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insert_smime_info

Upload S/MIME certificates to configure email encryption for specific sender aliases in Gmail, enabling secure message signing and encryption.

Instructions

Insert (upload) the given S/MIME config for the specified send-as alias

Input Schema

TableJSON Schema
NameRequiredDescriptionDefault
sendAsEmailYesThe email address that appears in the 'From:' header
encryptedKeyPasswordYesEncrypted key password
pkcs12YesPKCS#12 format containing a single private/public key pair and certificate chain

Implementation Reference

  • src/index.ts:1247-1260 (registration)
    Registration of the 'insert_smime_info' tool, including schema and handler function, using the MCP server.tool method.
    server.tool("insert_smime_info",
      "Insert (upload) the given S/MIME config for the specified send-as alias",
      {
        sendAsEmail: z.string().describe("The email address that appears in the 'From:' header"),
        encryptedKeyPassword: z.string().describe("Encrypted key password"),
        pkcs12: z.string().describe("PKCS#12 format containing a single private/public key pair and certificate chain")
      },
      async (params) => {
        return handleTool(config, async (gmail: gmail_v1.Gmail) => {
          const { data } = await gmail.users.settings.sendAs.smimeInfo.insert({ userId: 'me', sendAsEmail: params.sendAsEmail, requestBody: params })
          return formatResponse(data)
        })
      }
    )
  • Handler function that uses handleTool to validate auth, create Gmail client, insert S/MIME info via Gmail API, and format response.
    async (params) => {
      return handleTool(config, async (gmail: gmail_v1.Gmail) => {
        const { data } = await gmail.users.settings.sendAs.smimeInfo.insert({ userId: 'me', sendAsEmail: params.sendAsEmail, requestBody: params })
        return formatResponse(data)
      })
    }
  • Zod schema defining input parameters: sendAsEmail, encryptedKeyPassword, and pkcs12 for the insert_smime_info tool.
    {
      sendAsEmail: z.string().describe("The email address that appears in the 'From:' header"),
      encryptedKeyPassword: z.string().describe("Encrypted key password"),
      pkcs12: z.string().describe("PKCS#12 format containing a single private/public key pair and certificate chain")
    },
  • Shared helper function handleTool used by insert_smime_info (and other tools) to handle OAuth2 authentication, Gmail client creation, and API call execution.
    const handleTool = async (queryConfig: Record<string, any> | undefined, apiCall: (gmail: gmail_v1.Gmail) => Promise<any>) => {
      try {
        const oauth2Client = queryConfig ? createOAuth2Client(queryConfig) : defaultOAuth2Client
        if (!oauth2Client) throw new Error('OAuth2 client could not be created, please check your credentials')
    
        const credentialsAreValid = await validateCredentials(oauth2Client)
        if (!credentialsAreValid) throw new Error('OAuth2 credentials are invalid, please re-authenticate')
    
        const gmailClient = queryConfig ? google.gmail({ version: 'v1', auth: oauth2Client }) : defaultGmailClient
        if (!gmailClient) throw new Error('Gmail client could not be created, please check your credentials')
    
        const result = await apiCall(gmailClient)
        return result
      } catch (error: any) {
        return `Tool execution failed: ${error.message}`
      }
    }
Behavior2/5

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 implies a write operation ('insert/upload') but doesn't specify permissions needed, whether it's idempotent, what happens on failure, or any rate limits. This leaves significant gaps 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.

Conciseness5/5

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

The description is a single, efficient sentence that directly states the tool's purpose without unnecessary words. It's front-loaded and wastes no space, making it easy to parse quickly.

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

Completeness2/5

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

For a mutation tool with no annotations and no output schema, the description is insufficient. It lacks details on behavioral aspects like error handling, side effects, or return values, leaving the agent with incomplete information to use the tool effectively.

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 description coverage is 100%, so the input schema already documents all three parameters thoroughly. The description doesn't add any additional meaning or context beyond what the schema provides, such as explaining relationships between parameters or usage examples, 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.

Purpose4/5

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

The description clearly states the action ('insert/upload') and the resource ('S/MIME config for the specified send-as alias'), making the purpose evident. However, it doesn't explicitly differentiate from sibling tools like 'delete_smime_info' or 'set_default_smime_info', which would be needed for a score of 5.

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 is provided on when to use this tool versus alternatives like 'delete_smime_info' or 'set_default_smime_info', nor any prerequisites or context for its application. The description merely restates the purpose without offering usage instructions.

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

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