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

No annotations are provided, so the description carries the full burden of behavioral disclosure. It mentions the return content (envelope details, recipient signing status, etc.), which adds value beyond the input schema. However, it lacks critical behavioral details such as required permissions, error handling (e.g., invalid envelope_id), rate limits, or whether this is a read-only operation (implied but not stated). For a tool with zero annotation coverage, this is a significant gap.

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 purpose and followed by return details. Every sentence adds value: the first defines the action, and the second specifies the output content. There is zero waste or redundancy, making it highly efficient and well-structured.

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 low complexity (single required parameter, no output schema, no annotations), the description is minimally adequate. It covers the purpose and return values, but lacks context on usage guidelines, behavioral traits (e.g., permissions, errors), and doesn't fully compensate for the absence of annotations. It's complete enough for basic understanding but has clear gaps for effective agent use.

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 input schema has 100% description coverage, with the 'envelope_id' parameter fully documented as 'The UUID of the envelope to check'. The description doesn't add any parameter-specific information beyond what the schema provides, such as format examples or constraints. With high schema coverage, the baseline score of 3 is appropriate as the description doesn't compensate but doesn't need to.

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's purpose: 'Check the current status of an envelope' specifies the verb (check) and resource (envelope status). It distinguishes from siblings like 'list_envelopes' (list multiple) or 'void_envelope' (modify state), but doesn't explicitly differentiate from 'get_embed_url' which might also retrieve envelope details. The description is specific but lacks explicit sibling differentiation.

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 no guidance on when to use this tool versus alternatives. It doesn't mention prerequisites (e.g., needing an existing envelope ID), exclusions (e.g., not for creating or modifying envelopes), or comparisons to siblings like 'list_envelopes' for bulk status checks. Usage is implied by the purpose but not explicitly stated.

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 provided, the description carries the full burden of behavioral disclosure. It effectively describes the tool's action (create and send for e-signature), output (returns envelope ID and signing URL), and input constraints (PDF options). However, it lacks details on error conditions, rate limits, or authentication requirements, which would be helpful for a mutation 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 efficiently structured in two sentences: the first states the core purpose and output, and the second clarifies the PDF input options. Every sentence adds essential information without redundancy, making it easy to parse and understand quickly.

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 complexity of a mutation tool with no annotations and no output schema, the description does a good job covering the action, output, and key input semantics. However, it could improve by addressing error handling or authentication needs, which are relevant for e-signature operations. The absence of an output schema makes the return value description valuable.

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 schema already documents all parameters thoroughly. The description adds minimal value by mentioning the PDF input alternatives (pdf_path or pdf_base64), but does not provide additional context beyond what's in the schema. This meets the baseline for high schema coverage.

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 specific action ('create an envelope with a PDF document, add a signer, and send it for e-signature'), identifies the resource (envelope), and distinguishes it from siblings like 'send_envelope' (which presumably sends an existing envelope) and 'create_from_template' (which uses templates rather than raw PDFs). It provides a comprehensive overview of the tool's function.

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 implies usage by specifying the document input options (PDF path or base64), but does not explicitly state when to use this tool versus alternatives like 'create_from_template' or 'send_envelope'. No exclusions or prerequisites are mentioned, leaving the agent to infer context from the tool name and description alone.

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 mentions optional pre-filling and immediate sending, but lacks details on permissions, rate limits, error handling, or what happens if 'send_immediately' is false. For a creation tool with mutation implications, this leaves significant behavioral gaps.

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 a single, efficient sentence that front-loads the core purpose and includes key optional features. It avoids redundancy, though it could be slightly more structured for clarity.

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 no annotations, no output schema, and a creation tool with mutation implications, the description is incomplete. It lacks details on return values, error conditions, prerequisites, or how it differs from sibling tools, leaving the agent with insufficient context for reliable use.

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 schema fully documents all 5 parameters. The description adds minimal value beyond the schema, mentioning optional pre-filling and sending, but does not elaborate on parameter usage or constraints. Baseline 3 is appropriate when schema does the heavy lifting.

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 action ('Create an envelope from a template') and resource ('envelope'), with additional context about optional pre-filling and sending. It distinguishes from siblings like 'create_and_send' and 'send_envelope' by emphasizing template-based creation, though not explicitly contrasting them.

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 implies usage when starting from a template, with optional pre-filling and immediate sending, but does not explicitly state when to use this tool versus alternatives like 'create_and_send' or 'send_envelope'. It provides some context but lacks clear exclusions or named 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?

No annotations are provided, so the description carries the full burden of behavioral disclosure. It mentions that webhooks receive POST requests and lists event types, but does not cover critical aspects like authentication requirements, rate limits, error handling, or whether creation is idempotent. This leaves significant gaps for a mutation tool with no annotation coverage.

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 front-loaded with the core purpose in the first sentence, followed by a specific list of event types. Every sentence adds essential information without redundancy, making it efficient and well-structured for quick understanding.

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 no annotations and no output schema, the description provides basic purpose and parameter context but lacks details on behavioral traits, error cases, or return values. For a mutation tool with 3 parameters, this is minimally adequate but leaves gaps in operational understanding, such as how to verify successful creation or handle failures.

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 schema already documents all parameters (url, events, description). The description adds value by listing example event types (e.g., 'envelope.signed'), which provides context beyond the schema's generic description. However, it does not explain parameter interactions or constraints, so baseline 3 is appropriate.

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 'create' and resource 'webhook', specifying its function to 'receive real-time notifications for envelope events'. It distinguishes from siblings like 'list_webhooks' or 'delete_webhook' by focusing on creation, and lists specific event types to clarify scope.

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 implies usage for real-time envelope event notifications but does not explicitly state when to use this tool versus alternatives like polling or other notification methods. It mentions event types but lacks guidance on prerequisites, exclusions, or comparisons to sibling tools like 'list_webhooks' for monitoring existing webhooks.

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 provided, the description carries the full burden of behavioral disclosure. It clearly indicates this is a destructive operation ('Permanently delete') and specifies constraints on envelope states. However, it doesn't mention authentication requirements, error conditions, or what happens after deletion (e.g., confirmation, side effects).

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 extremely concise with two sentences that are front-loaded and zero waste. The first sentence states the core action, and the second adds critical constraints, making every word earn its place.

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 (destructive operation with state constraints), no annotations, and no output schema, the description does well by specifying the permanence and state restrictions. However, it could be more complete by mentioning authentication needs or return values, but it's adequate for the context.

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 coverage is 100%, with the single parameter 'envelope_id' fully documented in the schema as 'The UUID of the envelope to delete'. The description doesn't add any additional parameter information beyond what the schema provides, so it meets the baseline of 3.

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 specific action ('permanently delete') and resource ('an envelope'), and distinguishes it from siblings by specifying which envelope states can be deleted ('Only draft and voided envelopes can be deleted'). This provides precise differentiation from tools like void_envelope or send_envelope.

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 explicitly states when to use this tool ('Only draft and voided envelopes can be deleted'), which provides clear context for usage. It implicitly suggests alternatives for other envelope states (e.g., sent envelopes cannot be deleted, so other tools might be needed). This is explicit guidance on when-not to use it.

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 provided, the description carries the full burden. It discloses key behavioral traits: the tool is destructive ('Delete'), has immediate effect ('stop receiving events immediately'), and requires a specific identifier ('by its ID'). However, it omits details like permissions needed, error conditions, or confirmation prompts.

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 every word earns its place—no redundancy or fluff. It efficiently conveys purpose and immediate effect without unnecessary elaboration.

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 destructive tool with no annotations and no output schema, the description is adequate but incomplete. It covers the basic action and effect, but lacks details on permissions, error handling, or return values. Given the complexity and missing structured data, it should provide more context to be fully helpful.

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 input schema already documents the 'webhook_id' parameter as a UUID. The description adds minimal value beyond this, only reiterating 'by its ID' without providing additional context or examples. Baseline 3 is appropriate given high schema coverage.

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 specific action ('Delete') and resource ('a webhook by its ID'), distinguishing it from siblings like 'create_webhook' or 'list_webhooks'. It precisely defines what the tool does without ambiguity.

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 implies usage when a webhook needs to be removed, but provides no explicit guidance on when to use this versus alternatives (e.g., 'void_envelope' for envelopes) or prerequisites. It lacks context about sibling tools, leaving usage decisions to inference.

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 provided, the description carries full burden but lacks critical behavioral details. It mentions downloading to a local file path but does not disclose permissions needed, file size limits, rate limits, error conditions, or whether the operation is idempotent. The description is functional but misses important operational context for a file-download 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 a single, well-structured sentence that efficiently conveys the tool's purpose, contents, and target resource without any redundant information. It is front-loaded with the core action and appropriately sized for its complexity.

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 moderate complexity (file download with two parameters) and lack of annotations/output schema, the description is minimally adequate. It covers what the tool does but lacks details on behavioral traits, error handling, or output specifics. For a download operation with no structured safety hints, more context would be beneficial.

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 schema already fully documents both parameters (envelope_id as UUID, output_path as local file path). The description adds no additional parameter semantics beyond what the schema provides, such as format examples or path requirements, meeting the baseline for high schema coverage.

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 specific action ('Download a ZIP archive') and resource ('for a completed envelope'), with explicit details on contents ('signed PDF, audit certificate, and all related documents'). It distinguishes from siblings like download_certificate or download_signed by specifying the comprehensive ZIP format and full document set.

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 implies usage context by specifying 'for a completed envelope', suggesting it should only be used after envelope completion. However, it does not explicitly state when NOT to use it (e.g., for pending envelopes) or name alternatives like download_signed for individual documents, leaving some ambiguity.

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 provided, the description carries the full burden. It discloses that the tool downloads a PDF file to a local path and describes the certificate's content (audit trail with timestamps and IP addresses), which adds useful context. However, it doesn't mention potential behavioral aspects like error conditions (e.g., if the envelope isn't completed), file size limits, or authentication requirements.

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 with zero waste: the first sentence states the tool's purpose and key parameters, and the second adds valuable context about the certificate content. It's front-loaded and efficiently structured, with every sentence earning its place.

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 moderate complexity (2 parameters, no output schema, no annotations), the description is reasonably complete. It explains what the tool does and the nature of the output (PDF with audit details), but could improve by addressing error cases or prerequisites more explicitly. The lack of output schema means the description doesn't need to cover return values.

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 schema already documents both parameters (envelope_id as UUID, output_path as local file path). The description adds no additional parameter semantics beyond what the schema provides, such as format details for the UUID or path constraints. This meets the baseline for high schema coverage.

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 specific action ('Download') and resource ('audit certificate PDF for a completed envelope'), distinguishing it from sibling tools like download_archive or download_signed. It specifies the exact document type and its purpose, making the tool's function unambiguous.

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 implies usage by mentioning 'completed envelope,' suggesting it should only be used after an envelope is finished, but it doesn't explicitly state when not to use it or name alternatives. For example, it doesn't clarify if this tool is for audit certificates specifically versus other document types available in sibling tools.

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 provided, the description carries the full burden of behavioral disclosure. It mentions that the tool 'Saves the file to the specified output path', indicating a local write operation, but does not cover other aspects like authentication needs, error handling, rate limits, or what happens if the envelope is not completed. This leaves gaps in behavioral understanding.

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 front-loaded with the core purpose in the first sentence, followed by prerequisites and action details in two concise sentences. Every sentence adds necessary information without waste, making it efficient and well-structured.

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 moderate complexity (a download operation with prerequisites), no annotations, and no output schema, the description is somewhat complete but lacks details on error cases, response format, or system interactions. It covers the basic usage but could benefit from more context for robust agent understanding.

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 input schema has 100% description coverage, so the schema already documents both parameters ('envelope_id' and 'output_path') adequately. The description adds minimal value by implying the envelope must be completed, but does not provide additional syntax or format details beyond what the schema offers, meeting the baseline for high schema coverage.

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 specific action ('Download the signed PDF document') and resource ('for a completed envelope'), distinguishing it from sibling tools like 'download_archive' or 'download_certificate'. It precisely identifies what the tool does without being vague or tautological.

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 this tool by specifying that 'The envelope must be in 'completed' status', which helps guide usage. However, it does not explicitly mention when not to use it or name alternatives (e.g., 'download_archive' for other envelope states), so it falls short of a perfect score.

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 mentions generating a URL for embedding but lacks details on permissions required, rate limits, whether the URL is time-limited, or what happens on failure. For a tool that likely involves authentication and operational constraints, this is insufficient.

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 front-loaded with the core purpose in the first sentence, followed by a concise explanation of usage. Both sentences are necessary and add value without redundancy, making it efficient and well-structured.

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 moderate complexity (generating URLs with potential auth needs), lack of annotations, and no output schema, the description is minimally adequate. It covers the what and why but misses behavioral details like response format or error handling, leaving gaps for the agent.

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 schema already documents both parameters (envelope_id and recipient_id) adequately. The description does not add any additional meaning or context beyond what the schema provides, such as explaining the implications of omitting recipient_id, meeting the baseline for high coverage.

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 specific action ('Generate an embeddable signing URL') and the resource ('for an envelope'), with additional context about its use ('embedded in an iframe for in-app signing experiences'). It distinguishes from siblings like download_signed or void_envelope by focusing on URL generation rather than envelope manipulation or retrieval.

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 implies usage for in-app signing experiences via iframe embedding, but does not explicitly state when to use this tool versus alternatives like send_envelope or check_status. No exclusions or prerequisites are mentioned, leaving the agent to infer context from the tool's purpose.

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 mentions the tool returns 'envelope summaries including titles, statuses, and recipient information,' which adds some behavioral context. However, it lacks details on pagination, rate limits, authentication needs, or whether it's a read-only operation (though implied by 'list'), leaving significant gaps for a tool with no annotation coverage.

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 front-loaded and concise, consisting of two sentences that efficiently convey the tool's purpose and return value. Every sentence earns its place without redundancy, making it easy to parse quickly.

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 moderate complexity (2 parameters, no output schema, no annotations), the description is adequate but incomplete. It covers the basic purpose and return format, but lacks details on behavioral aspects like pagination or error handling. Without annotations or an output schema, more context would be helpful for safe invocation.

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 schema fully documents both parameters. The description adds minimal value beyond the schema by mentioning 'optional filtering by status,' which aligns with the 'status' parameter. It doesn't provide additional semantics for 'limit' or other details, so the baseline score of 3 is appropriate.

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's purpose: 'List your envelopes with optional filtering by status.' It specifies the verb ('list') and resource ('envelopes'), and mentions filtering capability. However, it doesn't explicitly differentiate from sibling tools like 'list_templates' or 'list_webhooks', which prevents a perfect score.

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 implies usage context by mentioning 'optional filtering by status,' suggesting it's for retrieving envelopes with possible status-based selection. However, it doesn't provide explicit guidance on when to use this tool versus alternatives (e.g., 'check_status' for a single envelope or 'list_templates' for templates), nor does it mention prerequisites or exclusions.

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 of behavioral disclosure. While it implies a read-only operation ('List'), it doesn't specify permissions needed, rate limits, pagination behavior, or what the return format looks like (e.g., list of objects with fields). For a tool with zero annotation coverage, this is a significant gap in transparency.

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 appropriately sized with two sentences that efficiently convey the tool's purpose and value. The first sentence states the action and resource, and the second explains what templates are and their use case. There's no wasted text, though it could be slightly more front-loaded with key details.

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 low complexity (2 optional parameters, no output schema, no annotations), the description is minimally adequate. It explains what the tool does but lacks behavioral details like response format or usage context. With no output schema, the agent must infer return values, making this description incomplete for optimal tool selection.

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 schema already documents both parameters ('search' and 'limit') with their types and descriptions. The description adds no additional parameter semantics beyond what the schema provides, which meets the baseline of 3 when the schema does the heavy lifting.

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 resource 'reusable document templates', and explains what templates contain ('pre-placed fields') and their purpose ('used to quickly create envelopes'). However, it doesn't explicitly differentiate from sibling tools like 'create_from_template' or 'list_envelopes', which would require a 5.

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 no guidance on when to use this tool versus alternatives. It doesn't mention when to use 'list_templates' instead of 'list_envelopes' or 'create_from_template', nor does it specify prerequisites or exclusions. This leaves the agent without contextual usage direction.

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 provided, the description carries full burden for behavioral disclosure. It states what the tool does but reveals nothing about permissions needed, rate limits, pagination behavior, response format, or whether this is a safe read operation. 'List all' implies comprehensive retrieval but doesn't clarify scope or constraints.

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 a single, efficient sentence that directly states the tool's function without unnecessary words. It's front-loaded with the core action and resource, making it immediately scannable and easy to understand.

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 tool with no annotations and no output schema, the description is insufficient. It doesn't explain what the output contains (e.g., webhook IDs, URLs, statuses), how results are structured, or any behavioral aspects like pagination. The agent lacks critical context to use this tool effectively.

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 input schema has 0 parameters with 100% coverage, so no parameter documentation is needed. The description appropriately doesn't discuss parameters, focusing instead on the tool's purpose. This meets the baseline for zero-parameter tools.

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 action ('List') and resource ('all configured webhooks for your account'), making the purpose immediately understandable. It doesn't explicitly differentiate from siblings like 'create_webhook' or 'delete_webhook', but the verb 'List' inherently distinguishes it from those mutation operations.

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 no guidance on when to use this tool versus alternatives. It doesn't mention prerequisites, context for listing webhooks, or when other tools like 'create_webhook' or 'delete_webhook' might be more appropriate. The agent must infer usage from the verb alone.

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 provided, the description carries full burden. It discloses key behavioral traits: the envelope must be in 'draft' status and have recipients/fields configured. However, it lacks details on permissions, rate limits, or what happens after sending (e.g., status change).

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 a single, efficient sentence that front-loads the core action ('send a draft envelope for signing') and includes essential prerequisites without waste. Every part earns its place.

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 no annotations and no output schema, the description is adequate for a simple tool with one parameter. It covers the purpose and prerequisites but lacks details on return values or error handling, which would be helpful for a mutation 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?

Schema description coverage is 100%, so the schema already documents the 'envelope_id' parameter as a UUID. The description adds no additional parameter semantics beyond implying it refers to a draft envelope, aligning with the schema but not providing extra value.

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 action ('send a draft envelope for signing') and resource ('envelope'), specifying it must be in 'draft' status. It distinguishes from siblings like 'create_and_send' by focusing on sending existing drafts, but doesn't explicitly contrast with all alternatives.

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 implies usage by stating prerequisites ('draft' status, recipients, fields configured), which helps determine when to use it. However, it doesn't explicitly mention when NOT to use it or name alternatives like 'create_and_send' for creating and sending in one step.

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 provided, the description carries the full burden. It discloses key behavioral traits: it's a destructive action (void/cancel), requires a specific status ('sent'), has side effects (cancels signatures, notifies signers), and includes an optional 'reason' parameter. It doesn't cover error cases or permissions, but provides substantial 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?

Two sentences, zero waste. The first sentence states the purpose and prerequisite, the second explains the outcome. It is front-loaded and appropriately sized for the tool's complexity.

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 no annotations and no output schema, the description is fairly complete for a destructive tool. It covers the action, prerequisites, and effects. However, it lacks details on error handling, return values, or permissions, which could be useful for full contextual understanding.

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 schema already documents both parameters. The description implies the 'envelope_id' must refer to an active envelope in 'sent' status and mentions the 'reason' parameter is optional, adding minimal value beyond the schema. Baseline 3 is appropriate as the schema does the heavy lifting.

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 action ('void/cancel') and resource ('an active envelope'), distinguishing it from siblings like 'delete_envelope' or 'send_envelope'. It specifies the envelope must be in 'sent' status, adding precision beyond the tool 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?

It provides clear context for when to use this tool (envelope in 'sent' status) and mentions the outcome (cancels pending signatures, notifies signers). However, it does not explicitly state when not to use it or name alternatives like 'delete_envelope' for other scenarios.

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