@upyo/smtp 0.1.0 → 0.1.2-dev.50

package/LICENSE

@@ -0,0 +1,20 @@
+MIT License
+
+Copyright 2025 Hong Minhee
+
+Permission is hereby granted, free of charge, to any person obtaining a copy of
+this software and associated documentation files (the "Software"), to deal in
+the Software without restriction, including without limitation the rights to
+use, copy, modify, merge, publish, distribute, sublicense, and/or sell copies of
+the Software, and to permit persons to whom the Software is furnished to do so,
+subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER
+IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN
+CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.

package/README.md

@@ -30,12 +30,7 @@ Features
  -  Comprehensive testing utilities
  -  TypeScript support
  -  Cross-runtime compatibility (Node.js, Bun, Deno)
-
-
-TODO
-----
-
-- [ ] STARTTLS support (currently only supports direct TLS)
+ -  STARTTLS support for secure connection upgrade
 
 
 Installation

package/dist/index.cjs

@@ -186,6 +186,49 @@ var SmtpConnection = class {
 		if (response.code !== 250) throw new Error(`EHLO failed: ${response.message}`);
 		this.capabilities = response.raw.split("\r\n").filter((line) => line.startsWith("250-") || line.startsWith("250 ")).map((line) => line.substring(4)).filter((line) => line.length > 0);
 	}
+	async starttls(signal) {
+		if (!this.socket) throw new Error("Not connected");
+		if (this.socket instanceof node_tls.TLSSocket) throw new Error("Connection is already using TLS");
+		signal?.throwIfAborted();
+		const response = await this.sendCommand("STARTTLS", signal);
+		if (response.code !== 220) throw new Error(`STARTTLS failed: ${response.message}`);
+		signal?.throwIfAborted();
+		return new Promise((resolve, reject) => {
+			const timeout = setTimeout(() => {
+				this.socket?.destroy();
+				reject(/* @__PURE__ */ new Error("STARTTLS upgrade timeout"));
+			}, this.config.connectionTimeout);
+			const plainSocket = this.socket;
+			const tlsSocket = (0, node_tls.connect)({
+				socket: plainSocket,
+				host: this.config.host,
+				rejectUnauthorized: this.config.tls?.rejectUnauthorized ?? true,
+				ca: this.config.tls?.ca,
+				key: this.config.tls?.key,
+				cert: this.config.tls?.cert,
+				minVersion: this.config.tls?.minVersion,
+				maxVersion: this.config.tls?.maxVersion
+			});
+			const onSecureConnect = () => {
+				clearTimeout(timeout);
+				this.socket = tlsSocket;
+				this.socket.setTimeout(this.config.socketTimeout);
+				resolve();
+			};
+			const onError = (error) => {
+				clearTimeout(timeout);
+				tlsSocket.destroy();
+				reject(error);
+			};
+			tlsSocket.once("secureConnect", onSecureConnect);
+			tlsSocket.once("error", onError);
+			tlsSocket.once("timeout", () => {
+				clearTimeout(timeout);
+				tlsSocket.destroy();
+				reject(/* @__PURE__ */ new Error("TLS upgrade timeout"));
+			});
+		});
+	}
 	async authenticate(signal) {
 		if (!this.config.auth) return;
 		if (this.authenticated) return;
@@ -278,10 +321,10 @@ async function buildRawMessage(message) {
 	const hasHtml = "html" in message.content;
 	const hasText = "text" in message.content;
 	const isMultipart = hasAttachments || hasHtml && hasText;
-	lines.push(`From: ${(0, __upyo_core.formatAddress)(message.sender)}`);
-	lines.push(`To: ${message.recipients.map(__upyo_core.formatAddress).join(", ")}`);
-	if (message.ccRecipients.length > 0) lines.push(`Cc: ${message.ccRecipients.map(__upyo_core.formatAddress).join(", ")}`);
-	if (message.replyRecipients.length > 0) lines.push(`Reply-To: ${message.replyRecipients.map(__upyo_core.formatAddress).join(", ")}`);
+	lines.push(`From: ${encodeHeaderValue((0, __upyo_core.formatAddress)(message.sender))}`);
+	lines.push(`To: ${encodeHeaderValue(message.recipients.map(__upyo_core.formatAddress).join(", "))}`);
+	if (message.ccRecipients.length > 0) lines.push(`Cc: ${encodeHeaderValue(message.ccRecipients.map(__upyo_core.formatAddress).join(", "))}`);
+	if (message.replyRecipients.length > 0) lines.push(`Reply-To: ${encodeHeaderValue(message.replyRecipients.map(__upyo_core.formatAddress).join(", "))}`);
 	lines.push(`Subject: ${encodeHeaderValue(message.subject)}`);
 	lines.push(`Date: ${(/* @__PURE__ */ new Date()).toUTCString()}`);
 	lines.push(`Message-ID: <${generateMessageId()}>`);
@@ -365,17 +408,48 @@ function encodeHeaderValue(value) {
 	if (!/^[\x20-\x7E]*$/.test(value)) {
 		const utf8Bytes = new TextEncoder().encode(value);
 		const base64 = btoa(String.fromCharCode(...utf8Bytes));
-		return `=?UTF-8?B?${base64}?=`;
+		const maxEncodedLength = 75;
+		const encodedWord = `=?UTF-8?B?${base64}?=`;
+		if (encodedWord.length <= maxEncodedLength) return encodedWord;
+		const words = [];
+		let currentBase64 = "";
+		for (let i = 0; i < base64.length; i += 4) {
+			const chunk = base64.slice(i, i + 4);
+			const testWord = `=?UTF-8?B?${currentBase64}${chunk}?=`;
+			if (testWord.length <= maxEncodedLength) currentBase64 += chunk;
+			else {
+				if (currentBase64) words.push(`=?UTF-8?B?${currentBase64}?=`);
+				currentBase64 = chunk;
+			}
+		}
+		if (currentBase64) words.push(`=?UTF-8?B?${currentBase64}?=`);
+		return words.join(" ");
 	}
 	return value;
 }
 function encodeQuotedPrintable(text) {
-	return text.replace(/[^\x20-\x7E]/g, (char) => {
-		const code = char.charCodeAt(0);
-		if (code < 256) return `=${code.toString(16).toUpperCase().padStart(2, "0")}`;
-		const utf8 = new TextEncoder().encode(char);
-		return Array.from(utf8).map((byte) => `=${byte.toString(16).toUpperCase().padStart(2, "0")}`).join("");
-	}).replace(/=$/gm, "=3D").replace(/^\./, "=2E");
+	const utf8Bytes = new TextEncoder().encode(text);
+	let result = "";
+	let lineLength = 0;
+	const maxLineLength = 76;
+	for (let i = 0; i < utf8Bytes.length; i++) {
+		const byte = utf8Bytes[i];
+		let encoded = "";
+		if (byte < 32 || byte > 126 || byte === 61 || byte === 46 && lineLength === 0) encoded = `=${byte.toString(16).toUpperCase().padStart(2, "0")}`;
+		else encoded = String.fromCharCode(byte);
+		if (lineLength + encoded.length > maxLineLength) {
+			result += "=\r\n";
+			lineLength = 0;
+		}
+		result += encoded;
+		lineLength += encoded.length;
+		if (byte === 13 && i + 1 < utf8Bytes.length && utf8Bytes[i + 1] === 10) {
+			i++;
+			result += String.fromCharCode(10);
+			lineLength = 0;
+		} else if (byte === 10 && (i === 0 || utf8Bytes[i - 1] !== 13)) lineLength = 0;
+	}
+	return result;
 }
 function encodeBase64(data) {
 	const base64 = btoa(String.fromCharCode(...data));
@@ -591,6 +665,12 @@ var SmtpTransport = class {
 		signal?.throwIfAborted();
 		await connection.ehlo(signal);
 		signal?.throwIfAborted();
+		if (!this.config.secure && connection.capabilities.some((cap) => cap.toUpperCase().startsWith("STARTTLS"))) {
+			await connection.starttls(signal);
+			signal?.throwIfAborted();
+			await connection.ehlo(signal);
+			signal?.throwIfAborted();
+		}
 		await connection.authenticate(signal);
 	}
 	async returnConnection(connection) {

package/dist/index.js

@@ -1,5 +1,5 @@
 import { Socket } from "node:net";
-import { connect } from "node:tls";
+import { TLSSocket, connect } from "node:tls";
 import { formatAddress } from "@upyo/core";
 
 //#region src/config.ts
@@ -163,6 +163,49 @@ var SmtpConnection = class {
 		if (response.code !== 250) throw new Error(`EHLO failed: ${response.message}`);
 		this.capabilities = response.raw.split("\r\n").filter((line) => line.startsWith("250-") || line.startsWith("250 ")).map((line) => line.substring(4)).filter((line) => line.length > 0);
 	}
+	async starttls(signal) {
+		if (!this.socket) throw new Error("Not connected");
+		if (this.socket instanceof TLSSocket) throw new Error("Connection is already using TLS");
+		signal?.throwIfAborted();
+		const response = await this.sendCommand("STARTTLS", signal);
+		if (response.code !== 220) throw new Error(`STARTTLS failed: ${response.message}`);
+		signal?.throwIfAborted();
+		return new Promise((resolve, reject) => {
+			const timeout = setTimeout(() => {
+				this.socket?.destroy();
+				reject(/* @__PURE__ */ new Error("STARTTLS upgrade timeout"));
+			}, this.config.connectionTimeout);
+			const plainSocket = this.socket;
+			const tlsSocket = connect({
+				socket: plainSocket,
+				host: this.config.host,
+				rejectUnauthorized: this.config.tls?.rejectUnauthorized ?? true,
+				ca: this.config.tls?.ca,
+				key: this.config.tls?.key,
+				cert: this.config.tls?.cert,
+				minVersion: this.config.tls?.minVersion,
+				maxVersion: this.config.tls?.maxVersion
+			});
+			const onSecureConnect = () => {
+				clearTimeout(timeout);
+				this.socket = tlsSocket;
+				this.socket.setTimeout(this.config.socketTimeout);
+				resolve();
+			};
+			const onError = (error) => {
+				clearTimeout(timeout);
+				tlsSocket.destroy();
+				reject(error);
+			};
+			tlsSocket.once("secureConnect", onSecureConnect);
+			tlsSocket.once("error", onError);
+			tlsSocket.once("timeout", () => {
+				clearTimeout(timeout);
+				tlsSocket.destroy();
+				reject(/* @__PURE__ */ new Error("TLS upgrade timeout"));
+			});
+		});
+	}
 	async authenticate(signal) {
 		if (!this.config.auth) return;
 		if (this.authenticated) return;
@@ -255,10 +298,10 @@ async function buildRawMessage(message) {
 	const hasHtml = "html" in message.content;
 	const hasText = "text" in message.content;
 	const isMultipart = hasAttachments || hasHtml && hasText;
-	lines.push(`From: ${formatAddress(message.sender)}`);
-	lines.push(`To: ${message.recipients.map(formatAddress).join(", ")}`);
-	if (message.ccRecipients.length > 0) lines.push(`Cc: ${message.ccRecipients.map(formatAddress).join(", ")}`);
-	if (message.replyRecipients.length > 0) lines.push(`Reply-To: ${message.replyRecipients.map(formatAddress).join(", ")}`);
+	lines.push(`From: ${encodeHeaderValue(formatAddress(message.sender))}`);
+	lines.push(`To: ${encodeHeaderValue(message.recipients.map(formatAddress).join(", "))}`);
+	if (message.ccRecipients.length > 0) lines.push(`Cc: ${encodeHeaderValue(message.ccRecipients.map(formatAddress).join(", "))}`);
+	if (message.replyRecipients.length > 0) lines.push(`Reply-To: ${encodeHeaderValue(message.replyRecipients.map(formatAddress).join(", "))}`);
 	lines.push(`Subject: ${encodeHeaderValue(message.subject)}`);
 	lines.push(`Date: ${(/* @__PURE__ */ new Date()).toUTCString()}`);
 	lines.push(`Message-ID: <${generateMessageId()}>`);
@@ -342,17 +385,48 @@ function encodeHeaderValue(value) {
 	if (!/^[\x20-\x7E]*$/.test(value)) {
 		const utf8Bytes = new TextEncoder().encode(value);
 		const base64 = btoa(String.fromCharCode(...utf8Bytes));
-		return `=?UTF-8?B?${base64}?=`;
+		const maxEncodedLength = 75;
+		const encodedWord = `=?UTF-8?B?${base64}?=`;
+		if (encodedWord.length <= maxEncodedLength) return encodedWord;
+		const words = [];
+		let currentBase64 = "";
+		for (let i = 0; i < base64.length; i += 4) {
+			const chunk = base64.slice(i, i + 4);
+			const testWord = `=?UTF-8?B?${currentBase64}${chunk}?=`;
+			if (testWord.length <= maxEncodedLength) currentBase64 += chunk;
+			else {
+				if (currentBase64) words.push(`=?UTF-8?B?${currentBase64}?=`);
+				currentBase64 = chunk;
+			}
+		}
+		if (currentBase64) words.push(`=?UTF-8?B?${currentBase64}?=`);
+		return words.join(" ");
 	}
 	return value;
 }
 function encodeQuotedPrintable(text) {
-	return text.replace(/[^\x20-\x7E]/g, (char) => {
-		const code = char.charCodeAt(0);
-		if (code < 256) return `=${code.toString(16).toUpperCase().padStart(2, "0")}`;
-		const utf8 = new TextEncoder().encode(char);
-		return Array.from(utf8).map((byte) => `=${byte.toString(16).toUpperCase().padStart(2, "0")}`).join("");
-	}).replace(/=$/gm, "=3D").replace(/^\./, "=2E");
+	const utf8Bytes = new TextEncoder().encode(text);
+	let result = "";
+	let lineLength = 0;
+	const maxLineLength = 76;
+	for (let i = 0; i < utf8Bytes.length; i++) {
+		const byte = utf8Bytes[i];
+		let encoded = "";
+		if (byte < 32 || byte > 126 || byte === 61 || byte === 46 && lineLength === 0) encoded = `=${byte.toString(16).toUpperCase().padStart(2, "0")}`;
+		else encoded = String.fromCharCode(byte);
+		if (lineLength + encoded.length > maxLineLength) {
+			result += "=\r\n";
+			lineLength = 0;
+		}
+		result += encoded;
+		lineLength += encoded.length;
+		if (byte === 13 && i + 1 < utf8Bytes.length && utf8Bytes[i + 1] === 10) {
+			i++;
+			result += String.fromCharCode(10);
+			lineLength = 0;
+		} else if (byte === 10 && (i === 0 || utf8Bytes[i - 1] !== 13)) lineLength = 0;
+	}
+	return result;
 }
 function encodeBase64(data) {
 	const base64 = btoa(String.fromCharCode(...data));
@@ -568,6 +642,12 @@ var SmtpTransport = class {
 		signal?.throwIfAborted();
 		await connection.ehlo(signal);
 		signal?.throwIfAborted();
+		if (!this.config.secure && connection.capabilities.some((cap) => cap.toUpperCase().startsWith("STARTTLS"))) {
+			await connection.starttls(signal);
+			signal?.throwIfAborted();
+			await connection.ehlo(signal);
+			signal?.throwIfAborted();
+		}
 		await connection.authenticate(signal);
 	}
 	async returnConnection(connection) {

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@upyo/smtp",
-  "version": "0.1.0",
+  "version": "0.1.2-dev.50+2a829bef",
   "description": "SMTP transport for Upyo email library",
   "keywords": [
     "email",
@@ -53,7 +53,7 @@
   },
   "sideEffects": false,
   "peerDependencies": {
-    "@upyo/core": "0.1.0"
+    "@upyo/core": "0.1.2-dev.50+2a829bef"
   },
   "devDependencies": {
     "@dotenvx/dotenvx": "^1.47.3",