apple-mail-mcp 1.5.7 → 1.6.1

package/README.md

@@ -149,6 +149,27 @@ Search for messages matching criteria. Searches all accounts by default.
 | `dateTo` | string | No | End date filter (e.g., "March 1, 2026") |
 | `limit` | number | No | Max results (default: 50) |
 
+**Large mailboxes & partial results.** Apple Mail's AppleScript bridge cannot
+search very large IMAP/Gmail mailboxes (tens of thousands of messages) before
+the Apple Event times out — empirically even reading the newest 20 messages of
+a 44k-message mailbox takes ~45s. To avoid burning minutes only to return a
+misleading empty result, an unscoped (all-mailboxes) search **skips** mailboxes
+whose message count exceeds a threshold (default **5000**), enforces a
+per-account time budget, and **reports** anything it skipped or that timed out
+rather than silently returning nothing. When coverage is incomplete the result
+includes an explicit warning, e.g.:
+
+```
+⚠️  Partial results — this is NOT a confirmed "no such mail":
+  - skipped mailbox(es) too large to search via AppleScript: Gmail / All Mail (44287) — scope the search with `mailbox` + a `dateFrom`/`dateTo` window to target them
+```
+
+To search inside a large mailbox, scope the call with `mailbox` (and ideally a
+`dateFrom`/`dateTo` window). Tune or disable the skip threshold with the
+`APPLE_MAIL_MAX_SEARCH_MAILBOX` environment variable (default `5000`; set to `0`
+to disable the guard and attempt every mailbox regardless of size).
+([#24](https://github.com/sweetrb/apple-mail-mcp/issues/24))
+
 ---
 
 #### `get-message`
@@ -192,8 +213,9 @@ 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 +228,48 @@ 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`
@@ -735,6 +799,7 @@ The entrypoint is written as:
 | No sending HTML email | Emails are sent as plain text; reading HTML content is supported |
 | Attachments require absolute paths | File attachments must use full absolute paths (e.g., `/Users/me/file.pdf`) |
 | No smart mailboxes | Cannot access Smart Mailboxes via AppleScript |
+| Very large mailboxes not searchable | Apple Mail's AppleScript bridge times out on mailboxes with tens of thousands of messages, so unscoped `search-messages` skips mailboxes above `APPLE_MAIL_MAX_SEARCH_MAILBOX` (default 5000) and reports them as a partial result. Scope with `mailbox` + a date window to search inside one. ([#24](https://github.com/sweetrb/apple-mail-mcp/issues/24)) |
 | In-memory templates | Email templates are not persisted across server restarts |
 | Numeric-only message IDs | Message IDs must contain only digits (validated by schema) |
 | Batch size cap | Batch operations are limited to 100 messages per request |
@@ -742,6 +807,17 @@ 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).
@@ -795,6 +871,12 @@ The `\\\\` in JSON becomes `\\` in the actual string, which represents a single
 - Message IDs change if the message is moved between mailboxes
 - Use `search-messages` to find the current message ID
 
+### `search-messages` says "Partial results" or skips a mailbox
+- This is expected for very large IMAP/Gmail mailboxes (e.g. Gmail's `All Mail`, `Important`): Apple Mail can't scan them via AppleScript before timing out, so they're skipped and named in the result rather than silently returning empty.
+- To search inside one, scope the call with `mailbox` **and** a `dateFrom`/`dateTo` window.
+- Raise or disable the threshold with `APPLE_MAIL_MAX_SEARCH_MAILBOX` (default `5000`; `0` disables the guard) — note that disabling it can make a single search take minutes.
+- A `Partial results` warning means coverage was incomplete; it is **not** a confirmed "no such mail."
+
 ### "Account not found"
 - Account names must match exactly (case-sensitive)
 - Use `list-accounts` to see exact account names

package/build/index.js

@@ -24,6 +24,7 @@ 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
@@ -97,12 +98,14 @@ 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) => {
-        return serializeAppleScript(() => {
+        return serializeAppleScript(async () => {
             try {
-                return handler(params);
+                return await handler(params);
             }
             catch (error) {
                 const message = error instanceof Error ? error.message : "Unknown error";
@@ -133,14 +136,35 @@ server.tool("search-messages", {
     dateTo: DATE_FILTER_SCHEMA.describe("End date filter (e.g., 'March 1, 2026')"),
     limit: z.number().optional().describe("Maximum number of results (default: 50)"),
 }, withErrorHandling(({ query, mailbox, account, limit = 50, dateFrom, dateTo, from, subject, isRead, isFlagged, }) => {
-    const messages = mailManager.searchMessages(query, mailbox, account, limit, dateFrom, dateTo, from, subject, isRead, isFlagged);
+    const { messages, diagnostics } = mailManager.searchMessagesWithDiagnostics(query, mailbox, account, limit, dateFrom, dateTo, from, subject, isRead, isFlagged);
+    // Build a coverage note when the search couldn't reach everything, so a
+    // caller never mistakes an incomplete search for a confirmed "no matches"
+    // (issue #24).
+    const coverageNotes = [];
+    if (diagnostics.timedOutAccounts.length > 0) {
+        coverageNotes.push(`timed out (no results) for account(s): ${diagnostics.timedOutAccounts.join(", ")}`);
+    }
+    if (diagnostics.skippedLargeMailboxes.length > 0) {
+        coverageNotes.push(`skipped mailbox(es) too large to search via AppleScript: ${diagnostics.skippedLargeMailboxes.join(", ")} — scope the search with \`mailbox\` + a \`dateFrom\`/\`dateTo\` window to target them`);
+    }
+    if (diagnostics.notSearchedMailboxes.length > 0) {
+        coverageNotes.push(`could not finish searching mailbox(es): ${diagnostics.notSearchedMailboxes.join(", ")}`);
+    }
+    const coverageBlock = coverageNotes.length > 0
+        ? `\n\n⚠️  Partial results — this is NOT a confirmed "no such mail":\n${coverageNotes
+            .map((n) => `  - ${n}`)
+            .join("\n")}`
+        : "";
     if (messages.length === 0) {
-        return successResponse("No messages found matching criteria");
+        const base = diagnostics.partial
+            ? "No messages found in the portions that were searched."
+            : "No messages found matching criteria";
+        return successResponse(`${base}${coverageBlock}`);
     }
     const messageList = messages
         .map((m) => `  - ID: ${m.id} | ${m.dateReceived.toLocaleDateString()} | ${m.subject} (from: ${m.sender}) [${m.isRead ? "read" : "unread"}]`)
         .join("\n");
-    return successResponse(`Found ${messages.length} message(s):\n${messageList}`);
+    return successResponse(`Found ${messages.length} message(s):\n${messageList}${coverageBlock}`);
 }, "Error searching messages"));
 // --- get-message ---
 server.tool("get-message", {
@@ -190,12 +214,25 @@ 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

@@ -12,7 +12,29 @@
  *
  * @module services/appleMailManager
  */
-import type { Message, MessageContent, Mailbox, Account, Attachment, HealthCheckResult, MailStats, BatchOperationResult, SyncStatus, RecentlyReceivedStats, MailRule, Contact, EmailTemplate, SerialEmailRecipient, SerialEmailResult } from "../types.js";
+import type { Message, MessageContent, Mailbox, Account, Attachment, HealthCheckResult, MailStats, BatchOperationResult, SyncStatus, RecentlyReceivedStats, MailRule, Contact, EmailTemplate, SerialEmailRecipient, SerialEmailResult, SearchDiagnostics, SearchResult } from "../types.js";
+/**
+ * Merge a per-account SearchDiagnostics into an aggregate (all-accounts) one.
+ *
+ * Exported for unit testing.
+ */
+export declare function mergeSearchDiagnostics(into: SearchDiagnostics, from: SearchDiagnostics): void;
+/**
+ * Split a per-account search payload into its message-list portion and parsed
+ * diagnostics. The AppleScript appends a trailer of the form:
+ *
+ *   <messages>|||DIAG|||timedOut=true|||F|||skipped=Foo (9000)|||M||||||F|||notSearched=Bar|||M|||
+ *
+ * `skipped`/`notSearched` are `|||M|||`-separated mailbox names, each prefixed
+ * with the account name on the way out so the aggregate result is unambiguous.
+ *
+ * Exported (pure, no Mail.app dependency) for unit testing — this is the logic
+ * that turns a swallowed timeout into a visible partial result (issue #24).
+ */
+export declare function splitSearchDiagnostics(output: string, account: string): {
+    payload: string;
+    diagnostics: SearchDiagnostics;
+};
 /**
  * Emits AppleScript that builds a date into the variable `varName` from numeric
  * components.
@@ -127,6 +149,30 @@ export declare class AppleMailManager {
      * @returns Array of matching messages
      */
     searchMessages(query?: string, mailbox?: string, account?: string, limit?: number, dateFrom?: string, dateTo?: string, from?: string, subject?: string, isRead?: boolean, isFlagged?: boolean): Message[];
+    /**
+     * Search for messages, returning both the matches and diagnostics describing
+     * how complete the search was.
+     *
+     * This is the correctness fix for issue #24. The previous implementation ran
+     * an unbounded `messages of mb whose <predicate>` over every mailbox in an
+     * account; on large IMAP/Gmail mailboxes (tens of thousands of messages) that
+     * single Apple Event exceeded the timeout, the error was swallowed by a `try`,
+     * and the function returned a clean — but wrong — empty result. Callers/agents
+     * then confidently reported "no such mail."
+     *
+     * Two changes fix that:
+     *  1. Cheap count-guard: mailboxes larger than the scan threshold are skipped
+     *     (Apple Mail can't search them before timing out anyway) and reported.
+     *  2. Honest diagnostics: per-account/per-mailbox timeouts are surfaced as a
+     *     `partial` result with the affected scopes named, instead of an empty
+     *     "success."
+     */
+    searchMessagesWithDiagnostics(query?: string, mailbox?: string, account?: string, limit?: number, dateFrom?: string, dateTo?: string, from?: string, subject?: string, isRead?: boolean, isFlagged?: boolean): SearchResult;
+    /**
+     * Split a per-account search payload into its message list and the DIAG
+     * trailer, parse both, and return a SearchResult. See searchMessagesWithDiagnostics.
+     */
+    private parseSearchResult;
     /**
      * Get a message by ID.
      *

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

@@ -1 +1 @@
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package/build/services/appleMailManager.js

@@ -19,6 +19,94 @@ import { homedir } from "os";
 import { executeAppleScript } from "../utils/applescript.js";
 import { parseMimeAttachments, extractMimeAttachment } from "../utils/mimeParse.js";
 // =============================================================================
+// Search Tuning (issue #24)
+// =============================================================================
+/**
+ * Mailboxes larger than this are skipped during an unscoped (all-mailboxes)
+ * search rather than scanned. Apple Mail's AppleScript bridge cannot search a
+ * mailbox of this size before the Apple Event timeout fires — empirically even
+ * reading the newest 20 messages of a 44k-message Gmail mailbox took ~47s — so
+ * attempting it only burns the time budget and yields a misleading empty
+ * result. `count of messages` is cheap (Mail keeps it cached), so the guard is
+ * effectively free. The skipped mailboxes are reported back to the caller.
+ *
+ * Override with APPLE_MAIL_MAX_SEARCH_MAILBOX (set to 0 to disable the guard).
+ */
+function getMailboxScanThreshold() {
+    const raw = process.env.APPLE_MAIL_MAX_SEARCH_MAILBOX;
+    if (raw !== undefined) {
+        const n = Number(raw);
+        if (Number.isFinite(n) && n >= 0)
+            return n;
+    }
+    return 5000;
+}
+/**
+ * Per-account wall-clock budget (seconds) enforced *inside* the AppleScript so
+ * a single account can't consume minutes. Kept comfortably below the osascript
+ * process timeout (see searchMessages) so the script exits and reports a
+ * partial result rather than being SIGKILLed with no diagnostics.
+ */
+const SEARCH_ACCOUNT_BUDGET_SECONDS = 30;
+/** osascript process timeout for a per-account search (ms). */
+const SEARCH_ACCOUNT_TIMEOUT_MS = 45000;
+/** Separator between the message payload and the diagnostics trailer. */
+const DIAG_MARKER = "|||DIAG|||";
+/**
+ * Merge a per-account SearchDiagnostics into an aggregate (all-accounts) one.
+ *
+ * Exported for unit testing.
+ */
+export function mergeSearchDiagnostics(into, from) {
+    into.timedOutAccounts.push(...from.timedOutAccounts);
+    into.skippedLargeMailboxes.push(...from.skippedLargeMailboxes);
+    into.notSearchedMailboxes.push(...from.notSearchedMailboxes);
+    if (from.partial)
+        into.partial = true;
+}
+/**
+ * Split a per-account search payload into its message-list portion and parsed
+ * diagnostics. The AppleScript appends a trailer of the form:
+ *
+ *   <messages>|||DIAG|||timedOut=true|||F|||skipped=Foo (9000)|||M||||||F|||notSearched=Bar|||M|||
+ *
+ * `skipped`/`notSearched` are `|||M|||`-separated mailbox names, each prefixed
+ * with the account name on the way out so the aggregate result is unambiguous.
+ *
+ * Exported (pure, no Mail.app dependency) for unit testing — this is the logic
+ * that turns a swallowed timeout into a visible partial result (issue #24).
+ */
+export function splitSearchDiagnostics(output, account) {
+    const markerIdx = output.lastIndexOf(DIAG_MARKER);
+    const payload = markerIdx >= 0 ? output.slice(0, markerIdx) : output;
+    const trailer = markerIdx >= 0 ? output.slice(markerIdx + DIAG_MARKER.length) : "";
+    const diagnostics = {
+        partial: false,
+        timedOutAccounts: [],
+        skippedLargeMailboxes: [],
+        notSearchedMailboxes: [],
+    };
+    if (trailer) {
+        const fields = trailer.split("|||F|||");
+        const getField = (key) => {
+            const f = fields.find((x) => x.startsWith(`${key}=`));
+            return f ? f.slice(key.length + 1) : "";
+        };
+        const splitList = (raw) => raw
+            .split("|||M|||")
+            .map((s) => s.trim())
+            .filter((s) => s.length > 0);
+        diagnostics.skippedLargeMailboxes = splitList(getField("skipped")).map((mb) => `${account} / ${mb}`);
+        diagnostics.notSearchedMailboxes = splitList(getField("notSearched")).map((mb) => `${account} / ${mb}`);
+        if (getField("timedOut") === "true")
+            diagnostics.partial = true;
+    }
+    if (diagnostics.skippedLargeMailboxes.length > 0 || diagnostics.notSearchedMailboxes.length > 0) {
+        diagnostics.partial = true;
+    }
+    return { payload, diagnostics };
+}
+// =============================================================================
 // Text Processing Utilities
 // =============================================================================
 /**
@@ -336,18 +424,46 @@ export class AppleMailManager {
      * @returns Array of matching messages
      */
     searchMessages(query, mailbox, account, limit = 50, dateFrom, dateTo, from, subject, isRead, isFlagged) {
-        // If no account specified, search across all accounts
+        return this.searchMessagesWithDiagnostics(query, mailbox, account, limit, dateFrom, dateTo, from, subject, isRead, isFlagged).messages;
+    }
+    /**
+     * Search for messages, returning both the matches and diagnostics describing
+     * how complete the search was.
+     *
+     * This is the correctness fix for issue #24. The previous implementation ran
+     * an unbounded `messages of mb whose <predicate>` over every mailbox in an
+     * account; on large IMAP/Gmail mailboxes (tens of thousands of messages) that
+     * single Apple Event exceeded the timeout, the error was swallowed by a `try`,
+     * and the function returned a clean — but wrong — empty result. Callers/agents
+     * then confidently reported "no such mail."
+     *
+     * Two changes fix that:
+     *  1. Cheap count-guard: mailboxes larger than the scan threshold are skipped
+     *     (Apple Mail can't search them before timing out anyway) and reported.
+     *  2. Honest diagnostics: per-account/per-mailbox timeouts are surfaced as a
+     *     `partial` result with the affected scopes named, instead of an empty
+     *     "success."
+     */
+    searchMessagesWithDiagnostics(query, mailbox, account, limit = 50, dateFrom, dateTo, from, subject, isRead, isFlagged) {
+        // If no account specified, search across all accounts and merge diagnostics.
         if (!account) {
             const accounts = this.listAccounts();
             const allMessages = [];
+            const diagnostics = {
+                partial: false,
+                timedOutAccounts: [],
+                skippedLargeMailboxes: [],
+                notSearchedMailboxes: [],
+            };
             for (const acct of accounts) {
                 if (allMessages.length >= limit)
                     break;
                 const remaining = limit - allMessages.length;
-                const msgs = this.searchMessages(query, mailbox, acct.name, remaining, dateFrom, dateTo, from, subject, isRead, isFlagged);
-                allMessages.push(...msgs);
+                const res = this.searchMessagesWithDiagnostics(query, mailbox, acct.name, remaining, dateFrom, dateTo, from, subject, isRead, isFlagged);
+                allMessages.push(...res.messages);
+                mergeSearchDiagnostics(diagnostics, res.diagnostics);
             }
-            return allMessages.slice(0, limit);
+            return { messages: allMessages.slice(0, limit), diagnostics };
         }
         const targetAccount = this.resolveAccount(account);
         // `query` is a subject-OR-sender substring match; from/subject/isRead/isFlagged
@@ -379,79 +495,136 @@ export class AppleMailManager {
             }
             dateFilter = dateChecks.join(" and ");
         }
+        const scanThreshold = getMailboxScanThreshold();
         let searchCommand;
         if (mailbox) {
-            // Search a specific mailbox
+            // Search a specific mailbox. The caller explicitly chose this mailbox, so
+            // we don't apply the count-guard skip — but we still wrap the scan so a
+            // timeout is reported as a partial result rather than a false empty.
             const targetMailbox = this.resolveMailbox(mailbox, targetAccount);
             searchCommand = `
       ${dateSetup}set outputText to ""
+      set _timedOut to false
+      set _notSearched to ""
       set theMailbox to mailbox "${escapeForAppleScript(targetMailbox)}"
-      set allMessages to messages of theMailbox ${searchCondition}
       set msgCount to 0
-      repeat with msg in allMessages
-        if msgCount >= ${limit} then exit repeat
-        try
-          ${dateFilter ? `set msgDate to date received of msg\n          if not (${dateFilter}) then\n            -- skip message outside date range\n          else` : ""}
-          set msgId to id of msg as string
-          set msgSubject to subject of msg
-          set msgSender to sender of msg
-          set d to date received of msg
-          set msgDateStr to ${AS_DATE_TO_STRING}
-          set msgRead to read status of msg as string
-          set msgFlagged to flagged status of msg as string
-          if msgCount > 0 then set outputText to outputText & "|||ITEM|||"
-          set outputText to outputText & msgId & "|||" & msgSubject & "|||" & msgSender & "|||" & msgDateStr & "|||" & msgRead & "|||" & msgFlagged
-          set msgCount to msgCount + 1
-          ${dateFilter ? "end if" : ""}
-        end try
-      end repeat
-      return outputText
+      try
+        set allMessages to messages of theMailbox ${searchCondition}
+        repeat with msg in allMessages
+          if msgCount >= ${limit} then exit repeat
+          try
+            ${dateFilter ? `set msgDate to date received of msg\n            if not (${dateFilter}) then\n              -- skip message outside date range\n            else` : ""}
+            set msgId to id of msg as string
+            set msgSubject to subject of msg
+            set msgSender to sender of msg
+            set d to date received of msg
+            set msgDateStr to ${AS_DATE_TO_STRING}
+            set msgRead to read status of msg as string
+            set msgFlagged to flagged status of msg as string
+            if msgCount > 0 then set outputText to outputText & "|||ITEM|||"
+            set outputText to outputText & msgId & "|||" & msgSubject & "|||" & msgSender & "|||" & msgDateStr & "|||" & msgRead & "|||" & msgFlagged
+            set msgCount to msgCount + 1
+            ${dateFilter ? "end if" : ""}
+          end try
+        end repeat
+      on error _errMsg number _errNum
+        set _timedOut to true
+        set _notSearched to "${escapeForAppleScript(targetMailbox)}|||M|||"
+      end try
+      return outputText & "${DIAG_MARKER}timedOut=" & (_timedOut as string) & "|||F|||skipped=|||F|||notSearched=" & _notSearched
     `;
         }
         else {
-            // Search ALL mailboxes — iterate every mailbox in the account, dedup by message ID
+            // Search ALL mailboxes — iterate every mailbox in the account, dedup by
+            // message ID. Skip mailboxes that exceed the scan threshold (they can't be
+            // searched before timing out), enforce a per-account wall-clock budget, and
+            // capture per-mailbox timeouts. All three are reported via the DIAG trailer.
+            const scanGuard = scanThreshold > 0 ? `mbCount > ${scanThreshold}` : "false";
             searchCommand = `
       ${dateSetup}set outputText to ""
       set msgCount to 0
       set seenIds to {}
+      set _timedOut to false
+      set _skipped to ""
+      set _notSearched to ""
+      set _startedAt to current date
       repeat with mb in mailboxes
         if msgCount >= ${limit} then exit repeat
+        set mbName to ""
         try
-          set allMessages to messages of mb ${searchCondition}
-          repeat with msg in allMessages
-            if msgCount >= ${limit} then exit repeat
+          set mbName to name of mb
+        end try
+        if ((current date) - _startedAt) > ${SEARCH_ACCOUNT_BUDGET_SECONDS} then
+          set _timedOut to true
+          set _notSearched to _notSearched & mbName & "|||M|||"
+        else
+          set mbCount to 0
+          try
+            set mbCount to count of messages of mb
+          end try
+          if (${scanGuard}) then
+            set _timedOut to true
+            set _skipped to _skipped & mbName & " (" & (mbCount as string) & ")|||M|||"
+          else
             try
-              set msgId to id of msg as string
-              if seenIds does not contain msgId then
-                set end of seenIds to msgId
-                ${dateFilter ? `set msgDate to date received of msg\n                if not (${dateFilter}) then\n                  -- skip message outside date range\n                else` : ""}
-                set msgSubject to subject of msg
-                set msgSender to sender of msg
-                set d to date received of msg
-                set msgDateStr to ${AS_DATE_TO_STRING}
-                set msgRead to read status of msg as string
-                set msgFlagged to flagged status of msg as string
-                if msgCount > 0 then set outputText to outputText & "|||ITEM|||"
-                set outputText to outputText & msgId & "|||" & msgSubject & "|||" & msgSender & "|||" & msgDateStr & "|||" & msgRead & "|||" & msgFlagged & "|||" & name of mb
-                set msgCount to msgCount + 1
-                ${dateFilter ? "end if" : ""}
-              end if
+              set allMessages to messages of mb ${searchCondition}
+              repeat with msg in allMessages
+                if msgCount >= ${limit} then exit repeat
+                try
+                  set msgId to id of msg as string
+                  if seenIds does not contain msgId then
+                    set end of seenIds to msgId
+                    ${dateFilter ? `set msgDate to date received of msg\n                    if not (${dateFilter}) then\n                      -- skip message outside date range\n                    else` : ""}
+                    set msgSubject to subject of msg
+                    set msgSender to sender of msg
+                    set d to date received of msg
+                    set msgDateStr to ${AS_DATE_TO_STRING}
+                    set msgRead to read status of msg as string
+                    set msgFlagged to flagged status of msg as string
+                    if msgCount > 0 then set outputText to outputText & "|||ITEM|||"
+                    set outputText to outputText & msgId & "|||" & msgSubject & "|||" & msgSender & "|||" & msgDateStr & "|||" & msgRead & "|||" & msgFlagged & "|||" & mbName
+                    set msgCount to msgCount + 1
+                    ${dateFilter ? "end if" : ""}
+                  end if
+                end try
+              end repeat
+            on error _errMsg number _errNum
+              set _timedOut to true
+              set _notSearched to _notSearched & mbName & "|||M|||"
             end try
-          end repeat
-        end try
+          end if
+        end if
       end repeat
-      return outputText
+      return outputText & "${DIAG_MARKER}timedOut=" & (_timedOut as string) & "|||F|||skipped=" & _skipped & "|||F|||notSearched=" & _notSearched
     `;
         }
         const script = buildAccountScopedScript(targetAccount, searchCommand);
-        const result = executeAppleScript(script, { timeoutMs: 60000 });
+        const result = executeAppleScript(script, { timeoutMs: SEARCH_ACCOUNT_TIMEOUT_MS });
         if (!result.success) {
-            console.error(`Failed to search messages: ${result.error}`);
-            return [];
+            // Whole-account script failed (most often the osascript process timeout /
+            // SIGKILL on an unresponsive account). Surface it as a timeout rather than
+            // a false empty result — that confusion is the heart of issue #24.
+            console.error(`Failed to search messages in "${targetAccount}": ${result.error}`);
+            return {
+                messages: [],
+                diagnostics: {
+                    partial: true,
+                    timedOutAccounts: [targetAccount],
+                    skippedLargeMailboxes: [],
+                    notSearchedMailboxes: [],
+                },
+            };
         }
-        if (!result.output.trim())
-            return [];
-        return this.parseMessageList(result.output, mailbox || "INBOX", targetAccount);
+        return this.parseSearchResult(result.output, mailbox || "INBOX", targetAccount);
+    }
+    /**
+     * Split a per-account search payload into its message list and the DIAG
+     * trailer, parse both, and return a SearchResult. See searchMessagesWithDiagnostics.
+     */
+    parseSearchResult(output, mailbox, account) {
+        const { payload, diagnostics } = splitSearchDiagnostics(output, account);
+        const messages = payload.trim() ? this.parseMessageList(payload, mailbox, account) : [];
+        return { messages, diagnostics };
     }
     /**
      * Get a message by ID.
@@ -789,13 +962,11 @@ 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/types.d.ts

@@ -47,6 +47,39 @@ export interface Message {
     /** Whether the message has attachments */
     hasAttachments: boolean;
 }
+/**
+ * Per-account / per-mailbox diagnostics for a search, so callers can tell a
+ * genuine "no matches" apart from "we couldn't finish searching."
+ *
+ * Apple Mail's AppleScript bridge is pathologically slow on large IMAP/Gmail
+ * mailboxes (tens of thousands of messages): a single `whose` predicate — or
+ * even reading the newest 20 messages by index — can blow past the Apple Event
+ * timeout. Before this was tracked, those timeouts were swallowed and the
+ * search returned a clean (but wrong) empty result. See issue #24.
+ */
+export interface SearchDiagnostics {
+    /** True if any account/mailbox could not be fully searched (timeout or skip). */
+    partial: boolean;
+    /** Accounts that timed out entirely (whole-account AppleScript was killed). */
+    timedOutAccounts: string[];
+    /**
+     * Mailboxes skipped because their message count exceeded the scan threshold,
+     * formatted as "Account / Mailbox (count)".
+     */
+    skippedLargeMailboxes: string[];
+    /**
+     * Mailboxes that were reached but timed out or errored mid-scan, formatted as
+     * "Account / Mailbox".
+     */
+    notSearchedMailboxes: string[];
+}
+/**
+ * A search result paired with diagnostics about coverage.
+ */
+export interface SearchResult {
+    messages: Message[];
+    diagnostics: SearchDiagnostics;
+}
 /**
  * Represents the content of an email message.
  */

package/build/types.d.ts.map

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package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "apple-mail-mcp",
-  "version": "1.5.7",
+  "version": "1.6.1",
   "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",