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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:1228-1241 (registration)
    Registration of the 'insert_smime_info' MCP tool, including input schema definition using Zod and the handler function that wraps the Gmail API call to users.settings.sendAs.smimeInfo.insert with OAuth handling.
    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)
        })
      }
    )
  • Zod schema defining the input parameters for the insert_smime_info tool: 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")
    },
  • Handler implementation that uses the shared handleTool to authenticate and execute the Gmail API insertion of S/MIME info.
    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 used by all tools, including insert_smime_info, to handle OAuth2 client creation, credential validation, Gmail client initialization, 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) {
        return `Tool execution failed: ${error.message}`
      }
    }
Behavior2/5

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 implies a write operation ('insert/upload') but doesn't disclose behavioral traits such as required permissions, whether this overwrites existing configs, error conditions, or side effects. For a mutation 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.

Conciseness5/5

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

The description is a single, efficient sentence with zero waste—it directly states the tool's action and target without unnecessary details. It's appropriately sized and front-loaded, earning its place.

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 the complexity of a mutation tool with no annotations and no output schema, the description is incomplete. It lacks information on behavioral aspects (e.g., permissions, effects) and doesn't compensate for the absence of structured data, making it inadequate for safe and effective use by an AI agent.

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%, so the schema already documents all three parameters thoroughly. The description adds no additional meaning beyond what's in the schema (e.g., it doesn't explain parameter relationships or usage nuances), meeting the baseline of 3 when schema does the heavy lifting.

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 require more specific context about when to use each.

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 context for usage. It lacks explicit when/when-not statements or named alternatives.

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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