apple-mail-mcp 2.20.25 → 2.20.27

package/README.md

@@ -501,6 +501,10 @@ Two differences to know when SMTP is auto-preferred:
   or `sentCopy: false` with `sentCopyError`; the field is **absent** when no
   configured IMAP account matches the SMTP identity, which is a skip, not a
   failure. A copy that fails never fails the send — the mail has already gone.
+  Before appending, the Sent mailbox is searched for that `Message-ID`; if the
+  submission server already filed it (Gmail's SMTP always does — the server
+  waits up to ~3 s for it there), nothing is appended and the result adds
+  `sentCopyAlreadyFiled: true` alongside `sentCopy: true`.
   Use `transport: "applescript"` if you want Mail.app itself to file the copy.
 - **`account` is a From override, not account selection.** Over SMTP, `account`
   is used as the From address only when it is an email address; a Mail.app

package/build/cli.js

@@ -58670,6 +58670,8 @@ __export(imapClient_exports, {
   MAX_RFC822_FILE_BYTES: () => MAX_RFC822_FILE_BYTES,
   MAX_RFC822_INLINE_BYTES: () => MAX_RFC822_INLINE_BYTES,
   MAX_UNSCOPED_SEARCH_DEPTH: () => MAX_UNSCOPED_SEARCH_DEPTH,
+  SENT_COPY_GMAIL_POLL_INTERVAL_MS: () => SENT_COPY_GMAIL_POLL_INTERVAL_MS,
+  SENT_COPY_GMAIL_POLL_MS: () => SENT_COPY_GMAIL_POLL_MS,
   __resetPool: () => __resetPool,
   __setPoolConnect: () => __setPoolConnect,
   base64DecodedLength: () => base64DecodedLength,
@@ -58680,6 +58682,7 @@ __export(imapClient_exports, {
   decodedSizeWithoutBody: () => decodedSizeWithoutBody,
   dropAllPools: () => dropAllPools,
   encodeImapId: () => encodeImapId,
+  extractRawMessageId: () => extractRawMessageId,
   flagColorName: () => flagColorName,
   imapAppendDraft: () => imapAppendDraft,
   imapAppendSentCopy: () => imapAppendSentCopy,
@@ -58712,6 +58715,7 @@ __export(imapClient_exports, {
   imapThread: () => imapThread,
   imapUnflagMessage: () => imapUnflagMessage,
   imapUnreadCount: () => imapUnreadCount,
+  isGmailHost: () => isGmailHost,
   isImapAccount: () => isImapAccount,
   listImapAccountLabels: () => listImapAccountLabels,
   mailFlagBitsFor: () => mailFlagBitsFor,
@@ -59840,11 +59844,32 @@ function imapRenameMailbox(oldName, newName, deps = {}) {
     }
   });
 }
-async function imapAppendSentCopy(smtpUser, raw, deps = {}) {
+function isGmailHost(host) {
+  return Boolean(host && GMAIL_HOST.test(host.trim()));
+}
+function extractRawMessageId(raw) {
+  const text = typeof raw === "string" ? raw : raw.toString("latin1");
+  const end = text.search(/\r?\n\r?\n/);
+  const header = (end === -1 ? text : text.slice(0, end)).replace(/\r?\n[ \t]+/g, " ");
+  const m = /^message-id:[ \t]*(<[^<>\s]+>)/im.exec(header);
+  return m ? m[1] : null;
+}
+async function imapAppendSentCopy(smtpUser, raw, deps = {}, opts = {}) {
   if (!deps.config && !isImapAccount(smtpUser)) return { attempted: false };
+  const messageId = extractRawMessageId(raw);
+  const sleep = opts.sleep ?? ((ms) => new Promise((r) => setTimeout(r, ms)));
+  const now = opts.now ?? Date.now;
   try {
-    return await withClient({ ...deps, account: deps.account ?? smtpUser }, async (client) => {
+    return await withClient({ ...deps, account: deps.account ?? smtpUser }, async (client, cfg) => {
       const path3 = await resolveMailboxPath(client, "sent", "list");
+      if (messageId) {
+        const gmail = isGmailHost(cfg.host) || isGmailHost(opts.smtpHost);
+        const budget = gmail ? opts.gmailPollMs ?? SENT_COPY_GMAIL_POLL_MS : 0;
+        const interval = Math.max(1, opts.gmailPollIntervalMs ?? SENT_COPY_GMAIL_POLL_INTERVAL_MS);
+        if (await sentCopyPresent(client, path3, messageId, budget, interval, sleep, now)) {
+          return { attempted: true, success: true, mailbox: path3, alreadyFiled: true };
+        }
+      }
       const res = await client.append(path3, raw, ["\\Seen"]);
       if (!res) throw new Error("server rejected the APPEND (IMAP NO/BAD)");
       return { attempted: true, success: true, mailbox: path3 };
@@ -59853,6 +59878,28 @@ async function imapAppendSentCopy(smtpUser, raw, deps = {}) {
     return { attempted: true, success: false, error: errText(e) };
   }
 }
+async function sentCopyPresent(client, path3, messageId, budget, interval, sleep, now) {
+  const deadline = now() + budget;
+  for (; ; ) {
+    try {
+      const lock = await client.getMailboxLock(path3, { readOnly: true });
+      try {
+        const found = await client.search(
+          { header: { "message-id": messageId }, ...NOT_DELETED },
+          { uid: true }
+        );
+        if (Array.isArray(found) && found.length > 0) return true;
+      } finally {
+        lock.release();
+      }
+    } catch {
+      return false;
+    }
+    const left = deadline - now();
+    if (left <= 0) return false;
+    await sleep(Math.min(interval, left));
+  }
+}
 function resolveDraftImapAccount(account, smtpUser, env = process.env) {
   const specs = listImapAccountSpecs(env);
   const why = "Mail.app's AppleScript cannot set In-Reply-To/References on a draft, so a threaded draft is filed over IMAP into the account's Drafts mailbox";
@@ -60620,7 +60667,7 @@ async function imapThread(id, deps = {}, limit = 50) {
     true
   );
 }
-var import_imapflow, IMAP_ENV, defaultConnect, SPECIAL_USE_ALIASES, NOT_DELETED, LARGE_MAILBOX_MESSAGES, FIRST_SEARCH_WINDOW, MAX_WINDOW, MAX_UNSCOPED_SEARCH_DEPTH, COLOR_FETCH_CHUNK, ROW_QUERY, ROW_QUERY_NO_STRUCTURE, ROW_QUERY_HEADERS_ONLY, DELETED_MARGIN, poolConnect, pools, connecting, MAX_COMPOSE_SOURCE_BYTES, MAX_RFC822_INLINE_BYTES, MAX_RFC822_FILE_BYTES, HEADER_WINDOW_BYTES, MAIL_FLAG_BITS, FLAG_COLOR_NAMES, imapMarkRead, imapMarkUnread, FALLBACK_TRASH_PATH, BASE64_TAIL_WINDOW, QP_EXACT_MAX_BYTES, imapBatchMarkRead, imapBatchMarkUnread, imapBatchFlag, imapBatchUnflag, imapBatchDelete;
+var import_imapflow, IMAP_ENV, defaultConnect, SPECIAL_USE_ALIASES, NOT_DELETED, LARGE_MAILBOX_MESSAGES, FIRST_SEARCH_WINDOW, MAX_WINDOW, MAX_UNSCOPED_SEARCH_DEPTH, COLOR_FETCH_CHUNK, ROW_QUERY, ROW_QUERY_NO_STRUCTURE, ROW_QUERY_HEADERS_ONLY, DELETED_MARGIN, poolConnect, pools, connecting, SENT_COPY_GMAIL_POLL_MS, SENT_COPY_GMAIL_POLL_INTERVAL_MS, GMAIL_HOST, MAX_COMPOSE_SOURCE_BYTES, MAX_RFC822_INLINE_BYTES, MAX_RFC822_FILE_BYTES, HEADER_WINDOW_BYTES, MAIL_FLAG_BITS, FLAG_COLOR_NAMES, imapMarkRead, imapMarkUnread, FALLBACK_TRASH_PATH, BASE64_TAIL_WINDOW, QP_EXACT_MAX_BYTES, imapBatchMarkRead, imapBatchMarkUnread, imapBatchFlag, imapBatchUnflag, imapBatchDelete;
 var init_imapClient = __esm({
   "src/services/imapClient.ts"() {
     "use strict";
@@ -60719,6 +60766,9 @@ var init_imapClient = __esm({
     poolConnect = defaultConnect;
     pools = /* @__PURE__ */ new Map();
     connecting = /* @__PURE__ */ new Map();
+    SENT_COPY_GMAIL_POLL_MS = 3e3;
+    SENT_COPY_GMAIL_POLL_INTERVAL_MS = 500;
+    GMAIL_HOST = /(^|\.)(gmail|googlemail)\.com$/i;
     MAX_COMPOSE_SOURCE_BYTES = 25 * 1024 * 1024;
     MAX_RFC822_INLINE_BYTES = 6 * 1024 * 1024;
     MAX_RFC822_FILE_BYTES = MAX_COMPOSE_SOURCE_BYTES;
@@ -60787,11 +60837,12 @@ import { execFileSync } from "child_process";
 function errText2(e) {
   return e instanceof Error ? e.message : String(e);
 }
-async function defaultAppendSentCopy(smtpUser, raw) {
+async function defaultAppendSentCopy(smtpUser, raw, smtpHost) {
   const { imapAppendSentCopy: imapAppendSentCopy2 } = await Promise.resolve().then(() => (init_imapClient(), imapClient_exports));
-  const result = await imapAppendSentCopy2(smtpUser, raw);
+  const result = await imapAppendSentCopy2(smtpUser, raw, {}, { smtpHost });
   if (!result.attempted) return {};
-  return result.success ? { sentCopy: true } : { sentCopy: false, sentCopyError: result.error };
+  if (!result.success) return { sentCopy: false, sentCopyError: result.error };
+  return result.alreadyFiled ? { sentCopy: true, sentCopyAlreadyFiled: true } : { sentCopy: true };
 }
 function buildRawMime(mail) {
   return new mail_composer_default(mail).compile().build();
@@ -60922,7 +60973,10 @@ async function sendViaSmtp(opts, config, createTransport2 = nodemailer_default.c
     requireTLS,
     auth: { user: cfg.user, pass: cfg.pass }
   });
-  const mailOptions = buildMailOptions(opts, requestedFrom || cfg.from, attachments);
+  const mailOptions = {
+    ...buildMailOptions(opts, requestedFrom || cfg.from, attachments),
+    date: /* @__PURE__ */ new Date()
+  };
   try {
     const info = await transporter.sendMail(mailOptions);
     let copyFields = {};
@@ -60932,7 +60986,7 @@ async function sendViaSmtp(opts, config, createTransport2 = nodemailer_default.c
         keepBcc: true,
         messageId: info.messageId
       });
-      copyFields = await appendSentCopy(cfg.user, raw);
+      copyFields = await appendSentCopy(cfg.user, raw, cfg.host);
     } catch (copyError) {
       copyFields = { sentCopy: false, sentCopyError: errText2(copyError) };
     }

package/build/index.js

@@ -65470,11 +65470,12 @@ import { execFileSync } from "child_process";
 function errText(e) {
   return e instanceof Error ? e.message : String(e);
 }
-async function defaultAppendSentCopy(smtpUser, raw) {
+async function defaultAppendSentCopy(smtpUser, raw, smtpHost) {
   const { imapAppendSentCopy: imapAppendSentCopy2 } = await Promise.resolve().then(() => (init_imapClient(), imapClient_exports));
-  const result = await imapAppendSentCopy2(smtpUser, raw);
+  const result = await imapAppendSentCopy2(smtpUser, raw, {}, { smtpHost });
   if (!result.attempted) return {};
-  return result.success ? { sentCopy: true } : { sentCopy: false, sentCopyError: result.error };
+  if (!result.success) return { sentCopy: false, sentCopyError: result.error };
+  return result.alreadyFiled ? { sentCopy: true, sentCopyAlreadyFiled: true } : { sentCopy: true };
 }
 function buildRawMime(mail) {
   return new mail_composer_default(mail).compile().build();
@@ -65622,7 +65623,10 @@ async function sendViaSmtp(opts, config2, createTransport2 = nodemailer_default.
     requireTLS,
     auth: { user: cfg.user, pass: cfg.pass }
   });
-  const mailOptions = buildMailOptions(opts, requestedFrom || cfg.from, attachments);
+  const mailOptions = {
+    ...buildMailOptions(opts, requestedFrom || cfg.from, attachments),
+    date: /* @__PURE__ */ new Date()
+  };
   try {
     const info = await transporter.sendMail(mailOptions);
     let copyFields = {};
@@ -65632,7 +65636,7 @@ async function sendViaSmtp(opts, config2, createTransport2 = nodemailer_default.
         keepBcc: true,
         messageId: info.messageId
       });
-      copyFields = await appendSentCopy(cfg.user, raw);
+      copyFields = await appendSentCopy(cfg.user, raw, cfg.host);
     } catch (copyError) {
       copyFields = { sentCopy: false, sentCopyError: errText(copyError) };
     }
@@ -66423,6 +66427,8 @@ __export(imapClient_exports, {
   MAX_RFC822_FILE_BYTES: () => MAX_RFC822_FILE_BYTES,
   MAX_RFC822_INLINE_BYTES: () => MAX_RFC822_INLINE_BYTES,
   MAX_UNSCOPED_SEARCH_DEPTH: () => MAX_UNSCOPED_SEARCH_DEPTH,
+  SENT_COPY_GMAIL_POLL_INTERVAL_MS: () => SENT_COPY_GMAIL_POLL_INTERVAL_MS,
+  SENT_COPY_GMAIL_POLL_MS: () => SENT_COPY_GMAIL_POLL_MS,
   __resetPool: () => __resetPool,
   __setPoolConnect: () => __setPoolConnect,
   base64DecodedLength: () => base64DecodedLength,
@@ -66433,6 +66439,7 @@ __export(imapClient_exports, {
   decodedSizeWithoutBody: () => decodedSizeWithoutBody,
   dropAllPools: () => dropAllPools,
   encodeImapId: () => encodeImapId,
+  extractRawMessageId: () => extractRawMessageId,
   flagColorName: () => flagColorName,
   imapAppendDraft: () => imapAppendDraft,
   imapAppendSentCopy: () => imapAppendSentCopy,
@@ -66465,6 +66472,7 @@ __export(imapClient_exports, {
   imapThread: () => imapThread,
   imapUnflagMessage: () => imapUnflagMessage,
   imapUnreadCount: () => imapUnreadCount,
+  isGmailHost: () => isGmailHost,
   isImapAccount: () => isImapAccount,
   listImapAccountLabels: () => listImapAccountLabels,
   mailFlagBitsFor: () => mailFlagBitsFor,
@@ -67593,11 +67601,32 @@ function imapRenameMailbox(oldName, newName, deps = {}) {
     }
   });
 }
-async function imapAppendSentCopy(smtpUser, raw, deps = {}) {
+function isGmailHost(host) {
+  return Boolean(host && GMAIL_HOST.test(host.trim()));
+}
+function extractRawMessageId(raw) {
+  const text = typeof raw === "string" ? raw : raw.toString("latin1");
+  const end = text.search(/\r?\n\r?\n/);
+  const header = (end === -1 ? text : text.slice(0, end)).replace(/\r?\n[ \t]+/g, " ");
+  const m = /^message-id:[ \t]*(<[^<>\s]+>)/im.exec(header);
+  return m ? m[1] : null;
+}
+async function imapAppendSentCopy(smtpUser, raw, deps = {}, opts = {}) {
   if (!deps.config && !isImapAccount(smtpUser)) return { attempted: false };
+  const messageId = extractRawMessageId(raw);
+  const sleep2 = opts.sleep ?? ((ms) => new Promise((r) => setTimeout(r, ms)));
+  const now = opts.now ?? Date.now;
   try {
-    return await withClient({ ...deps, account: deps.account ?? smtpUser }, async (client) => {
+    return await withClient({ ...deps, account: deps.account ?? smtpUser }, async (client, cfg) => {
       const path3 = await resolveMailboxPath(client, "sent", "list");
+      if (messageId) {
+        const gmail = isGmailHost(cfg.host) || isGmailHost(opts.smtpHost);
+        const budget = gmail ? opts.gmailPollMs ?? SENT_COPY_GMAIL_POLL_MS : 0;
+        const interval = Math.max(1, opts.gmailPollIntervalMs ?? SENT_COPY_GMAIL_POLL_INTERVAL_MS);
+        if (await sentCopyPresent(client, path3, messageId, budget, interval, sleep2, now)) {
+          return { attempted: true, success: true, mailbox: path3, alreadyFiled: true };
+        }
+      }
       const res = await client.append(path3, raw, ["\\Seen"]);
       if (!res) throw new Error("server rejected the APPEND (IMAP NO/BAD)");
       return { attempted: true, success: true, mailbox: path3 };
@@ -67606,6 +67635,28 @@ async function imapAppendSentCopy(smtpUser, raw, deps = {}) {
     return { attempted: true, success: false, error: errText2(e) };
   }
 }
+async function sentCopyPresent(client, path3, messageId, budget, interval, sleep2, now) {
+  const deadline = now() + budget;
+  for (; ; ) {
+    try {
+      const lock = await client.getMailboxLock(path3, { readOnly: true });
+      try {
+        const found = await client.search(
+          { header: { "message-id": messageId }, ...NOT_DELETED },
+          { uid: true }
+        );
+        if (Array.isArray(found) && found.length > 0) return true;
+      } finally {
+        lock.release();
+      }
+    } catch {
+      return false;
+    }
+    const left = deadline - now();
+    if (left <= 0) return false;
+    await sleep2(Math.min(interval, left));
+  }
+}
 function resolveDraftImapAccount(account, smtpUser, env = process.env) {
   const specs = listImapAccountSpecs(env);
   const why = "Mail.app's AppleScript cannot set In-Reply-To/References on a draft, so a threaded draft is filed over IMAP into the account's Drafts mailbox";
@@ -68373,7 +68424,7 @@ async function imapThread(id, deps = {}, limit = 50) {
     true
   );
 }
-var import_imapflow, IMAP_ENV, defaultConnect, SPECIAL_USE_ALIASES, NOT_DELETED, LARGE_MAILBOX_MESSAGES, FIRST_SEARCH_WINDOW, MAX_WINDOW, MAX_UNSCOPED_SEARCH_DEPTH, COLOR_FETCH_CHUNK, ROW_QUERY, ROW_QUERY_NO_STRUCTURE, ROW_QUERY_HEADERS_ONLY, DELETED_MARGIN, poolConnect, pools, connecting, MAX_COMPOSE_SOURCE_BYTES, MAX_RFC822_INLINE_BYTES, MAX_RFC822_FILE_BYTES, HEADER_WINDOW_BYTES, MAIL_FLAG_BITS, FLAG_COLOR_NAMES, imapMarkRead, imapMarkUnread, FALLBACK_TRASH_PATH, BASE64_TAIL_WINDOW, QP_EXACT_MAX_BYTES, imapBatchMarkRead, imapBatchMarkUnread, imapBatchFlag, imapBatchUnflag, imapBatchDelete;
+var import_imapflow, IMAP_ENV, defaultConnect, SPECIAL_USE_ALIASES, NOT_DELETED, LARGE_MAILBOX_MESSAGES, FIRST_SEARCH_WINDOW, MAX_WINDOW, MAX_UNSCOPED_SEARCH_DEPTH, COLOR_FETCH_CHUNK, ROW_QUERY, ROW_QUERY_NO_STRUCTURE, ROW_QUERY_HEADERS_ONLY, DELETED_MARGIN, poolConnect, pools, connecting, SENT_COPY_GMAIL_POLL_MS, SENT_COPY_GMAIL_POLL_INTERVAL_MS, GMAIL_HOST, MAX_COMPOSE_SOURCE_BYTES, MAX_RFC822_INLINE_BYTES, MAX_RFC822_FILE_BYTES, HEADER_WINDOW_BYTES, MAIL_FLAG_BITS, FLAG_COLOR_NAMES, imapMarkRead, imapMarkUnread, FALLBACK_TRASH_PATH, BASE64_TAIL_WINDOW, QP_EXACT_MAX_BYTES, imapBatchMarkRead, imapBatchMarkUnread, imapBatchFlag, imapBatchUnflag, imapBatchDelete;
 var init_imapClient = __esm({
   "src/services/imapClient.ts"() {
     "use strict";
@@ -68472,6 +68523,9 @@ var init_imapClient = __esm({
     poolConnect = defaultConnect;
     pools = /* @__PURE__ */ new Map();
     connecting = /* @__PURE__ */ new Map();
+    SENT_COPY_GMAIL_POLL_MS = 3e3;
+    SENT_COPY_GMAIL_POLL_INTERVAL_MS = 500;
+    GMAIL_HOST = /(^|\.)(gmail|googlemail)\.com$/i;
     MAX_COMPOSE_SOURCE_BYTES = 25 * 1024 * 1024;
     MAX_RFC822_INLINE_BYTES = 6 * 1024 * 1024;
     MAX_RFC822_FILE_BYTES = MAX_COMPOSE_SOURCE_BYTES;
@@ -85682,7 +85736,8 @@ ${indent}end try${this.sanitizeFragment("_uacct", indent)}${this.sanitizeFragmen
    */
   resolveById(id, innerAction, hint, opts = {}) {
     const remembered = this.idLocationIndex.get(String(id));
-    const loc = hint?.account && hint?.mailbox ? { account: hint.account, mailbox: hint.mailbox, explicit: true } : remembered ? { ...remembered, explicit: false } : void 0;
+    const usable = hint?.account && remembered && remembered.account !== hint.account ? void 0 : remembered;
+    const loc = hint?.account && hint?.mailbox ? { account: hint.account, mailbox: hint.mailbox, explicit: true } : usable ? { ...usable, explicit: false } : void 0;
     if (loc) {
       const scoped = this.resolveScopedById(id, loc, innerAction);
       if (scoped.kind === "hit") return scoped.output;
@@ -89276,7 +89331,8 @@ async function runCompose(deps, args) {
           // Best-effort Sent-folder copy (issue #220) — same field shape as
           // send-email, since it's the same sendViaSmtp underneath.
           ...result.sentCopy !== void 0 ? { sentCopy: result.sentCopy } : {},
-          ...result.sentCopyError !== void 0 ? { sentCopyError: result.sentCopyError } : {}
+          ...result.sentCopyError !== void 0 ? { sentCopyError: result.sentCopyError } : {},
+          ...result.sentCopyAlreadyFiled ? { sentCopyAlreadyFiled: true } : {}
         }
       );
     } catch (error3) {
@@ -91046,6 +91102,9 @@ var SENT_COPY_SCHEMA = external_exports.boolean().optional().describe(
   "SMTP only: whether a best-effort copy was filed to the account's Sent mailbox over IMAP (issue #220). Absent when no configured IMAP account matches the SMTP identity \u2014 not a failure, the feature simply wasn't engaged."
 );
 var SENT_COPY_ERROR_SCHEMA = external_exports.string().optional().describe("Present only when sentCopy is false: why the Sent-folder copy failed.");
+var SENT_COPY_ALREADY_FILED_SCHEMA = external_exports.boolean().optional().describe(
+  "Present (true) only when sentCopy is true because the Sent mailbox already held this Message-ID (e.g. Gmail's SMTP files its own copy), so none was appended."
+);
 var SEND_ACCOUNT_SCHEMA = external_exports.string().optional().describe(
   "Account to send from. AppleScript transport: a Mail account name or an exact sender address, resolved to one address and verified before sending; if it matches no enabled account, or Mail would use a different sender, nothing is sent and an error is returned. Omitted \u2192 Mail's default sender (reported back in `from`). SMTP transport: an email-form From override (see README)."
 );
@@ -91078,7 +91137,8 @@ registerTool(
       from: external_exports.string().optional().describe("AppleScript transport: the sender Mail.app used"),
       messageId: external_exports.string().optional(),
       sentCopy: SENT_COPY_SCHEMA,
-      sentCopyError: SENT_COPY_ERROR_SCHEMA
+      sentCopyError: SENT_COPY_ERROR_SCHEMA,
+      sentCopyAlreadyFiled: SENT_COPY_ALREADY_FILED_SCHEMA
     }
   },
   withErrorHandling(
@@ -91116,7 +91176,7 @@ registerTool(
         if (!result.success) {
           return errorResponse(result.error ?? "Failed to send email via SMTP.");
         }
-        const copyNote = result.sentCopy === true ? " (Sent-folder copy filed)" : result.sentCopy === false ? ` (Sent-folder copy NOT filed: ${result.sentCopyError ?? "unknown error"})` : "";
+        const copyNote = result.sentCopy === true ? result.sentCopyAlreadyFiled ? " (Sent-folder copy already filed by the server)" : " (Sent-folder copy filed)" : result.sentCopy === false ? ` (Sent-folder copy NOT filed: ${result.sentCopyError ?? "unknown error"})` : "";
         return successResponse(`Email sent via SMTP to ${to.join(", ")}${attachInfo}${copyNote}`, {
           ok: true,
           recipients: to,
@@ -91124,7 +91184,8 @@ registerTool(
           transport: "smtp",
           ...result.messageId ? { messageId: result.messageId } : {},
           ...result.sentCopy !== void 0 ? { sentCopy: result.sentCopy } : {},
-          ...result.sentCopyError !== void 0 ? { sentCopyError: result.sentCopyError } : {}
+          ...result.sentCopyError !== void 0 ? { sentCopyError: result.sentCopyError } : {},
+          ...result.sentCopyAlreadyFiled ? { sentCopyAlreadyFiled: true } : {}
         });
       }
       const sent = mailManager.sendEmail(to, subject, body, cc, bcc, account, attachments);
@@ -91333,7 +91394,8 @@ registerTool(
       id: external_exports.string().optional(),
       attachmentCount: external_exports.number().optional(),
       sentCopy: SENT_COPY_SCHEMA,
-      sentCopyError: SENT_COPY_ERROR_SCHEMA
+      sentCopyError: SENT_COPY_ERROR_SCHEMA,
+      sentCopyAlreadyFiled: SENT_COPY_ALREADY_FILED_SCHEMA
     }
   },
   withErrorHandling((args) => runReply(composeDeps, args), "Error replying to message")
@@ -91359,7 +91421,8 @@ registerTool(
       id: external_exports.string().optional(),
       attachmentCount: external_exports.number().optional(),
       sentCopy: SENT_COPY_SCHEMA,
-      sentCopyError: SENT_COPY_ERROR_SCHEMA
+      sentCopyError: SENT_COPY_ERROR_SCHEMA,
+      sentCopyAlreadyFiled: SENT_COPY_ALREADY_FILED_SCHEMA
     }
   },
   withErrorHandling((args) => runForward(composeDeps, args), "Error forwarding message")

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "apple-mail-mcp",
-  "version": "2.20.25",
+  "version": "2.20.27",
   "description": "MCP server for Apple Mail - read, search, send, and manage emails via Claude and other AI assistants",
   "type": "module",
   "main": "build/index.js",