apple-mail-mcp 2.4.2 → 2.5.0

package/build/index.js

@@ -26,7 +26,8 @@ import { z } from "zod";
 import { AppleMailManager, isPathWithinAllowedRoots } from "./services/appleMailManager.js";
 import { writeFileSync } from "fs";
 import { resolve as resolvePath, join as joinPath } from "path";
-import { sendViaSmtp, shouldUseSmtp } from "./services/smtpMailer.js";
+import { sendViaSmtp, sendSerialViaSmtp, shouldUseSmtp, isSmtpConfigured, resolveSmtpConfig, } from "./services/smtpMailer.js";
+import { buildReplyOptions, buildForwardOptions, parseOriginalHeaders, } from "./services/replyForward.js";
 import { isImapAccount, resolveImapConfigs, dropAllPools, imapSearchMessages, imapListMessages, imapUnreadCount, imapListMailboxes, imapMailStats, imapListAttachments, imapFetchAttachment, imapBatchMarkRead, imapBatchMarkUnread, imapBatchFlag, imapBatchUnflag, imapBatchDelete, imapBatchMove, imapThread, imapCreateMailbox, imapDeleteMailbox, imapRenameMailbox, imapGetMessage, imapMarkRead, imapMarkUnread, imapFlagMessage, imapUnflagMessage, imapMoveMessageById, imapDeleteMessageById, } from "./services/imapClient.js";
 import { successResponse, errorResponse, partialCoverageBlock, withErrorHandling, messageSummary, } from "./tools/respond.js";
 import { routeMessage } from "./services/messageRouter.js";
@@ -504,8 +505,13 @@ server.registerTool("send-serial-email", {
             .passthrough())
             .optional(),
     },
-}, withErrorHandling(({ recipients, subject, body, account, delayMs }) => {
-    const results = mailManager.sendSerialEmail(recipients, subject, body, account, delayMs);
+}, withErrorHandling(async ({ recipients, subject, body, account, delayMs }) => {
+    // 2.5.0: prefer direct SMTP for mail-merge when configured (and not targeting
+    // a bare Mail.app account label); Mail.app fallback when not configured.
+    const smtpCfg = shouldUseSmtp(undefined, account) ? resolveSmtpOrFallback() : null;
+    const results = smtpCfg
+        ? await sendSerialViaSmtp(recipients, subject, body, smtpCfg, { delayMs })
+        : mailManager.sendSerialEmail(recipients, subject, body, account, delayMs);
     const successCount = results.filter((r) => r.success).length;
     const failCount = results.length - successCount;
     const details = results
@@ -557,6 +563,64 @@ server.registerTool("create-draft", {
         attachmentCount,
     });
 }, "Error creating draft"));
+/** Resolve SMTP config, falling back (host/user set but no password) to Mail.app. */
+function resolveSmtpOrFallback() {
+    try {
+        return resolveSmtpConfig();
+    }
+    catch {
+        return null;
+    }
+}
+/** Reply to a message over direct SMTP with RFC 5322 threading headers. */
+async function sendReplyViaSmtp(id, body, replyAll) {
+    const cfg = resolveSmtpOrFallback();
+    if (!cfg)
+        return { sent: false, fallback: true };
+    const raw = mailManager.getRawSource(id);
+    if (!raw)
+        return { sent: false, fallback: true };
+    const original = parseOriginalHeaders(raw);
+    // Without a Message-ID we can't thread; let Mail.app's reply handle it.
+    if (!original.messageId || original.from.length === 0) {
+        return { sent: false, fallback: true };
+    }
+    const content = mailManager.getMessageContent(id);
+    const opts = buildReplyOptions({
+        original,
+        originalPlainText: content?.plainText ?? "",
+        body,
+        replyAll,
+        self: [cfg.from, cfg.user],
+        from: cfg.from,
+    });
+    const result = await sendViaSmtp(opts, cfg);
+    if (result.success)
+        return { sent: true };
+    return { sent: false, fallback: false, error: result.error ?? "unknown SMTP error" };
+}
+/** Forward a message over direct SMTP (clean MIME, new thread). */
+async function sendForwardViaSmtp(id, to, body) {
+    const cfg = resolveSmtpOrFallback();
+    if (!cfg)
+        return { sent: false, fallback: true };
+    const raw = mailManager.getRawSource(id);
+    if (!raw)
+        return { sent: false, fallback: true };
+    const original = parseOriginalHeaders(raw);
+    const content = mailManager.getMessageContent(id);
+    const opts = buildForwardOptions({
+        original,
+        originalPlainText: content?.plainText ?? "",
+        to,
+        body,
+        from: cfg.from,
+    });
+    const result = await sendViaSmtp(opts, cfg);
+    if (result.success)
+        return { sent: true };
+    return { sent: false, fallback: false, error: result.error ?? "unknown SMTP error" };
+}
 // --- reply-to-message ---
 server.registerTool("reply-to-message", {
     description: "Use when: replying to an existing message by id, preserving its threading headers. Set replyAll for all recipients; set send=false to save as a draft instead of sending.\nReturns: a confirmation that the reply was sent or saved as a draft.\nDo not use when: composing a brand-new message (use send-email / create-draft) or forwarding to new recipients (use forward-message).\nSafety: with the default send=true this SENDS real email immediately and cannot be unsent — require explicit user confirmation of the recipients and body, or pass send=false to let the user review.",
@@ -575,7 +639,19 @@ server.registerTool("reply-to-message", {
         sent: z.boolean().optional(),
         id: z.string().optional(),
     },
-}, withErrorHandling(({ id, body, replyAll, send }) => {
+}, withErrorHandling(async ({ id, body, replyAll, send }) => {
+    // 2.5.0: prefer direct SMTP (clean, correctly threaded MIME) when configured
+    // and actually sending. Drafts (send=false) and the not-configured /
+    // unthreadable cases fall through to the Mail.app AppleScript path.
+    if (send && isSmtpConfigured()) {
+        const outcome = await sendReplyViaSmtp(id, body, replyAll);
+        if (outcome.sent) {
+            return successResponse("Reply sent", { ok: true, sent: true, id });
+        }
+        if (!outcome.fallback) {
+            return errorResponse(`Failed to reply to message "${id}" via SMTP: ${outcome.error}`);
+        }
+    }
     const success = mailManager.replyToMessage(id, body, replyAll, send);
     if (!success) {
         return errorResponse(`Failed to reply to message "${id}"`);
@@ -605,7 +681,22 @@ server.registerTool("forward-message", {
         recipients: z.array(z.string()).optional(),
         id: z.string().optional(),
     },
-}, withErrorHandling(({ id, to, body, send }) => {
+}, withErrorHandling(async ({ id, to, body, send }) => {
+    // 2.5.0: prefer direct SMTP (clean MIME) when configured and actually sending.
+    if (send && isSmtpConfigured()) {
+        const outcome = await sendForwardViaSmtp(id, to, body);
+        if (outcome.sent) {
+            return successResponse(`Message forwarded to ${to.join(", ")}`, {
+                ok: true,
+                sent: true,
+                recipients: to,
+                id,
+            });
+        }
+        if (!outcome.fallback) {
+            return errorResponse(`Failed to forward message "${id}" via SMTP: ${outcome.error}`);
+        }
+    }
     const success = mailManager.forwardMessage(id, to, body, send);
     if (!success) {
         return errorResponse(`Failed to forward message "${id}"`);
@@ -1036,9 +1127,9 @@ server.registerTool("create-mailbox", {
             return errorResponse(r.error || `Failed to create mailbox "${name}"`);
         return successResponse(r.info || `Mailbox "${name}" created`, { ok: true, name });
     }
-    const success = mailManager.createMailbox(name, account);
+    const { success, error } = mailManager.createMailbox(name, account);
     if (!success) {
-        return errorResponse(`Failed to create mailbox "${name}"`);
+        return errorResponse(error || `Failed to create mailbox "${name}"`);
     }
     return successResponse(`Mailbox "${name}" created`, { ok: true, name });
 }, "Error creating mailbox"));

package/build/services/appleMailManager.d.ts

@@ -53,7 +53,7 @@ export declare function isPathWithinAllowedRoots(resolvedPath: string): boolean;
  *
  * Exported for unit testing.
  */
-export declare function describeMailboxOpError(op: "delete" | "rename", raw: string): string;
+export declare function describeMailboxOpError(op: "create" | "delete" | "rename", raw: string): string;
 /** Env var to pin the default account (matched by account name or email). */
 export declare const DEFAULT_ACCOUNT_ENV = "APPLE_MAIL_MCP_DEFAULT_ACCOUNT";
 /**
@@ -153,6 +153,38 @@ export declare class AppleMailManager {
      * mailbox structure (create/delete/rename mailbox).
      */
     private invalidateCache;
+    /**
+     * Reads the live `enabled` flag for an account directly from Mail (bypassing
+     * the 60 s account cache) so a guard reflects an account that was enabled or
+     * disabled out-of-band. Returns true/false when known, or null when the probe
+     * is inconclusive — account not found, or the probe itself failed. Callers
+     * treat null as "can't tell, don't block".
+     */
+    private isAccountEnabled;
+    /**
+     * Guard for AppleScript-backed structural operations (create / delete / rename
+     * mailbox). When the target account is disabled in Mail, Mail holds no live
+     * server session for it, so the operation fails inside Mail with an opaque
+     * AppleEvent -10000 — and a multi-step op like rename can leave half-built
+     * state behind (an orphaned destination mailbox). Detect the disabled account
+     * up front and refuse with an actionable message instead of attempting the
+     * doomed op.
+     *
+     * Returns an error string when the account is known-disabled, else null —
+     * including when the state can't be determined. We fail open: an inconclusive
+     * probe never blocks an otherwise-valid operation.
+     *
+     * Applies only to the AppleScript backend. Direct-IMAP accounts talk to the
+     * server independent of Mail's enabled toggle and are routed before reaching
+     * the manager.
+     */
+    private disabledAccountGuard;
+    /**
+     * Best-effort rollback for a failed rename: delete a just-created destination
+     * mailbox, but ONLY if it is empty, so any messages that did move are never
+     * destroyed. Returns true if the empty orphan was removed.
+     */
+    private deleteMailboxIfEmpty;
     /**
      * Resolves the account to use for an operation when the caller omits one.
      *
@@ -479,7 +511,10 @@ export declare class AppleMailManager {
     /**
      * Create a new mailbox.
      */
-    createMailbox(name: string, account?: string): boolean;
+    createMailbox(name: string, account?: string): {
+        success: boolean;
+        error?: string;
+    };
     /**
      * Delete a mailbox.
      */

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

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+{"version":3,"file":"appleMailManager.d.ts","sourceRoot":"","sources":["../../src/services/appleMailManager.ts"],"names":[],"mappings":"AAAA;;;;;;;;;;;;;GAaG;AAUH,OAAO,KAAK,EACV,OAAO,EACP,cAAc,EACd,OAAO,EACP,OAAO,EACP,UAAU,EACV,iBAAiB,EACjB,SAAS,EAET,oBAAoB,EACpB,UAAU,EACV,qBAAqB,EACrB,QAAQ,EACR,QAAQ,EAGR,eAAe,EACf,OAAO,EACP,aAAa,EACb,oBAAoB,EACpB,iBAAiB,EACjB,iBAAiB,EACjB,YAAY,EACb,MAAM,YAAY,CAAC;AA2DpB;;;;GAIG;AACH,wBAAgB,sBAAsB,CAAC,IAAI,EAAE,iBAAiB,EAAE,IAAI,EAAE,iBAAiB,GAAG,IAAI,CAK7F;AAED;;;;;;;;;;;;GAYG;AACH,wBAAgB,sBAAsB,CACpC,MAAM,EAAE,MAAM,EACd,OAAO,EAAE,MAAM,GACd;IAAE,OAAO,EAAE,MAAM,CAAC;IAAC,WAAW,EAAE,iBAAiB,CAAA;CAAE,CAsCrD;AAqBD;;;;;;;;GAQG;AACH,wBAAgB,wBAAwB,CAAC,YAAY,EAAE,MAAM,GAAG,OAAO,CAKtE;AAWD;;;;;;GAMG;AACH,wBAAgB,sBAAsB,CAAC,EAAE,EAAE,QAAQ,GAAG,QAAQ,GAAG,QAAQ,EAAE,GAAG,EAAE,MAAM,GAAG,MAAM,CAO9F;AAED,6EAA6E;AAC7E,eAAO,MAAM,mBAAmB,mCAAmC,CAAC;AAEpE;;;;;;;;;;;;GAYG;AACH,wBAAgB,oBAAoB,CAClC,QAAQ,EAAE,OAAO,EAAE,EACnB,IAAI,GAAE;IAAE,QAAQ,CAAC,EAAE,MAAM,CAAC;IAAC,gBAAgB,CAAC,EAAE,MAAM,CAAA;CAAO,GAC1D,MAAM,GAAG,IAAI,CAgBf;AAED,wBAAgB,oBAAoB,CAAC,IAAI,EAAE,MAAM,GAAG,MAAM,CAczD;AAwKD;;;;;;;;;;;;;;;GAeG;AACH,wBAAgB,oBAAoB,CAAC,OAAO,EAAE,MAAM,EAAE,CAAC,EAAE,IAAI,GAAG,MAAM,CAWrE;AA2CD;;;;;;;;;;;;GAYG;AACH,MAAM,WAAW,sBAAsB;IACrC,KAAK,CAAC,EAAE,MAAM,CAAC;IACf,IAAI,CAAC,EAAE,MAAM,CAAC;IACd,OAAO,CAAC,EAAE,MAAM,CAAC;IACjB,MAAM,CAAC,EAAE,OAAO,CAAC;IACjB,SAAS,CAAC,EAAE,OAAO,CAAC;CACrB;AAED;;;;;;;;;;;;GAYG;AACH,wBAAgB,oBAAoB,CAAC,OAAO,EAAE,sBAAsB,GAAG,MAAM,CAoB5E;AAED,qBAAa,gBAAgB;IAC3B;;OAEG;IACH,OAAO,CAAC,cAAc,CAAuB;IAE7C;;;;OAIG;IACH,OAAO,CAAC,KAAK,CAGX;IAEF,8CAA8C;IAC9C,OAAO,CAAC,QAAQ,CAAC,YAAY,CAAU;IAEvC;;OAEG;IACH,OAAO,CAAC,iBAAiB;IAUzB;;;;OAIG;IACH,OAAO,CAAC,qBAAqB;IAW7B;;;OAGG;IACH,OAAO,CAAC,eAAe;IAKvB;;;;;;OAMG;IACH,OAAO,CAAC,gBAAgB;IAkBxB;;;;;;;;;;;;;;;;OAgBG;IACH,OAAO,CAAC,oBAAoB;IAO5B;;;;OAIG;IACH,OAAO,CAAC,oBAAoB;IAqB5B;;;;;;OAMG;IACH,OAAO,CAAC,cAAc;IAqCtB;;;;;;;;;;;;;;;;;OAiBG;IACH,OAAO,CAAC,cAAc;IAyCtB;;;;;;;;OAQG;IACH,cAAc,CACZ,KAAK,CAAC,EAAE,MAAM,EACd,OAAO,CAAC,EAAE,MAAM,EAChB,OAAO,CAAC,EAAE,MAAM,EAChB,KAAK,SAAK,EACV,QAAQ,CAAC,EAAE,MAAM,EACjB,MAAM,CAAC,EAAE,MAAM,EACf,IAAI,CAAC,EAAE,MAAM,EACb,OAAO,CAAC,EAAE,MAAM,EAChB,MAAM,CAAC,EAAE,OAAO,EAChB,SAAS,CAAC,EAAE,OAAO,GAClB,OAAO,EAAE;IAeZ;;;;;;;;;;;;;;;;;OAiBG;IACH,6BAA6B,CAC3B,KAAK,CAAC,EAAE,MAAM,EACd,OAAO,CAAC,EAAE,MAAM,EAChB,OAAO,CAAC,EAAE,MAAM,EAChB,KAAK,SAAK,EACV,QAAQ,CAAC,EAAE,MAAM,EACjB,MAAM,CAAC,EAAE,MAAM,EACf,IAAI,CAAC,EAAE,MAAM,EACb,OAAO,CAAC,EAAE,MAAM,EAChB,MAAM,CAAC,EAAE,OAAO,EAChB,SAAS,CAAC,EAAE,OAAO,GAClB,YAAY;IA2Jf;;;OAGG;IACH,OAAO,CAAC,iBAAiB;IAMzB;;;;;OAKG;IACH,cAAc,CAAC,EAAE,EAAE,MAAM,EAAE,mBAAmB,UAAQ,GAAG,OAAO,GAAG,IAAI;IA4EvE;;;;;;;;;OASG;IACH,iBAAiB,CAAC,EAAE,EAAE,MAAM,EAAE,WAAW,UAAQ,GAAG,cAAc,GAAG,IAAI;IAyDzE;;;;;;;;OAQG;IACH,YAAY,CAAC,EAAE,EAAE,MAAM,GAAG,MAAM,GAAG,IAAI;IA6BvC;;;;;;;OAOG;IACH,YAAY,CACV,OAAO,CAAC,EAAE,MAAM,EAChB,OAAO,CAAC,EAAE,MAAM,EAChB,KAAK,SAAK,EACV,IAAI,CAAC,EAAE,MAAM,EACb,MAAM,SAAI,GACT,OAAO,EAAE;IAIZ;;;;;;;;;;;OAWG;IACH,2BAA2B,CACzB,OAAO,CAAC,EAAE,MAAM,EAChB,OAAO,CAAC,EAAE,MAAM,EAChB,KAAK,SAAK,EACV,IAAI,CAAC,EAAE,MAAM,EACb,MAAM,SAAI,GACT,YAAY;IAiHf;;;;;;;;;;OAUG;IACH,OAAO,CAAC,gBAAgB;IAoCxB;;;;;;;;;;OAUG;IAuBH,SAAS,CACP,EAAE,EAAE,MAAM,EAAE,EACZ,OAAO,EAAE,MAAM,EACf,IAAI,EAAE,MAAM,EACZ,EAAE,CAAC,EAAE,MAAM,EAAE,EACb,GAAG,CAAC,EAAE,MAAM,EAAE,EACd,OAAO,CAAC,EAAE,MAAM,EAChB,WAAW,CAAC,EAAE,eAAe,EAAE,GAC9B,OAAO;IAoCV,OAAO,CAAC,kBAAkB;IA2C1B;;;;;;;;;;;;OAYG;IACH,eAAe,CACb,UAAU,EAAE,oBAAoB,EAAE,EAClC,OAAO,EAAE,MAAM,EACf,IAAI,EAAE,MAAM,EACZ,OAAO,CAAC,EAAE,MAAM,EAChB,OAAO,GAAE,MAAY,GACpB,iBAAiB,EAAE;IAgDtB;;;;;;;;;;OAUG;IACH,WAAW,CACT,EAAE,EAAE,MAAM,EAAE,EACZ,OAAO,EAAE,MAAM,EACf,IAAI,EAAE,MAAM,EACZ,EAAE,CAAC,EAAE,MAAM,EAAE,EACb,GAAG,CAAC,EAAE,MAAM,EAAE,EACd,OAAO,CAAC,EAAE,MAAM,EAChB,WAAW,CAAC,EAAE,eAAe,EAAE,GAC9B,OAAO;IAoCV,OAAO,CAAC,uBAAuB;IAyC/B;;;;;;;;OAQG;IACH,cAAc,CAAC,EAAE,EAAE,MAAM,EAAE,IAAI,EAAE,MAAM,EAAE,QAAQ,UAAQ,EAAE,IAAI,UAAO,GAAG,OAAO;IAqChF;;;;;;;;OAQG;IACH,cAAc,CAAC,EAAE,EAAE,MAAM,EAAE,EAAE,EAAE,MAAM,EAAE,EAAE,IAAI,CAAC,EAAE,MAAM,EAAE,IAAI,UAAO,GAAG,OAAO;IA2C7E;;OAEG;IACH,OAAO,CAAC,iBAAiB;IAsBzB;;OAEG;IACH,UAAU,CAAC,EAAE,EAAE,MAAM,GAAG,OAAO;IAY/B;;OAEG;IACH,YAAY,CAAC,EAAE,EAAE,MAAM,GAAG,OAAO;IAYjC;;OAEG;IACH,WAAW,CAAC,EAAE,EAAE,MAAM,GAAG,OAAO;IAYhC;;OAEG;IACH,aAAa,CAAC,EAAE,EAAE,MAAM,GAAG,OAAO;IAYlC;;OAEG;IACH,aAAa,CAAC,EAAE,EAAE,MAAM,GAAG;QAAE,OAAO,EAAE,OAAO,CAAC;QAAC,KAAK,CAAC,EAAE,MAAM,CAAA;KAAE;IAgB/D;;;;;;;;;OASG;IACH,OAAO,CAAC,4BAA4B;IAkBpC;;OAEG;IACH;;;;;;;;;;;;;;;;;OAiBG;IACH,OAAO,CAAC,mBAAmB;IAwD3B,WAAW,CAAC,EAAE,EAAE,MAAM,EAAE,OAAO,EAAE,MAAM,EAAE,OAAO,CAAC,EAAE,MAAM,GAAG;QAAE,OAAO,EAAE,OAAO,CAAC;QAAC,KAAK,CAAC,EAAE,MAAM,CAAA;KAAE;IAgBhG;;;;;;;;;;;;;;;OAeG;IACH,OAAO,CAAC,iBAAiB;IAoGzB;;OAEG;IACH,mBAAmB,CAAC,GAAG,EAAE,MAAM,EAAE,GAAG,oBAAoB,EAAE;IAI1D;;;;;;OAMG;IACH,iBAAiB,CAAC,GAAG,EAAE,MAAM,EAAE,EAAE,OAAO,EAAE,MAAM,EAAE,OAAO,CAAC,EAAE,MAAM,GAAG,oBAAoB,EAAE;IAsB3F;;OAEG;IACH,eAAe,CAAC,GAAG,EAAE,MAAM,EAAE,GAAG,oBAAoB,EAAE;IAItD;;OAEG;IACH,iBAAiB,CAAC,GAAG,EAAE,MAAM,EAAE,GAAG,oBAAoB,EAAE;IAIx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package/build/services/appleMailManager.js

@@ -178,7 +178,7 @@ const UNSUPPORTED_APPLESCRIPT_OP = /AppleEvent handler failed|-10000/i;
 export function describeMailboxOpError(op, raw) {
     const trimmed = (raw || "").trim();
     if (UNSUPPORTED_APPLESCRIPT_OP.test(trimmed)) {
-        const verb = op === "delete" ? "Delete" : "Rename";
+        const verb = op.charAt(0).toUpperCase() + op.slice(1);
         return `Mail.app cannot ${op} server-side (IMAP / Gmail / Workspace / iCloud / Exchange) mailboxes via AppleScript — only local "On My Mac" mailboxes support this. ${verb} it in Mail.app directly. (Mail.app error: ${trimmed})`;
     }
     return trimmed || `Failed to ${op} mailbox`;
@@ -523,6 +523,77 @@ export class AppleMailManager {
         this.cache.accounts = null;
         this.cache.mailboxNames.clear();
     }
+    /**
+     * Reads the live `enabled` flag for an account directly from Mail (bypassing
+     * the 60 s account cache) so a guard reflects an account that was enabled or
+     * disabled out-of-band. Returns true/false when known, or null when the probe
+     * is inconclusive — account not found, or the probe itself failed. Callers
+     * treat null as "can't tell, don't block".
+     */
+    isAccountEnabled(account) {
+        const safeAccount = escapeForAppleScript(account);
+        const result = executeAppleScript(buildAppLevelScript(`
+        try
+          return (enabled of account "${safeAccount}") as text
+        on error
+          return "missing"
+        end try
+      `));
+        if (!result.success)
+            return null;
+        const out = result.output.trim();
+        if (out === "true")
+            return true;
+        if (out === "false")
+            return false;
+        return null;
+    }
+    /**
+     * Guard for AppleScript-backed structural operations (create / delete / rename
+     * mailbox). When the target account is disabled in Mail, Mail holds no live
+     * server session for it, so the operation fails inside Mail with an opaque
+     * AppleEvent -10000 — and a multi-step op like rename can leave half-built
+     * state behind (an orphaned destination mailbox). Detect the disabled account
+     * up front and refuse with an actionable message instead of attempting the
+     * doomed op.
+     *
+     * Returns an error string when the account is known-disabled, else null —
+     * including when the state can't be determined. We fail open: an inconclusive
+     * probe never blocks an otherwise-valid operation.
+     *
+     * Applies only to the AppleScript backend. Direct-IMAP accounts talk to the
+     * server independent of Mail's enabled toggle and are routed before reaching
+     * the manager.
+     */
+    disabledAccountGuard(account) {
+        if (this.isAccountEnabled(account) === false) {
+            return `Account "${account}" is disabled in Mail, so Mail has no live connection to it — this operation would fail server-side (AppleEvent -10000) and could leave a mailbox half-changed. Enable the account (Mail ▸ Settings ▸ Accounts ▸ "Enable this account") and retry, or target an enabled account.`;
+        }
+        return null;
+    }
+    /**
+     * Best-effort rollback for a failed rename: delete a just-created destination
+     * mailbox, but ONLY if it is empty, so any messages that did move are never
+     * destroyed. Returns true if the empty orphan was removed.
+     */
+    deleteMailboxIfEmpty(name, account) {
+        const safeName = escapeForAppleScript(name);
+        const safeAccount = escapeForAppleScript(account);
+        const result = executeAppleScript(buildAppLevelScript(`
+        try
+          set mb to mailbox "${safeName}" of account "${safeAccount}"
+          if (count of messages of mb) is 0 then
+            delete mb
+            return "deleted"
+          else
+            return "kept"
+          end if
+        on error errMsg
+          return "error:" & errMsg
+        end try
+      `));
+        return result.success && result.output.trim() === "deleted";
+    }
     /**
      * Resolves the account to use for an operation when the caller omits one.
      *
@@ -2050,6 +2121,11 @@ export class AppleMailManager {
      */
     createMailbox(name, account) {
         const targetAccount = this.resolveAccount(account);
+        const disabled = this.disabledAccountGuard(targetAccount);
+        if (disabled) {
+            console.error(`Refusing to create mailbox: ${disabled}`);
+            return { success: false, error: disabled };
+        }
         const safeName = escapeForAppleScript(name);
         const safeAccount = escapeForAppleScript(targetAccount);
         const script = buildAppLevelScript(`
@@ -2062,17 +2138,26 @@ export class AppleMailManager {
     `);
         const result = executeAppleScript(script);
         if (!result.success || result.output.startsWith("error:")) {
-            console.error(`Failed to create mailbox: ${result.error || result.output}`);
-            return false;
+            const raw = result.success
+                ? result.output.replace(/^error:/, "")
+                : result.error || "Unknown error";
+            const error = describeMailboxOpError("create", raw);
+            console.error(`Failed to create mailbox: ${error}`);
+            return { success: false, error };
         }
         this.invalidateCache();
-        return true;
+        return { success: true };
     }
     /**
      * Delete a mailbox.
      */
     deleteMailbox(name, account) {
         const targetAccount = this.resolveAccount(account);
+        const disabled = this.disabledAccountGuard(targetAccount);
+        if (disabled) {
+            console.error(`Refusing to delete mailbox: ${disabled}`);
+            return { success: false, error: disabled };
+        }
         const targetMailbox = this.resolveMailbox(name, targetAccount);
         const safeName = escapeForAppleScript(targetMailbox);
         const safeAccount = escapeForAppleScript(targetAccount);
@@ -2101,11 +2186,15 @@ export class AppleMailManager {
      */
     renameMailbox(oldName, newName, account) {
         const targetAccount = this.resolveAccount(account);
-        // Create the new mailbox
-        if (!this.createMailbox(newName, targetAccount)) {
+        // Create the new mailbox. createMailbox runs the disabled-account guard, so
+        // a disabled target is refused here before anything is built — no orphan can
+        // be created. Propagate its (more specific) error rather than a generic one.
+        const created = this.createMailbox(newName, targetAccount);
+        if (!created.success) {
             return {
                 success: false,
-                error: `Could not create the destination mailbox "${newName}" needed for the rename.`,
+                error: created.error ??
+                    `Could not create the destination mailbox "${newName}" needed for the rename.`,
             };
         }
         // Move all messages from old to new
@@ -2155,9 +2244,16 @@ export class AppleMailManager {
             const raw = result.success
                 ? result.output.replace(/^error:/, "")
                 : result.error || "Unknown error";
-            // The empty destination mailbox we just created is now an orphan; the
-            // source is untouched (delete only runs after a verified-empty move).
-            const error = describeMailboxOpError("rename", raw);
+            // Roll back the destination we just created so a failed rename doesn't
+            // leave an orphan (as a partial-failure once did — the _amcp_rename_test_*
+            // ghosts). deleteMailboxIfEmpty only removes it when empty, so any
+            // messages that did move are never destroyed; the source is untouched
+            // (its delete only runs after a verified-empty move).
+            const rolledBack = this.deleteMailboxIfEmpty(resolvedNew, targetAccount);
+            let error = describeMailboxOpError("rename", raw);
+            error += rolledBack
+                ? ` The empty destination mailbox "${resolvedNew}" was rolled back, so no orphan was left.`
+                : ` The destination mailbox "${resolvedNew}" was created and could not be auto-removed; delete it manually if it is an empty leftover.`;
             console.error(`Failed to rename mailbox: ${error}`);
             this.invalidateCache();
             return { success: false, error };

package/build/services/imapClient.js

@@ -851,7 +851,7 @@ async function imapBatch(ids, deps, op) {
             errors.push(`Not an IMAP id: "${id}"`);
             continue;
         }
-        const key = `${ref.account}${ref.path}`;
+        const key = `${ref.account}\0${ref.path}`;
         const g = groups.get(key) ?? { account: ref.account, path: ref.path, uids: [] };
         g.uids.push(ref.uid);
         groups.set(key, g);

package/build/services/replyForward.d.ts

@@ -0,0 +1,87 @@
+/**
+ * Pure helpers that turn an existing message (its raw RFC 5322 source plus the
+ * decoded plain-text body) into {@link SmtpSendOptions} for a **threaded reply**
+ * or a **forward** sent over SMTP.
+ *
+ * This is the 2.5.0 "prefer-direct" path: when SMTP is configured we send
+ * replies/forwards ourselves with correct `In-Reply-To`/`References` headers and
+ * a clean MIME body, instead of driving Mail.app's `reply`/`forward` AppleScript
+ * commands (which thread correctly but wrap the injected body in a `blockquote`
+ * on macOS 15+). Kept separate from {@link sendViaSmtp} so the addressing,
+ * subject-prefix, and quoting rules are unit-testable without a live SMTP server.
+ */
+import type { SmtpSendOptions } from "../services/smtpMailer.js";
+/** The subset of an original message's headers we need to reply/forward. */
+export interface OriginalHeaders {
+    /** Raw `Message-ID` including angle brackets, e.g. `<abc@host>`. */
+    messageId?: string;
+    /** Thread chain: every `<id>` from `References` + `In-Reply-To`, in order. */
+    references: string[];
+    /** `From` address(es), bare (no display name). */
+    from: string[];
+    /** `Reply-To` address(es), bare. Preferred over {@link from} for replies. */
+    replyTo: string[];
+    /** `To` address(es), bare. */
+    to: string[];
+    /** `Cc` address(es), bare. */
+    cc: string[];
+    /** `Subject`, unfolded and trimmed (no `Re:`/`Fwd:` normalization). */
+    subject: string;
+    /** `Date` header verbatim, for the reply attribution line. */
+    date?: string;
+}
+/**
+ * Pull bare email addresses out of a header value such as
+ * `"Alice <a@x.com>, bob@y.com"` → `["a@x.com", "bob@y.com"]`. Splits on commas
+ * (address lists are comma-separated) and unwraps `<...>` when present. Anything
+ * without an `@` is dropped, so group syntax / junk is ignored.
+ */
+export declare function extractAddresses(headerValue: string): string[];
+/**
+ * Parse the header block (everything before the first blank line) of a raw
+ * message. Continuation lines (folded headers, leading WSP) are unfolded, and
+ * header names are matched case-insensitively. Only the headers in
+ * {@link OriginalHeaders} are extracted.
+ */
+export declare function parseOriginalHeaders(raw: string): OriginalHeaders;
+/**
+ * Ensure `subject` carries `prefix` exactly once. Existing `Re:`/`Fwd:`/`Fw:`
+ * prefixes (any case) are treated as already-present so we never stack them.
+ */
+export declare function withSubjectPrefix(subject: string, prefix: "Re:" | "Fwd:"): string;
+/** Prefix every line of the original body with `> ` for the quoted reply block. */
+export declare function quoteBody(plainText: string): string;
+/**
+ * Build {@link SmtpSendOptions} for a threaded reply.
+ *
+ * - recipients: `Reply-To` if the original had one, else `From`; with
+ *   `replyAll`, the original `To`+`Cc` (minus our own addresses and the primary
+ *   recipients) become `Cc`.
+ * - subject: `Re: ` prepended unless already present.
+ * - threading: `In-Reply-To` = original `Message-ID`; `References` = original
+ *   chain + that `Message-ID`.
+ * - body: the new text, then an attribution line and the quoted original.
+ */
+export declare function buildReplyOptions(args: {
+    original: OriginalHeaders;
+    originalPlainText: string;
+    body: string;
+    replyAll: boolean;
+    /** Our own addresses, excluded from a reply-all recipient set. */
+    self: string[];
+    /** From override (defaults to the SMTP identity at send time when omitted). */
+    from?: string;
+}): SmtpSendOptions;
+/**
+ * Build {@link SmtpSendOptions} for a forward to new recipients. A forward
+ * starts a new thread, so no `In-Reply-To`/`References` are set — the win over
+ * the AppleScript path is a clean, un-wrapped MIME body.
+ */
+export declare function buildForwardOptions(args: {
+    original: OriginalHeaders;
+    originalPlainText: string;
+    to: string[];
+    body?: string;
+    from?: string;
+}): SmtpSendOptions;
+//# sourceMappingURL=replyForward.d.ts.map

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

@@ -0,0 +1 @@
+{"version":3,"file":"replyForward.d.ts","sourceRoot":"","sources":["../../src/services/replyForward.ts"],"names":[],"mappings":"AAAA;;;;;;;;;;;GAWG;AACH,OAAO,KAAK,EAAE,eAAe,EAAE,MAAM,0BAA0B,CAAC;AAEhE,4EAA4E;AAC5E,MAAM,WAAW,eAAe;IAC9B,oEAAoE;IACpE,SAAS,CAAC,EAAE,MAAM,CAAC;IACnB,8EAA8E;IAC9E,UAAU,EAAE,MAAM,EAAE,CAAC;IACrB,kDAAkD;IAClD,IAAI,EAAE,MAAM,EAAE,CAAC;IACf,6EAA6E;IAC7E,OAAO,EAAE,MAAM,EAAE,CAAC;IAClB,8BAA8B;IAC9B,EAAE,EAAE,MAAM,EAAE,CAAC;IACb,8BAA8B;IAC9B,EAAE,EAAE,MAAM,EAAE,CAAC;IACb,uEAAuE;IACvE,OAAO,EAAE,MAAM,CAAC;IAChB,8DAA8D;IAC9D,IAAI,CAAC,EAAE,MAAM,CAAC;CACf;AAED;;;;;GAKG;AACH,wBAAgB,gBAAgB,CAAC,WAAW,EAAE,MAAM,GAAG,MAAM,EAAE,CAS9D;AAED;;;;;GAKG;AACH,wBAAgB,oBAAoB,CAAC,GAAG,EAAE,MAAM,GAAG,eAAe,CAkCjE;AAgBD;;;GAGG;AACH,wBAAgB,iBAAiB,CAAC,OAAO,EAAE,MAAM,EAAE,MAAM,EAAE,KAAK,GAAG,MAAM,GAAG,MAAM,CAIjF;AAED,mFAAmF;AACnF,wBAAgB,SAAS,CAAC,SAAS,EAAE,MAAM,GAAG,MAAM,CAMnD;AAED;;;;;;;;;;GAUG;AACH,wBAAgB,iBAAiB,CAAC,IAAI,EAAE;IACtC,QAAQ,EAAE,eAAe,CAAC;IAC1B,iBAAiB,EAAE,MAAM,CAAC;IAC1B,IAAI,EAAE,MAAM,CAAC;IACb,QAAQ,EAAE,OAAO,CAAC;IAClB,kEAAkE;IAClE,IAAI,EAAE,MAAM,EAAE,CAAC;IACf,+EAA+E;IAC/E,IAAI,CAAC,EAAE,MAAM,CAAC;CACf,GAAG,eAAe,CAmClB;AAQD;;;;GAIG;AACH,wBAAgB,mBAAmB,CAAC,IAAI,EAAE;IACxC,QAAQ,EAAE,eAAe,CAAC;IAC1B,iBAAiB,EAAE,MAAM,CAAC;IAC1B,EAAE,EAAE,MAAM,EAAE,CAAC;IACb,IAAI,CAAC,EAAE,MAAM,CAAC;IACd,IAAI,CAAC,EAAE,MAAM,CAAC;CACf,GAAG,eAAe,CAsBlB"}

package/build/services/replyForward.js

@@ -0,0 +1,150 @@
+/**
+ * Pull bare email addresses out of a header value such as
+ * `"Alice <a@x.com>, bob@y.com"` → `["a@x.com", "bob@y.com"]`. Splits on commas
+ * (address lists are comma-separated) and unwraps `<...>` when present. Anything
+ * without an `@` is dropped, so group syntax / junk is ignored.
+ */
+export function extractAddresses(headerValue) {
+    if (!headerValue.trim())
+        return [];
+    return headerValue
+        .split(",")
+        .map((part) => {
+        const angle = part.match(/<([^>]+)>/);
+        return (angle ? angle[1] : part).trim();
+    })
+        .filter((addr) => addr.includes("@"));
+}
+/**
+ * Parse the header block (everything before the first blank line) of a raw
+ * message. Continuation lines (folded headers, leading WSP) are unfolded, and
+ * header names are matched case-insensitively. Only the headers in
+ * {@link OriginalHeaders} are extracted.
+ */
+export function parseOriginalHeaders(raw) {
+    const headerBlock = raw.split(/\r?\n\r?\n/)[0] ?? "";
+    // Unfold: any line starting with a space/tab continues the previous header.
+    const lines = [];
+    for (const line of headerBlock.split(/\r?\n/)) {
+        if (/^[ \t]/.test(line) && lines.length > 0) {
+            lines[lines.length - 1] += " " + line.trim();
+        }
+        else {
+            lines.push(line);
+        }
+    }
+    const get = (name) => {
+        const prefix = `${name.toLowerCase()}:`;
+        const found = lines.find((l) => l.toLowerCase().startsWith(prefix));
+        return found ? found.slice(found.indexOf(":") + 1).trim() : undefined;
+    };
+    const rawMessageId = get("Message-ID");
+    const messageId = rawMessageId?.match(/<[^>]+>/)?.[0] ?? rawMessageId ?? undefined;
+    const references = `${get("References") ?? ""} ${get("In-Reply-To") ?? ""}`.match(/<[^>]+>/g) ?? [];
+    return {
+        messageId,
+        references,
+        from: extractAddresses(get("From") ?? ""),
+        replyTo: extractAddresses(get("Reply-To") ?? ""),
+        to: extractAddresses(get("To") ?? ""),
+        cc: extractAddresses(get("Cc") ?? ""),
+        subject: get("Subject") ?? "",
+        date: get("Date"),
+    };
+}
+/** Case-insensitive de-dupe that preserves first-seen order and casing. */
+function dedupe(addrs) {
+    const seen = new Set();
+    const out = [];
+    for (const a of addrs) {
+        const k = a.toLowerCase();
+        if (!seen.has(k)) {
+            seen.add(k);
+            out.push(a);
+        }
+    }
+    return out;
+}
+/**
+ * Ensure `subject` carries `prefix` exactly once. Existing `Re:`/`Fwd:`/`Fw:`
+ * prefixes (any case) are treated as already-present so we never stack them.
+ */
+export function withSubjectPrefix(subject, prefix) {
+    const s = subject.trim();
+    const present = prefix === "Re:" ? /^re:/i : /^(fwd?|fw):/i;
+    return present.test(s) ? s : `${prefix} ${s}`;
+}
+/** Prefix every line of the original body with `> ` for the quoted reply block. */
+export function quoteBody(plainText) {
+    return plainText
+        .replace(/\s+$/, "")
+        .split(/\r?\n/)
+        .map((l) => (l ? `> ${l}` : ">"))
+        .join("\n");
+}
+/**
+ * Build {@link SmtpSendOptions} for a threaded reply.
+ *
+ * - recipients: `Reply-To` if the original had one, else `From`; with
+ *   `replyAll`, the original `To`+`Cc` (minus our own addresses and the primary
+ *   recipients) become `Cc`.
+ * - subject: `Re: ` prepended unless already present.
+ * - threading: `In-Reply-To` = original `Message-ID`; `References` = original
+ *   chain + that `Message-ID`.
+ * - body: the new text, then an attribution line and the quoted original.
+ */
+export function buildReplyOptions(args) {
+    const { original, originalPlainText, body, replyAll, self, from } = args;
+    const selfSet = new Set(self.filter(Boolean).map((s) => s.toLowerCase()));
+    const to = dedupe((original.replyTo.length ? original.replyTo : original.from).filter(Boolean));
+    const toSet = new Set(to.map((t) => t.toLowerCase()));
+    let cc;
+    if (replyAll) {
+        const extra = dedupe([...original.to, ...original.cc].filter((a) => !selfSet.has(a.toLowerCase()) && !toSet.has(a.toLowerCase())));
+        cc = extra.length ? extra : undefined;
+    }
+    const attribution = buildAttribution(original);
+    const quoted = originalPlainText.trim()
+        ? `\n\n${attribution}${quoteBody(originalPlainText)}`
+        : "";
+    const references = dedupe(original.messageId ? [...original.references, original.messageId] : original.references);
+    return {
+        to,
+        cc,
+        subject: withSubjectPrefix(original.subject, "Re:"),
+        body: `${body}${quoted}`,
+        inReplyTo: original.messageId,
+        references: references.length ? references : undefined,
+        from,
+    };
+}
+/** "On <date>, <sender> wrote:\n" — omits the date clause when unknown. */
+function buildAttribution(original) {
+    const who = original.from[0] ?? original.replyTo[0] ?? "the sender";
+    return original.date ? `On ${original.date}, ${who} wrote:\n` : `${who} wrote:\n`;
+}
+/**
+ * Build {@link SmtpSendOptions} for a forward to new recipients. A forward
+ * starts a new thread, so no `In-Reply-To`/`References` are set — the win over
+ * the AppleScript path is a clean, un-wrapped MIME body.
+ */
+export function buildForwardOptions(args) {
+    const { original, originalPlainText, to, body, from } = args;
+    const headerBlock = [
+        "---------- Forwarded message ----------",
+        original.from.length ? `From: ${original.from.join(", ")}` : "",
+        original.date ? `Date: ${original.date}` : "",
+        `Subject: ${original.subject}`,
+        original.to.length ? `To: ${original.to.join(", ")}` : "",
+        original.cc.length ? `Cc: ${original.cc.join(", ")}` : "",
+    ]
+        .filter(Boolean)
+        .join("\n");
+    const prefix = body?.trim() ? `${body}\n\n` : "";
+    return {
+        to: dedupe(to),
+        subject: withSubjectPrefix(original.subject, "Fwd:"),
+        body: `${prefix}${headerBlock}\n\n${originalPlainText}`,
+        from,
+    };
+}

package/build/services/smtpMailer.d.ts

@@ -36,6 +36,17 @@ export interface SmtpSendOptions {
      * plain-text clients still get a clean fallback.
      */
     htmlBody?: string;
+    /**
+     * RFC 5322 threading (2.5.0): the message this is replying to — emitted as the
+     * `In-Reply-To` header so SMTP replies/forwards thread correctly in Gmail and
+     * other clients. Pass the original message's `Message-ID`.
+     */
+    inReplyTo?: string;
+    /**
+     * RFC 5322 threading (2.5.0): the `References` chain — the original message's
+     * existing `References` plus its `Message-ID`. nodemailer accepts an array.
+     */
+    references?: string[];
 }
 /** Resolved SMTP connection configuration. */
 export interface SmtpConfig {
@@ -114,4 +125,36 @@ export declare function resolveSmtpConfig(env?: NodeJS.ProcessEnv): SmtpConfig;
  * a transporter factory only in tests.
  */
 export declare function sendViaSmtp(opts: SmtpSendOptions, config?: SmtpConfig, createTransport?: typeof nodemailer.createTransport): Promise<SmtpSendResult>;
+/** One recipient of a mail-merge batch (mirrors the AppleScript serial path). */
+export interface SerialSmtpRecipient {
+    email: string;
+    variables: Record<string, string>;
+}
+/** Per-recipient outcome of a serial SMTP send. */
+export interface SerialSmtpResult {
+    email: string;
+    success: boolean;
+    error?: string;
+}
+/**
+ * Replace every `{{Key}}` token in `template` with the matching value from
+ * `variables`. Keys are escaped so regex metacharacters in a key are literal.
+ * Mirrors the substitution in {@link AppleMailManager.sendSerialEmail} so the
+ * two transports personalize identically.
+ */
+export declare function applyPlaceholders(template: string, variables: Record<string, string>): string;
+/**
+ * Send a personalized mail-merge batch over SMTP — one individual message per
+ * recipient (recipients never see each other), with `{{Key}}` placeholders in
+ * the subject/body replaced per recipient. Returns a per-recipient result list;
+ * a single recipient's failure does not abort the batch.
+ *
+ * `opts.send` and `opts.sleep` are injectable for tests (no real SMTP / no real
+ * delay). The default `sleep` waits `delayMs` (clamped 0–10000) between sends.
+ */
+export declare function sendSerialViaSmtp(recipients: SerialSmtpRecipient[], subject: string, body: string, config: SmtpConfig, opts?: {
+    delayMs?: number;
+    send?: typeof sendViaSmtp;
+    sleep?: (ms: number) => Promise<void>;
+}): Promise<SerialSmtpResult[]>;
 //# sourceMappingURL=smtpMailer.d.ts.map

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

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

@@ -198,6 +198,9 @@ export async function sendViaSmtp(opts, config, createTransport = nodemailer.cre
             // When present, nodemailer emits multipart/alternative (text + html).
             html,
             attachments,
+            // RFC 5322 threading for SMTP replies/forwards (2.5.0).
+            inReplyTo: opts.inReplyTo?.trim() || undefined,
+            references: opts.references?.length ? opts.references : undefined,
         });
         return { success: true, messageId: info.messageId };
     }
@@ -211,3 +214,55 @@ export async function sendViaSmtp(opts, config, createTransport = nodemailer.cre
         transporter.close();
     }
 }
+/**
+ * Replace every `{{Key}}` token in `template` with the matching value from
+ * `variables`. Keys are escaped so regex metacharacters in a key are literal.
+ * Mirrors the substitution in {@link AppleMailManager.sendSerialEmail} so the
+ * two transports personalize identically.
+ */
+export function applyPlaceholders(template, variables) {
+    let out = template;
+    for (const [key, value] of Object.entries(variables)) {
+        const safeKey = key.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
+        out = out.replace(new RegExp(`\\{\\{${safeKey}\\}\\}`, "g"), value);
+    }
+    return out;
+}
+/**
+ * Send a personalized mail-merge batch over SMTP — one individual message per
+ * recipient (recipients never see each other), with `{{Key}}` placeholders in
+ * the subject/body replaced per recipient. Returns a per-recipient result list;
+ * a single recipient's failure does not abort the batch.
+ *
+ * `opts.send` and `opts.sleep` are injectable for tests (no real SMTP / no real
+ * delay). The default `sleep` waits `delayMs` (clamped 0–10000) between sends.
+ */
+export async function sendSerialViaSmtp(recipients, subject, body, config, opts = {}) {
+    const send = opts.send ?? sendViaSmtp;
+    const sleep = opts.sleep ?? ((ms) => new Promise((r) => setTimeout(r, ms)));
+    const delay = Math.min(Math.max(opts.delayMs ?? 500, 0), 10000);
+    const results = [];
+    for (let i = 0; i < recipients.length; i++) {
+        const r = recipients[i];
+        try {
+            const res = await send({
+                to: [r.email],
+                subject: applyPlaceholders(subject, r.variables),
+                body: applyPlaceholders(body, r.variables),
+                from: config.from,
+            }, config);
+            results.push({ email: r.email, success: res.success, error: res.error });
+        }
+        catch (error) {
+            results.push({
+                email: r.email,
+                success: false,
+                error: error instanceof Error ? error.message : String(error),
+            });
+        }
+        if (delay > 0 && i < recipients.length - 1) {
+            await sleep(delay);
+        }
+    }
+    return results;
+}

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "apple-mail-mcp",
-  "version": "2.4.2",
+  "version": "2.5.0",
   "description": "MCP server for Apple Mail - read, search, send, and manage emails via Claude and other AI assistants",
   "type": "module",
   "main": "build/index.js",