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insert_smime_info

Upload S/MIME configuration for a Gmail send-as alias to enable email encryption and digital signatures.

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

  • The handler function for the 'insert_smime_info' tool, registered via server.tool(). It calls the Gmail API to insert S/MIME info for a send-as alias using handleTool wrapper. Includes inline schema definition.
    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)
        })
      }
    )
  • Input schema (Zod) for the 'insert_smime_info' tool, defining parameters sendAsEmail, encryptedKeyPassword, and pkcs12.
      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")
    },
  • src/index.ts:1261-1274 (registration)
    Registration of the 'insert_smime_info' tool using server.tool(), including description, schema, and handler.
    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)
        })
      }
    )
  • Shared helper function 'handleTool' used by 'insert_smime_info' and other tools for authentication, Gmail client creation, and error handling.
    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) {
        // Check for specific authentication errors
        if (
          error.message?.includes("invalid_grant") ||
          error.message?.includes("refresh_token") ||
          error.message?.includes("invalid_client") ||
          error.message?.includes("unauthorized_client") ||
          error.code === 401 ||
          error.code === 403
        ) {
          return formatResponse({
            error: `Authentication failed: ${error.message}. Please re-authenticate by running: npx @shinzolabs/gmail-mcp auth`,
          });
        }
    
        return formatResponse({ error: `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 states this is an 'insert/upload' operation, implying a write/mutation, but fails to mention critical aspects like required permissions, whether it overwrites existing configs, error handling, or any rate limits. This leaves significant gaps for an agent to understand the tool's behavior.

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 is appropriately sized and front-loaded, 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?

Given that this is a mutation tool with no annotations and no output schema, the description is incomplete. It lacks details on behavioral traits (e.g., permissions, side effects), output format, or error conditions, which are crucial for an agent to use it effectively in context.

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 description coverage is 100%, meaning all parameters are documented in the input schema. The description adds no additional semantic details about the parameters beyond what's in the schema, so it meets the baseline score of 3 without compensating value.

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 'set_default_smime_info' or 'delete_smime_info', which would be needed for 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.

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 like 'set_default_smime_info' or 'delete_smime_info', nor does it mention prerequisites or exclusions. It merely restates the action without contextual usage information.

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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