apple-mail-mcp 1.5.6 → 1.6.0

package/README.md

@@ -192,8 +192,9 @@ Send a new email immediately.
 | `body` | string | Yes | Email body (plain text) |
 | `cc` | string[] | No | CC recipients |
 | `bcc` | string[] | No | BCC recipients |
-| `account` | string | No | Send from specific account |
+| `account` | string | No | Send from specific account (with `transport: "smtp"`, overrides the From address) |
 | `attachments` | string[] | No | Absolute file paths to attach, max 20 files (e.g., `["/Users/me/report.pdf"]`) |
+| `transport` | `"applescript"` \| `"smtp"` | No | Send transport (default `"applescript"`). Use `"smtp"` to send clean MIME directly, avoiding the macOS 15+ Mail.app `<blockquote>` wrapping — see [SMTP transport](#smtp-transport) |
 
 **Example:**
 ```json
@@ -206,6 +207,48 @@ Send a new email immediately.
 }
 ```
 
+##### SMTP transport
+
+On macOS 15+ (Sequoia/Tahoe), Mail.app wraps any AppleScript-injected body in
+`<blockquote type="cite">` under the `Apple-Mail-URLShareWrapperClass` template,
+so emails sent through the default `applescript` transport render to recipients
+as if they were quoted/forwarded (Apple radar **FB11734014**, open since
+Ventura). Passing `transport: "smtp"` bypasses Mail.app entirely and submits
+clean MIME via SMTP.
+
+Configure SMTP via environment variables on the MCP server. The password is
+read from the macOS **Keychain** by default, so no secret goes in config:
+
+| Variable | Required | Default | Description |
+|----------|----------|---------|-------------|
+| `APPLE_MAIL_MCP_SMTP_HOST` | Yes | — | SMTP server hostname (e.g. `smtp.fastmail.com`) |
+| `APPLE_MAIL_MCP_SMTP_USER` | Yes | — | SMTP username |
+| `APPLE_MAIL_MCP_SMTP_PORT` | No | `465` if secure, else `587` | SMTP port |
+| `APPLE_MAIL_MCP_SMTP_SECURE` | No | `false` | `true` for implicit TLS (port 465); otherwise STARTTLS |
+| `APPLE_MAIL_MCP_SMTP_FROM` | No | = user | From address |
+| `APPLE_MAIL_MCP_SMTP_PASSWORD` | No | — | Password (if set, used instead of the Keychain) |
+| `APPLE_MAIL_MCP_SMTP_KEYCHAIN_SERVICE` | No | = host | Keychain item service/server name |
+| `APPLE_MAIL_MCP_SMTP_KEYCHAIN_ACCOUNT` | No | = user | Keychain item account |
+
+Store the password in the Keychain once (an app-specific password for Gmail/
+iCloud), e.g.:
+
+```bash
+security add-internet-password -s smtp.fastmail.com -a you@example.com -w
+```
+
+Then send:
+```json
+{
+  "to": ["colleague@company.com"],
+  "subject": "Standings",
+  "body": "Plain body — no blockquote wrapping.",
+  "transport": "smtp"
+}
+```
+
+The default `applescript` transport is unchanged; SMTP is opt-in per call.
+
 ---
 
 #### `send-serial-email`
@@ -742,6 +785,17 @@ The entrypoint is written as:
 | Attachment save path restrictions | `save-attachment` only allows saving to home directory, `/tmp`, `/private/tmp`, and `/Volumes`; path traversal is blocked |
 | Attachment count limit | `send-email` and `create-draft` accept a maximum of 20 file attachments |
 
+### Mail.app `<blockquote>` wrapping on macOS 15+ (workaround in v1.6.0)
+
+On macOS 15+ Mail.app wraps AppleScript-injected message bodies in
+`<blockquote type="cite">` under the `Apple-Mail-URLShareWrapperClass` template,
+so mail sent via the default `applescript` transport renders to recipients as
+quoted/forwarded content (Apple radar **FB11734014**, open since Ventura, no
+fix). Since v1.6.0, `send-email` accepts `transport: "smtp"` to bypass Mail.app
+and send clean MIME directly — see [SMTP transport](#smtp-transport). The
+AppleScript path is still the default and still exhibits Apple's wrapping.
+([#12](https://github.com/sweetrb/apple-mail-mcp/issues/12))
+
 ### Reply / Forward from Background Processes (Fixed in v1.4.0)
 
 Prior to v1.4.0, `reply-to-message` and `forward-message` would send messages with **empty body text** when the MCP server ran as a background process (e.g., spawned via `execSync` from Node.js, which is how Claude Code invokes it).

package/build/index.js

@@ -24,6 +24,8 @@ import { McpServer } from "@modelcontextprotocol/sdk/server/mcp.js";
 import { StdioServerTransport } from "@modelcontextprotocol/sdk/server/stdio.js";
 import { z } from "zod";
 import { AppleMailManager } from "./services/appleMailManager.js";
+import { sendViaSmtp } from "./services/smtpMailer.js";
+import { createSerialGate } from "./utils/serialize.js";
 // =============================================================================
 // Shared Validation Schemas
 // =============================================================================
@@ -84,17 +86,32 @@ function errorResponse(message) {
     };
 }
 /**
- * Wraps a tool handler with consistent error handling.
+ * Serial execution gate for AppleScript-backed tool calls (issue #11).
+ *
+ * Concurrent MCP tool calls are funneled through this single gate so only one
+ * osascript invocation hits Mail.app's single-threaded AppleScript dispatch at
+ * a time, with a short settle delay between calls so the dispatch queue drains.
+ * Without it, a concurrent batch races into Mail.app, the later calls blow past
+ * their timeouts, and Mail.app is left half-recovered for the next batch.
+ */
+const serializeAppleScript = createSerialGate();
+/**
+ * Wraps a tool handler with consistent error handling, serialized through the
+ * AppleScript gate so concurrent MCP tool calls don't race into Mail.app (#11).
+ * Handlers may be synchronous or async (the SMTP send path in send-email is
+ * async), so the handler result is awaited inside the gate.
  */
 function withErrorHandling(handler, errorPrefix) {
     return async (params) => {
-        try {
-            return handler(params);
-        }
-        catch (error) {
-            const message = error instanceof Error ? error.message : "Unknown error";
-            return errorResponse(`${errorPrefix}: ${message}`);
-        }
+        return serializeAppleScript(async () => {
+            try {
+                return await handler(params);
+            }
+            catch (error) {
+                const message = error instanceof Error ? error.message : "Unknown error";
+                return errorResponse(`${errorPrefix}: ${message}`);
+            }
+        });
     };
 }
 // =============================================================================
@@ -176,12 +193,25 @@ server.tool("send-email", {
         .max(20, "Cannot attach more than 20 files")
         .optional()
         .describe("Absolute file paths to attach (e.g., ['/Users/me/report.pdf'])"),
-}, withErrorHandling(({ to, subject, body, cc, bcc, account, attachments }) => {
+    transport: z
+        .enum(["applescript", "smtp"])
+        .optional()
+        .describe("Send transport. 'applescript' (default) sends through Mail.app. " +
+        "'smtp' submits clean MIME directly via SMTP, avoiding the macOS 15+ " +
+        "Mail.app <blockquote> wrapping (issue #12); requires APPLE_MAIL_MCP_SMTP_* env config."),
+}, withErrorHandling(async ({ to, subject, body, cc, bcc, account, attachments, transport }) => {
+    const attachInfo = attachments?.length ? ` with ${attachments.length} attachment(s)` : "";
+    if (transport === "smtp") {
+        const result = await sendViaSmtp({ to, subject, body, cc, bcc, from: account, attachments });
+        if (!result.success) {
+            return errorResponse(result.error ?? "Failed to send email via SMTP.");
+        }
+        return successResponse(`Email sent via SMTP to ${to.join(", ")}${attachInfo}`);
+    }
     const success = mailManager.sendEmail(to, subject, body, cc, bcc, account, attachments);
     if (!success) {
         return errorResponse("Failed to send email. Check Mail.app configuration.");
     }
-    const attachInfo = attachments?.length ? ` with ${attachments.length} attachment(s)` : "";
     return successResponse(`Email sent to ${to.join(", ")}${attachInfo}`);
 }, "Error sending email"));
 // --- send-serial-email ---

package/build/services/appleMailManager.d.ts.map

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package/build/services/appleMailManager.js

@@ -789,13 +789,11 @@ export class AppleMailManager {
     // Discussion: https://forums.macrumors.com/threads/applescript-creating-a-
     //   new-message-in-mail-app-is-causing-weird-formatting-issues.2385052/
     //
-    // Workaround for callers who need clean emails today: use SMTP directly
-    // (Python smtplib). See e.g. sweetrb/nhl-bracket-tracker's send_email.py.
-    //
-    // Proper fix is probably to abandon `make new outgoing message` and either:
-    //   1. Build the .emlx file ourselves and drop it into a Drafts mailbox.
-    //   2. Switch to smtplib-style direct send with Keychain-stored creds.
-    //   3. Use Mail.app's NSSharingService rather than AppleScript.
+    // FIX (v1.6.0): send-email now accepts `transport: "smtp"`, which bypasses
+    // Mail.app and submits clean MIME directly via nodemailer (creds from the
+    // Keychain). See src/services/smtpMailer.ts. This AppleScript path remains
+    // the default for back-compat and for users who don't configure SMTP, so the
+    // wrapping behavior below is unchanged for them.
     // Tracking issue: https://github.com/sweetrb/apple-mail-mcp/issues/12
     // ───────────────────────────────────────────────────────────────────
     sendEmail(to, subject, body, cc, bcc, account, attachments) {

package/build/services/smtpMailer.d.ts

@@ -0,0 +1,85 @@
+/**
+ * SMTP transport for sending mail (issue #12).
+ *
+ * Mail.app's AppleScript send path wraps any injected body in
+ * `<blockquote type="cite">` under the Apple-Mail-URLShareWrapperClass template
+ * on macOS 15+, so messages render to recipients as quoted/forwarded content
+ * (Apple radar FB11734014, open since Ventura). This module bypasses Mail.app
+ * entirely and submits clean MIME directly over SMTP via nodemailer.
+ *
+ * Connection settings come from environment variables; the password is read
+ * from the macOS Keychain via the `security` CLI by default so no secret is
+ * ever placed in config. AppleScript remains the default transport — SMTP is
+ * opt-in per call (`transport: "smtp"`).
+ *
+ * @module services/smtpMailer
+ */
+import nodemailer from "nodemailer";
+/** Options for an SMTP send, mirroring the AppleScript send-email surface. */
+export interface SmtpSendOptions {
+    to: string[];
+    subject: string;
+    body: string;
+    cc?: string[];
+    bcc?: string[];
+    /** Overrides the configured From address (must be allowed by the SMTP server). */
+    from?: string;
+    /** Absolute paths to files to attach. */
+    attachments?: string[];
+}
+/** Resolved SMTP connection configuration. */
+export interface SmtpConfig {
+    host: string;
+    port: number;
+    secure: boolean;
+    user: string;
+    pass: string;
+    from: string;
+}
+/** Result of an SMTP send. */
+export interface SmtpSendResult {
+    success: boolean;
+    messageId?: string;
+    error?: string;
+}
+/**
+ * Environment variables consumed by {@link resolveSmtpConfig}. Documented here
+ * (and in the README) so the error path can point users at exactly what to set.
+ */
+export declare const SMTP_ENV: {
+    readonly host: "APPLE_MAIL_MCP_SMTP_HOST";
+    readonly port: "APPLE_MAIL_MCP_SMTP_PORT";
+    readonly secure: "APPLE_MAIL_MCP_SMTP_SECURE";
+    readonly user: "APPLE_MAIL_MCP_SMTP_USER";
+    readonly from: "APPLE_MAIL_MCP_SMTP_FROM";
+    readonly password: "APPLE_MAIL_MCP_SMTP_PASSWORD";
+    readonly keychainService: "APPLE_MAIL_MCP_SMTP_KEYCHAIN_SERVICE";
+    readonly keychainAccount: "APPLE_MAIL_MCP_SMTP_KEYCHAIN_ACCOUNT";
+};
+/**
+ * Reads a password from the macOS login Keychain via the `security` CLI.
+ *
+ * Tries `find-internet-password` first (where Mail.app stores account
+ * passwords) and falls back to `find-generic-password`. Returns null if no
+ * matching item exists or the lookup fails for any reason — callers fall back
+ * to the password env var and ultimately surface a clear configuration error.
+ *
+ * @param service - Keychain service / server name (typically the SMTP host)
+ * @param account - Keychain account (typically the SMTP username)
+ */
+export declare function readKeychainPassword(service: string, account: string): string | null;
+/**
+ * Resolves SMTP connection configuration from environment + Keychain.
+ *
+ * @throws Error with an actionable message listing the missing settings.
+ */
+export declare function resolveSmtpConfig(env?: NodeJS.ProcessEnv): SmtpConfig;
+/**
+ * Sends an email over SMTP, producing clean MIME with no blockquote wrapping.
+ *
+ * Config is resolved via {@link resolveSmtpConfig} unless one is injected (the
+ * `config` parameter exists for testing). The body is sent as plain text; pass
+ * a transporter factory only in tests.
+ */
+export declare function sendViaSmtp(opts: SmtpSendOptions, config?: SmtpConfig, createTransport?: typeof nodemailer.createTransport): Promise<SmtpSendResult>;
+//# sourceMappingURL=smtpMailer.d.ts.map

package/build/services/smtpMailer.d.ts.map

@@ -0,0 +1 @@
+{"version":3,"file":"smtpMailer.d.ts","sourceRoot":"","sources":["../../src/services/smtpMailer.ts"],"names":[],"mappings":"AAAA;;;;;;;;;;;;;;;GAeG;AAEH,OAAO,UAAU,MAAM,YAAY,CAAC;AAKpC,8EAA8E;AAC9E,MAAM,WAAW,eAAe;IAC9B,EAAE,EAAE,MAAM,EAAE,CAAC;IACb,OAAO,EAAE,MAAM,CAAC;IAChB,IAAI,EAAE,MAAM,CAAC;IACb,EAAE,CAAC,EAAE,MAAM,EAAE,CAAC;IACd,GAAG,CAAC,EAAE,MAAM,EAAE,CAAC;IACf,kFAAkF;IAClF,IAAI,CAAC,EAAE,MAAM,CAAC;IACd,yCAAyC;IACzC,WAAW,CAAC,EAAE,MAAM,EAAE,CAAC;CACxB;AAED,8CAA8C;AAC9C,MAAM,WAAW,UAAU;IACzB,IAAI,EAAE,MAAM,CAAC;IACb,IAAI,EAAE,MAAM,CAAC;IACb,MAAM,EAAE,OAAO,CAAC;IAChB,IAAI,EAAE,MAAM,CAAC;IACb,IAAI,EAAE,MAAM,CAAC;IACb,IAAI,EAAE,MAAM,CAAC;CACd;AAED,8BAA8B;AAC9B,MAAM,WAAW,cAAc;IAC7B,OAAO,EAAE,OAAO,CAAC;IACjB,SAAS,CAAC,EAAE,MAAM,CAAC;IACnB,KAAK,CAAC,EAAE,MAAM,CAAC;CAChB;AAED;;;GAGG;AACH,eAAO,MAAM,QAAQ;;;;;;;;;CASX,CAAC;AAEX;;;;;;;;;;GAUG;AACH,wBAAgB,oBAAoB,CAAC,OAAO,EAAE,MAAM,EAAE,OAAO,EAAE,MAAM,GAAG,MAAM,GAAG,IAAI,CAcpF;AAED;;;;GAIG;AACH,wBAAgB,iBAAiB,CAAC,GAAG,GAAE,MAAM,CAAC,UAAwB,GAAG,UAAU,CA8ClF;AAmBD;;;;;;GAMG;AACH,wBAAsB,WAAW,CAC/B,IAAI,EAAE,eAAe,EACrB,MAAM,CAAC,EAAE,UAAU,EACnB,eAAe,GAAE,OAAO,UAAU,CAAC,eAA4C,GAC9E,OAAO,CAAC,cAAc,CAAC,CAyCzB"}

package/build/services/smtpMailer.js

@@ -0,0 +1,172 @@
+/**
+ * SMTP transport for sending mail (issue #12).
+ *
+ * Mail.app's AppleScript send path wraps any injected body in
+ * `<blockquote type="cite">` under the Apple-Mail-URLShareWrapperClass template
+ * on macOS 15+, so messages render to recipients as quoted/forwarded content
+ * (Apple radar FB11734014, open since Ventura). This module bypasses Mail.app
+ * entirely and submits clean MIME directly over SMTP via nodemailer.
+ *
+ * Connection settings come from environment variables; the password is read
+ * from the macOS Keychain via the `security` CLI by default so no secret is
+ * ever placed in config. AppleScript remains the default transport — SMTP is
+ * opt-in per call (`transport: "smtp"`).
+ *
+ * @module services/smtpMailer
+ */
+import nodemailer from "nodemailer";
+import { execFileSync } from "child_process";
+import { isAbsolute } from "path";
+import { existsSync } from "fs";
+/**
+ * Environment variables consumed by {@link resolveSmtpConfig}. Documented here
+ * (and in the README) so the error path can point users at exactly what to set.
+ */
+export const SMTP_ENV = {
+    host: "APPLE_MAIL_MCP_SMTP_HOST",
+    port: "APPLE_MAIL_MCP_SMTP_PORT",
+    secure: "APPLE_MAIL_MCP_SMTP_SECURE",
+    user: "APPLE_MAIL_MCP_SMTP_USER",
+    from: "APPLE_MAIL_MCP_SMTP_FROM",
+    password: "APPLE_MAIL_MCP_SMTP_PASSWORD",
+    keychainService: "APPLE_MAIL_MCP_SMTP_KEYCHAIN_SERVICE",
+    keychainAccount: "APPLE_MAIL_MCP_SMTP_KEYCHAIN_ACCOUNT",
+};
+/**
+ * Reads a password from the macOS login Keychain via the `security` CLI.
+ *
+ * Tries `find-internet-password` first (where Mail.app stores account
+ * passwords) and falls back to `find-generic-password`. Returns null if no
+ * matching item exists or the lookup fails for any reason — callers fall back
+ * to the password env var and ultimately surface a clear configuration error.
+ *
+ * @param service - Keychain service / server name (typically the SMTP host)
+ * @param account - Keychain account (typically the SMTP username)
+ */
+export function readKeychainPassword(service, account) {
+    for (const kind of ["find-internet-password", "find-generic-password"]) {
+        try {
+            const out = execFileSync("security", [kind, "-s", service, "-a", account, "-w"], {
+                encoding: "utf8",
+                stdio: ["ignore", "pipe", "ignore"],
+            });
+            const pass = out.replace(/\n$/, "");
+            if (pass)
+                return pass;
+        }
+        catch {
+            // Not found via this kind; try the next.
+        }
+    }
+    return null;
+}
+/**
+ * Resolves SMTP connection configuration from environment + Keychain.
+ *
+ * @throws Error with an actionable message listing the missing settings.
+ */
+export function resolveSmtpConfig(env = process.env) {
+    const host = env[SMTP_ENV.host]?.trim();
+    const user = env[SMTP_ENV.user]?.trim();
+    const missing = [];
+    if (!host)
+        missing.push(SMTP_ENV.host);
+    if (!user)
+        missing.push(SMTP_ENV.user);
+    if (missing.length > 0) {
+        throw new Error(`SMTP transport is not configured. Set ${missing.join(" and ")} ` +
+            `(plus a password via ${SMTP_ENV.password} or the Keychain). ` +
+            `See the README "SMTP transport" section.`);
+    }
+    // secure=true => implicit TLS (port 465); otherwise STARTTLS (port 587).
+    const secure = /^(1|true|yes)$/i.test(env[SMTP_ENV.secure]?.trim() ?? "");
+    const port = env[SMTP_ENV.port]
+        ? Number.parseInt(env[SMTP_ENV.port], 10)
+        : secure
+            ? 465
+            : 587;
+    if (!Number.isInteger(port) || port <= 0) {
+        throw new Error(`Invalid ${SMTP_ENV.port}: "${env[SMTP_ENV.port]}" is not a valid port.`);
+    }
+    const from = env[SMTP_ENV.from]?.trim() || user;
+    // Password: explicit env var wins, otherwise Keychain (service/account
+    // default to the host/user but can be overridden).
+    let pass = env[SMTP_ENV.password];
+    if (!pass) {
+        const service = env[SMTP_ENV.keychainService]?.trim() || host;
+        const account = env[SMTP_ENV.keychainAccount]?.trim() || user;
+        pass = readKeychainPassword(service, account) ?? undefined;
+    }
+    if (!pass) {
+        throw new Error(`No SMTP password found. Set ${SMTP_ENV.password}, or store an internet ` +
+            `password in the Keychain for service "${env[SMTP_ENV.keychainService]?.trim() || host}" / account "${env[SMTP_ENV.keychainAccount]?.trim() || user}".`);
+    }
+    return { host: host, port, secure, user: user, pass, from };
+}
+/**
+ * Validates attachment paths the same way the AppleScript path does: absolute
+ * and existing. Returns nodemailer attachment descriptors.
+ */
+function buildAttachments(attachments) {
+    if (!attachments || attachments.length === 0)
+        return undefined;
+    for (const filePath of attachments) {
+        if (!isAbsolute(filePath)) {
+            throw new Error(`Attachment path must be absolute: "${filePath}"`);
+        }
+        if (!existsSync(filePath)) {
+            throw new Error(`Attachment file not found: "${filePath}"`);
+        }
+    }
+    return attachments.map((path) => ({ path }));
+}
+/**
+ * Sends an email over SMTP, producing clean MIME with no blockquote wrapping.
+ *
+ * Config is resolved via {@link resolveSmtpConfig} unless one is injected (the
+ * `config` parameter exists for testing). The body is sent as plain text; pass
+ * a transporter factory only in tests.
+ */
+export async function sendViaSmtp(opts, config, createTransport = nodemailer.createTransport) {
+    let cfg;
+    try {
+        cfg = config ?? resolveSmtpConfig();
+    }
+    catch (error) {
+        return { success: false, error: error instanceof Error ? error.message : String(error) };
+    }
+    let attachments;
+    try {
+        attachments = buildAttachments(opts.attachments);
+    }
+    catch (error) {
+        return { success: false, error: error instanceof Error ? error.message : String(error) };
+    }
+    const transporter = createTransport({
+        host: cfg.host,
+        port: cfg.port,
+        secure: cfg.secure,
+        auth: { user: cfg.user, pass: cfg.pass },
+    });
+    try {
+        const info = await transporter.sendMail({
+            from: opts.from?.trim() || cfg.from,
+            to: opts.to,
+            cc: opts.cc,
+            bcc: opts.bcc,
+            subject: opts.subject,
+            text: opts.body,
+            attachments,
+        });
+        return { success: true, messageId: info.messageId };
+    }
+    catch (error) {
+        return {
+            success: false,
+            error: `SMTP send failed: ${error instanceof Error ? error.message : String(error)}`,
+        };
+    }
+    finally {
+        transporter.close();
+    }
+}

package/build/utils/applescript.d.ts.map

@@ -1 +1 @@
-{"version":3,"file":"applescript.d.ts","sourceRoot":"","sources":["../../src/utils/applescript.ts"],"names":[],"mappings":"AAAA;;;;;;;GAOG;AAGH,OAAO,KAAK,EAAE,iBAAiB,EAAE,kBAAkB,EAAE,MAAM,YAAY,CAAC;AAuOxE;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;GAiCG;AACH,wBAAgB,kBAAkB,CAChC,MAAM,EAAE,MAAM,EACd,OAAO,GAAE,kBAAuB,GAC/B,iBAAiB,CA6HnB"}
+{"version":3,"file":"applescript.d.ts","sourceRoot":"","sources":["../../src/utils/applescript.ts"],"names":[],"mappings":"AAAA;;;;;;;GAOG;AAGH,OAAO,KAAK,EAAE,iBAAiB,EAAE,kBAAkB,EAAE,MAAM,YAAY,CAAC;AAmQxE;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;GAiCG;AACH,wBAAgB,kBAAkB,CAChC,MAAM,EAAE,MAAM,EACd,OAAO,GAAE,kBAAuB,GAC/B,iBAAiB,CAoInB"}

package/build/utils/applescript.js

@@ -65,6 +65,32 @@ function escapeForShell(script) {
     // This is the standard shell escaping pattern for single-quoted strings
     return script.replace(/'/g, "'\\''");
 }
+/**
+ * Headroom (ms) between the in-AppleScript `with timeout` and the outer
+ * osascript process timeout. The script-level timeout must fire *first* so
+ * Mail.app aborts the operation from inside its own AppleScript dispatch —
+ * cleanly releasing the event queue — before Node SIGKILLs the osascript
+ * process. Killing osascript alone does not stop work already dispatched into
+ * Mail.app, which is what wedges Mail.app for subsequent calls (issue #11).
+ */
+const SCRIPT_TIMEOUT_HEADROOM_MS = 5000;
+/**
+ * Wraps a script body in an AppleScript `with timeout` block so any Apple
+ * Event that honors timeouts (most Mail.app operations do) aborts cleanly
+ * rather than holding Mail.app's single-threaded AppleScript dispatch queue
+ * open indefinitely.
+ *
+ * The timeout is set a few seconds below the osascript process timeout so the
+ * in-Mail abort wins the race against the outer process kill.
+ *
+ * @param script - The AppleScript body
+ * @param processTimeoutMs - The outer osascript process timeout
+ * @returns The script wrapped in `with timeout … end timeout`
+ */
+function wrapWithTimeout(script, processTimeoutMs) {
+    const seconds = Math.max(1, Math.ceil((processTimeoutMs - SCRIPT_TIMEOUT_HEADROOM_MS) / 1000));
+    return `with timeout of ${seconds} seconds\n${script}\nend timeout`;
+}
 /**
  * Checks if an error is a timeout error from execSync.
  *
@@ -270,8 +296,10 @@ export function executeAppleScript(script, options = {}) {
     // Prepare the script:
     // 1. Trim leading/trailing whitespace (cosmetic)
     // 2. Preserve internal newlines (required for AppleScript syntax)
-    // 3. Escape for shell execution
-    const preparedScript = escapeForShell(script.trim());
+    // 3. Wrap in `with timeout` so a stuck Mail.app operation aborts from
+    //    inside its own dispatch before the process timeout kills osascript (#11)
+    // 4. Escape for shell execution
+    const preparedScript = escapeForShell(wrapWithTimeout(script.trim(), timeoutMs));
     // Build the osascript command
     // We use single quotes to wrap the script, which is why we escape
     // single quotes within the script itself
@@ -292,6 +320,11 @@ export function executeAppleScript(script, options = {}) {
             const output = execSync(command, {
                 encoding: "utf8",
                 timeout: timeoutMs,
+                // SIGKILL (not the default SIGTERM): a wedged osascript blocked on an
+                // unresponsive Mail.app can ignore SIGTERM, leaking processes that pile
+                // up and worsen the contention. SIGKILL guarantees the process is reaped
+                // when the timeout fires. (#11)
+                killSignal: "SIGKILL",
                 // Capture stderr separately to get error details
                 stdio: ["pipe", "pipe", "pipe"],
             });

package/build/utils/serialize.d.ts

@@ -0,0 +1,30 @@
+/**
+ * Serial execution gate.
+ *
+ * Mail.app's AppleScript handler is effectively single-threaded: concurrent
+ * `tell application "Mail"` calls queue inside Mail.app, and once enough stack
+ * up the later ones blow past their timeouts while earlier ones are still
+ * draining — the client sees a cascade of "Request timed out" errors and
+ * Mail.app is left half-recovered for the next batch (issue #11).
+ *
+ * A gate chains every task through a single promise so only one runs at a time,
+ * with an optional settle delay between tasks so Mail.app's dispatch queue can
+ * drain. Because tasks are chained on promises, awaiting the gate also yields
+ * the event loop between calls, keeping the server responsive to protocol
+ * traffic (pings, health-check) during a batch.
+ *
+ * @module utils/serialize
+ */
+/** A function that serializes a task behind all previously enqueued tasks. */
+export type SerialGate = <R>(task: () => R | PromiseLike<R>) => Promise<R>;
+/**
+ * Creates a serial execution gate.
+ *
+ * @param settleMs - Delay inserted after each task before the next one starts
+ *   (default 50ms). Set to 0 to disable.
+ * @returns A `serialize(task)` function. Tasks run strictly in enqueue order and
+ *   never overlap; each call resolves/rejects with its task's own result, and a
+ *   failing task never breaks serialization for later tasks.
+ */
+export declare function createSerialGate(settleMs?: number): SerialGate;
+//# sourceMappingURL=serialize.d.ts.map

package/build/utils/serialize.d.ts.map

@@ -0,0 +1 @@
+{"version":3,"file":"serialize.d.ts","sourceRoot":"","sources":["../../src/utils/serialize.ts"],"names":[],"mappings":"AAAA;;;;;;;;;;;;;;;;GAgBG;AAEH,8EAA8E;AAC9E,MAAM,MAAM,UAAU,GAAG,CAAC,CAAC,EAAE,IAAI,EAAE,MAAM,CAAC,GAAG,WAAW,CAAC,CAAC,CAAC,KAAK,OAAO,CAAC,CAAC,CAAC,CAAC;AAE3E;;;;;;;;GAQG;AACH,wBAAgB,gBAAgB,CAAC,QAAQ,SAAK,GAAG,UAAU,CAa1D"}

package/build/utils/serialize.js

@@ -0,0 +1,41 @@
+/**
+ * Serial execution gate.
+ *
+ * Mail.app's AppleScript handler is effectively single-threaded: concurrent
+ * `tell application "Mail"` calls queue inside Mail.app, and once enough stack
+ * up the later ones blow past their timeouts while earlier ones are still
+ * draining — the client sees a cascade of "Request timed out" errors and
+ * Mail.app is left half-recovered for the next batch (issue #11).
+ *
+ * A gate chains every task through a single promise so only one runs at a time,
+ * with an optional settle delay between tasks so Mail.app's dispatch queue can
+ * drain. Because tasks are chained on promises, awaiting the gate also yields
+ * the event loop between calls, keeping the server responsive to protocol
+ * traffic (pings, health-check) during a batch.
+ *
+ * @module utils/serialize
+ */
+/**
+ * Creates a serial execution gate.
+ *
+ * @param settleMs - Delay inserted after each task before the next one starts
+ *   (default 50ms). Set to 0 to disable.
+ * @returns A `serialize(task)` function. Tasks run strictly in enqueue order and
+ *   never overlap; each call resolves/rejects with its task's own result, and a
+ *   failing task never breaks serialization for later tasks.
+ */
+export function createSerialGate(settleMs = 50) {
+    let tail = Promise.resolve();
+    return (task) => {
+        const result = tail.then(task);
+        // Keep the chain alive regardless of this task's outcome, with a settle
+        // delay so the next task doesn't race straight back into Mail.app.
+        tail = result.then(() => settle(settleMs), () => settle(settleMs));
+        return result;
+    };
+}
+function settle(ms) {
+    if (ms <= 0)
+        return Promise.resolve();
+    return new Promise((resolve) => setTimeout(resolve, ms));
+}

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "apple-mail-mcp",
-  "version": "1.5.6",
+  "version": "1.6.0",
   "description": "MCP server for Apple Mail - read, search, send, and manage emails via Claude",
   "type": "module",
   "main": "build/index.js",
@@ -59,10 +59,12 @@
   ],
   "dependencies": {
     "@modelcontextprotocol/sdk": "^1.29.0",
+    "nodemailer": "^9.0.0",
     "zod": "^3.22.4"
   },
   "devDependencies": {
     "@types/node": "^20.0.0",
+    "@types/nodemailer": "^8.0.1",
     "@typescript-eslint/eslint-plugin": "^8.0.0",
     "@typescript-eslint/parser": "^8.0.0",
     "@vitest/coverage-v8": "^4.1.9",