero-parameter read-only listing tool, though it does not mention rate limits or pagination.

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 two sentences long, front-loaded with the main purpose, and every clause adds value. It efficiently communicates the tool's function, output format, and integration point.

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?

With no parameters, no output schema, and no annotations, the description still provides a complete picture: what it lists, what it returns, how to use the result, and authentication requirements. There are no major gaps for a simple list 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?

There are no parameters, so the baseline is 4. The description adds useful context about the output and how to use it, which compensates for the lack of parameter details.

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 uses a specific verb ('List') and clearly identifies the resource ('SignSimple's free, professionally drafted document templates') with concrete examples. It is easily distinguishable from sibling tools like list_documents, as it focuses on templates rather than sent documents.

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 provides clear context by stating that the returned PDF URL should be passed to send_for_signature, showing how this tool fits into a workflow. It also notes that no API key is needed. However, it does not explicitly mention when not to use this tool or compare it directly with alternatives.

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

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

With no annotations, the description carries the full burden. It discloses that recipients are emailed a secure signing link, fields are placed automatically, and an API key is required. It could mention response format or error handling, but the key side effects are transparent.

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 four sentences, each earning its place: purpose, input requirements, behavioral outcome, and prerequisites/template integration. No redundant or vague filler.

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 (7 params, no annotations, no output schema), the description covers the main operation, input methods, recipient handling, template integration, and API key requirement. It doesn't explicitly state the return value, which is a minor gap, but overall it's complete enough 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?

Schema coverage is 100%, so the baseline is 3. The description adds meaning by explaining that document_url and document_base64 are alternatives, and that templates from list_templates can be passed via document_url. It also clarifies recipient behavior. This exceeds the schema's basic descriptions.

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 tool sends a PDF for legally binding electronic signature via SignSimple, with a specific verb and resource. It differentiates from sibling tools (get_document_status, list_documents, list_templates) which handle status, listing, and templates rather than sending.

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 provides clear context for when to use the tool—when sending a document for signature—and includes a prerequisite (API key) and a cross-reference to list_templates for templates. It doesn't explicitly state when not to use it, but the sibling differentiation is clear enough.

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