Server Quality Checklist

Tool Scores

• sendook_get_webhookA
  3.5/5.0
  Behavior4/5

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

  Annotations declare readOnlyHint=true and idempotentHint=true, and the description adds that it returns URL, events, and timestamps. No contradictions; sufficient context beyond annotations.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is compact (5 lines) and follows a structured Args/Returns format. No redundant phrases, though the format is slightly more verbose than necessary.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness3/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  For a read-only tool with annotations and an output schema, the description minimally covers what is needed. However, it lacks explanation of error handling or when this tool is appropriate among siblings.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters2/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  With 0% schema description coverage, the description only restates the parameter name and type ('webhook_id: Webhook identifier'). No additional meaning or constraints beyond the schema.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states 'Get details of a specific webhook', using a specific verb and resource. This distinguishes it from sibling tools like list (multiple) and test (action).

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines2/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  No guidance on when to use this tool versus alternatives like list_webhooks or test_webhook. No context about prerequisites or 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.

• sendook_send_messageA
  3.6/5.0
  Behavior3/5

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

  Annotations indicate readOnlyHint=false and destructiveHint=false, so the description correctly implies state modification. It adds that the tool sends from an inbox and returns a confirmation, but does not disclose permissions, rate limits, or side effects like sent item storage.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is well-structured with a clear lead sentence, bulleted args, return value, and examples. It is efficient but could be slightly more concise without losing clarity.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness3/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  The description covers most essential aspects (plain text/HTML, attachments, example usage) but lacks usage guidelines and behavioral details. Given the tool's complexity, it is adequate but not fully complete.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters4/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The schema already provides detailed descriptions for each property (e.g., inbox_id, to, subject). The description adds value by summarizing parameters in a clear list and providing concrete examples of usage, aiding comprehension beyond the schema alone.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states the tool's action: 'Send an email message from a Sendook inbox.' It identifies the resource (email message) and distinguishes from siblings like sendook_reply_to_message and other management tools.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines2/5

  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 such as sendook_reply_to_message. It does not mention prerequisites, exclusions, or context where this tool is appropriate.

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

• sendook_test_webhookA
  3.6/5.0
  Behavior3/5

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

  Annotations already declare readOnlyHint, destructiveHint, idempotentHint, and openWorldHint, providing a clear safety profile. The description adds that a test payload is sent and a result is returned, but does not contradict or significantly extend behavioral info.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is relatively concise with a clear first sentence. The Args and Returns sections add some redundancy with the schema but are structured well. Could be slightly more front-loaded.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness3/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  The description covers purpose and basic behavior but lacks detail about the test result string (e.g., possible values), whether the test is asynchronous, or if the webhook must be owned by the user. Given the output schema exists but is not shown, completeness is adequate but not thorough.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The schema fully describes the 'webhook_id' parameter with a description and title. The description repeats the schema without adding new information. With high schema coverage, baseline of 3 is appropriate.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states the tool sends a test event to a webhook endpoint to verify configuration, distinguishing it from sibling tools like create or get webhooks. The verb 'test' and resource 'webhook' are specific.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description implies usage for verifying webhook configuration but does not explicitly state when to use this tool over alternatives or when not to use it. No exclusions or alternative tool names are mentioned.

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

• sendook_list_messagesA
  3.7/5.0
  Behavior3/5

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

  Annotations already declare readOnlyHint=true and idempotentHint=true. The description adds context about return content (subject, labels, timestamps) but no further behavioral details like rate limits or ordering.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is concise with a purpose sentence, return info, and a bullet list of parameters. It front-loads the key action and avoids fluff.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given the tool's moderate complexity (1 parameter object with 4 fields), annotations, and presence of an output schema, the description covers essential information. Missing pagination details but not critical.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The description recaps the parameter names and briefly describes each, but the input schema already provides detailed descriptions (e.g., 'Inbox ID to list messages from'). The description adds minimal new value beyond organization.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states 'List messages in a Sendook inbox' with a specific verb and resource. It differentiates from sibling tools like sendook_get_message (single message) and sendook_list_threads (threads).

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description implies when to use (listing messages with optional filtering) but does not explicitly contrast with siblings or state when not to use, leaving the decision to the agent without clear guidance.

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

• sendook_list_threadsA
  3.7/5.0
  Behavior3/5

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

  Annotations already declare readOnlyHint=true and destructiveHint=false, so the agent knows it's a safe read operation. The description adds context about threads grouping messages and the return format, but does not disclose potential pitfalls like pagination or behavior for non-existent inboxes.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is concise and front-loaded with the main action. The Args section is slightly redundant with the schema but not excessively long. It could be trimmed by relying on the schema, but it's still efficient.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given the simple list operation and the presence of output schema and annotations, the description is nearly complete. It explains the concept of threads and all parameters. Missing details like pagination ordering are minor.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters4/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Although the input schema provides descriptions, the tool description's Args section effectively rephrases and adds clarity (e.g., default limit=20, response_format enum values). It adds value beyond the schema by stating the default and required nature of inbox_id.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states 'List conversation threads in an inbox' with a specific verb and resource, and explains that threads group related messages. This distinguishes it from sibling tools like list_inboxes, list_messages, etc.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines2/5

  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 vs. alternatives. It does not mention when not to use it or recommend sibling tools for specific cases.

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

• sendook_get_messageA
  3.9/5.0
  Behavior4/5

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

  Annotations already declare readOnlyHint=true and destructiveHint=false, confirming a safe read operation. The description adds useful context about returned content (subject, body, labels, timestamps) and output format options, going beyond the annotations.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is well-structured with Args and Returns sections, clear and moderately concise. A minor improvement would be to avoid repeating parameter names already defined in the schema.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  For a simple read operation with rich annotations and a schema, the description covers key aspects: what is returned, required inputs, and format. It does not address error handling or authorization, but these are partially covered by annotations.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The description lists the three parameters with meanings that closely mirror the input schema's descriptions. Since the schema already defines these, the description adds minimal new information. Baseline 3 is appropriate given schema coverage.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states the tool retrieves full details of a specific message, including subject, body, labels, and timestamps. This distinguishes it from sibling tools like 'sendook_list_messages' and 'sendook_get_thread', which have different purposes.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description implies usage when full details of a single message are needed, but it does not explicitly state when to use this tool over alternatives like listing messages or getting threads. There is no 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.

• sendook_get_threadA
  3.9/5.0
  Behavior3/5

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

  Annotations already declare readOnlyHint=true, destructiveHint=false, idempotentHint=true, so the safety profile is covered. The description adds that messages are returned 'in chronological order,' which is useful. No contradictions 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.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is relatively concise: two paragraphs followed by a bullet-list Args section. The primary purpose is stated upfront. The Args section is somewhat redundant with the schema but structurally clear. Every sentence adds value except perhaps the full parameter list could be omitted since it duplicates schema.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given the straightforward nature of a read-only thread retrieval, the description covers what is needed: what it returns (full thread, chronological order, format options). Annotations confirm idempotency and read-only. Output schema exists (though not shown) so return values are documented elsewhere. The description is sufficiently complete for agent usage.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The input schema has descriptions for all parameters, so schema description coverage is effectively high. The description's Args section mostly repeats schema info (inbox_id, thread_id, response_format) with some additional context like 'Output format: markdown or json'. Since the schema already covers parameter meaning, the description adds marginal value beyond providing a structured list. Baseline 3.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states the tool retrieves a full conversation thread with all messages in chronological order, using specific verbs ('Get', 'Returns'). It distinguishes from siblings like sendook_get_message (single message) and sendook_list_threads (list of threads) by specifying 'full thread'.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines4/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description explicitly states it is 'Useful for understanding the full context of a conversation,' implying when to use. While it does not provide explicit when-not-to-use or alternatives, the context of sibling tools like sendook_list_threads and sendook_get_message implies proper usage. Could be improved with explicit prerequisites like 'first use list_threads to obtain thread IDs'.

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

• sendook_list_inboxesA
  3.9/5.0
  Behavior3/5

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

  Annotations already declare readOnlyHint=true, destructiveHint=false, idempotentHint=true, so the agent knows it's safe and idempotent. The description adds that it returns all inboxes with IDs, names, email addresses, and creation dates, but does not disclose other behaviors like pagination or speed. Adds some value beyond annotations.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  Description is roughly three sentences plus an Args/Returns section that somewhat duplicates schema info. It is front-loaded with the main purpose, but the Args/Returns section could be trimmed. Still concise and easy to scan.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  For a simple list operation with one parameter, the description covers purpose, return content, and usage rationale. It does not mention pagination or ordering, but given the open world hint and simplicity, it is fairly complete.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Input schema has one parameter (params) with a property response_format that is described in the schema. The description mentions the parameter and the return formats but does not add significant meaning beyond the schema. With schema coverage high, score is baseline 3.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  Clearly states the verb 'list' and resource 'inboxes in your Sendook organization'. Distinguishes from sibling tools like create, delete, or get individual inbox by focusing on listing all available inboxes.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines4/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  Explicitly says 'Use this to discover available inboxes before sending messages or configuring webhooks', giving clear context. Does not explicitly mention when not to use or provide alternatives, but the use case is well-defined.

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

• sendook_reply_to_messageA
  3.9/5.0
  Behavior3/5

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

  The description adds that it 'maintains the conversation thread context' and 'the reply will be threaded,' which is beyond annotations. However, it does not disclose side effects, authentication needs, rate limits, or error behavior.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is front-loaded with the main purpose and is reasonably concise. The Args section is repetitive but necessary given low schema coverage. Minor redundancy could be trimmed.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  The description includes the return type (confirmation string with reply message ID) and threading behavior. It does not cover error scenarios or prerequisites like message existence, but overall it is adequate for a simple reply tool.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters4/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Despite schema description coverage being 0%, the description's Args section fully enumerates parameters with clear descriptions, including optionality of text and html. This compensates for the lack of schema descriptions.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states 'Reply to an existing message in a conversation thread' with a specific verb and resource. It distinguishes from sibling tools like sendook_send_message by emphasizing threading context.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description implies usage for threaded replies but does not explicitly state when to use this tool versus alternatives (e.g., sendook_send_message for new messages). No prerequisites or exclusions are provided.

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

• sendook_delete_webhookA
  4/5.0
  Behavior4/5

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

  Adds context beyond annotations: 'stops all event deliveries'. Annotations already indicate destructiveHint=true, but description reinforces the irreversible effect and mentions return value.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness5/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  Two sentences plus functional argument/return description. No wasted words; front-loads the action.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Adequate for a delete operation: explains what happens, required parameter, and return type. Missing error handling or permission context, but annotations fill some gaps.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Description repeats what is in the schema ('webhook_id: Webhook to delete') without adding format, constraints, or validation rules. Schema coverage is 0%? Actually the schema has a description for webhook_id, so the description adds minimal value.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  Clearly states 'Delete a webhook subscription' and describes the effect ('Removes the webhook and stops all event deliveries to its endpoint'), distinguishing it from create, get, list, test, and other sibling tools.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  No explicit guidance on when to use or not use this tool versus alternatives. The purpose is implied but lacks context like prerequisites or side-effect warnings.

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

• sendook_list_webhook_attemptsA
  4/5.0
  Behavior4/5

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

  Annotations already declare readOnlyHint, destructiveHint, idempotentHint, openWorldHint. The description adds value by detailing output (successes/failures, status, details) and confirming it shows history, without contradicting annotations.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is concise (4 sentences) and well-structured: purpose, detail, use case, then Args/Returns. No wasted words, though could be slightly more compact.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given the presence of an output schema, the description doesn't need to detail return format. It covers the tool's purpose, input, and use case adequately. Missing details like pagination or recency limits are minor.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters2/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Schema description coverage is 0%, so the description must add meaning. It merely restates the parameter name and type ('webhook_id: Webhook to check attempts for') without adding anything beyond the schema's 'Webhook identifier'. Fails to compensate for low schema coverage.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states the action (list), the resource (recent delivery attempts for a webhook), and the purpose (debugging webhook endpoint issues). It distinguishes from sibling list tools like sendook_list_webhooks by focusing on attempts.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines4/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description explicitly states it is useful for debugging webhook issues, giving clear when-to-use guidance. It does not provide exclusions or alternatives, but the sibling context helps differentiate.

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

• sendook_list_webhooksA
  4/5.0
  Behavior4/5

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

  Annotations already provide readOnlyHint, destructiveHint, idempotentHint, openWorldHint. Description adds the output format (markdown/json) and what information each webhook includes.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness5/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  Description is short, structured with Args/Returns, and every sentence adds value. No unnecessary repetition.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given output schema exists, the description doesn't need to detail return format further. However, it could mention that the return is a string containing the list, which it does.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Schema already fully describes the single parameter 'response_format' with enum and default. Description merely repeats this, adding no extra meaning.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states 'List all configured webhooks' and specifies returns (URLs, events, status). It distinguishes from siblings like sendook_list_inboxes and sendook_get_webhook.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  No explicit when-to-use or when-not-to-use guidance. However, the purpose is straightforward and siblings suggest clear alternatives (create/delete/get).

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

• sendook_create_inboxA
  4.1/5.0
  Behavior4/5

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

  Annotations show readOnlyHint=false (mutation) and destructiveHint=false (not destructive). Description adds that inbox is managed, unique email, independent storage, webhooks, and returns JSON with details. No contradictions.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness4/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  Well-structured with summary, args, returns, examples. Front-loaded with purpose. Slightly verbose in middle paragraph but overall efficient for the complexity.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given simple input (1 param with 2 optional properties) and output schema implied, description covers purpose, parameters, return format, and examples. Lacks error handling discussion but acceptable for this tool.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Schema descriptions for name and email are already detailed and cover 100% of properties. Description adds examples but does not significantly extend beyond schema. Baseline 3 is appropriate.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  Clearly states 'Create a new inbox for an AI agent to send and receive emails' with specific verb and resource. Distinguishes from sibling tools like get_inbox and list_inboxes. Includes key differentiator: each inbox has independent storage and webhooks.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines4/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  Provides examples for creating with name or custom email, and notes email auto-generation. Implicitly guides when to use (inbox creation) but lacks explicit when-not-to-use or alternatives among siblings.

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

• sendook_get_inboxA
  4.1/5.0
  Behavior4/5

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

  Annotations already declare readOnlyHint=true. The description adds value by specifying return fields (id, name, email, createdAt) and confirms the read-only nature. No contradictions.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness5/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is concise with a clear docstring format. Every sentence adds value, no fluff.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness5/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given the simple read-only operation, the description covers purpose, parameter, and return fields. Annotations provide behavioral context. Complete for this tool.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The input schema already describes the parameter well; the description repeats the structure without adding new semantic details. Schema description coverage is effectively high, so baseline 3 is appropriate.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description states 'Get details for a specific inbox' with clear verb and resource. It distinguishes from sibling tools like sendook_list_inboxes by specifying 'specific inbox'.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines3/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  No explicit when-to-use or when-not-to-use guidance is provided. Usage is implied but not explicitly differentiated from alternatives.

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

• sendook_delete_inboxA
  4.2/5.0
  Behavior4/5

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

  Annotations already provide destructiveHint=true and readOnlyHint=false. The description adds valuable behavioral context: it revokes sending access, archives all historical messages, and the address stops receiving messages. It does not contradict annotations. It could mention if the action is reversible or what happens to archived messages, but overall strong.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness5/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is efficient: a short purpose statement, a warning in all caps, and clearly labeled Args/Returns sections. Every sentence adds value, no fluff.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  Given the tool's simplicity (one parameter, clear action), the description is nearly complete. It covers the action, consequences, parameter, and return type. It could optionally mention idempotency (implied by delete) or error handling, but these are not critical gaps.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters3/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  The description repeats the parameter 'inbox_id' as 'the inbox identifier to delete' but adds no meaning beyond the schema, which already provides a description and example. Schema description coverage is considered 0% per context, but the schema itself has a description. With minimal addition, baseline 3 is appropriate.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states 'Delete an inbox and archive its messages' with a specific verb and resource. It distinguishes from sibling tools like sendook_get_inbox and sendook_create_inbox by focusing on deletion, and includes a warning about consequences, leaving no ambiguity.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines4/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description includes a warning that revoking sending access and archiving messages makes this action permanent, implying when to use (when you want to permanently remove an inbox). However, it does not explicitly state when not to use or compare with alternatives like a disable option, but given no such sibling exists, it's nearly complete.

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

• sendook_create_webhookA
  4.4/5.0
  Behavior4/5

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

  The description discloses that the tool creates a webhook (a mutation), and adds constraints on the endpoint (HTTPS, response time) beyond what annotations provide. No contradictions with annotations (readOnlyHint=false, destructiveHint=false). However, it does not mention side effects like overwriting existing webhooks or rate limits.

  Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

  Conciseness5/5

  Is the description appropriately sized, front-loaded, and free of redundancy?

  The description is concise with a clear structure: purpose, constraints, event list, and parameter/return summary. Every sentence adds value, no fluff.

  Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

  Completeness4/5

  Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

  The tool has one parameter (params) with full schema detail and an output schema exists. The description explains the return type ('str: Created webhook details including id and subscribed events'), which is sufficient for an agent to use the tool, though the exact format is not detailed.

  Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

  Parameters4/5

  Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

  Although schema coverage is 0%, the description covers both parameters ('url' and 'events') with their meanings, complementing the schema's own descriptions. It adds context like HTTPS requirement for url and event list examples.

  Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

  Purpose5/5

  Does the description clearly state what the tool does and how it differs from similar tools?

  The description clearly states it creates a webhook for real-time event notifications, with a specific verb ('Create') and resource ('webhook'). It lists available event types, making the purpose very clear and distinct from sibling tools like delete or list.

  Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

  Usage Guidelines4/5

  Does the description explain when to use this tool, when not to, or what alternatives exist?

  The description provides explicit requirements (HTTPS endpoint, 15-second timeout, 2xx response) and lists available events, which helps the agent understand when to use it. It does not explicitly exclude alternatives, but the sibling tools are different operations, so context is clear.

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