@upyo/smtp 0.1.0-dev.9 → 0.1.1

package/README.md

@@ -3,7 +3,16 @@
 @upyo/smtp
 ==========
 
-SMTP transport implementation for the Upyo email library.
+[![JSR][JSR badge]][JSR]
+[![npm][npm badge]][npm]
+
+SMTP transport implementation for the [Upyo] email library.
+
+[JSR]: https://jsr.io/@upyo/smtp
+[JSR badge]: https://jsr.io/badges/@upyo/smtp
+[npm]: https://www.npmjs.com/package/@upyo/smtp
+[npm badge]: https://img.shields.io/npm/v/@upyo/smtp?logo=npm
+[Upyo]: https://upyo.org/
 
 
 Features
@@ -47,8 +56,8 @@ Usage
 ### Basic Email Sending
 
 ~~~~ typescript
+import { createMessage } from "@upyo/core";
 import { SmtpTransport } from "@upyo/smtp";
-import { type Message } from "@upyo/core";
 
 const transport = new SmtpTransport({
   host: "smtp.example.com",
@@ -60,53 +69,19 @@ const transport = new SmtpTransport({
   },
 });
 
-const message: Message = {
-  sender: { name: "John Doe", address: "john@example.com" },
-  recipients: [{ name: "Jane Doe", address: "jane@example.com" }],
-  ccRecipients: [],
-  bccRecipients: [],
-  replyRecipients: [],
+const message = createMessage({
+  from: "sender@example.com",
+  to: "recipient@example.net",
   subject: "Hello from Upyo!",
   content: { text: "This is a test email." },
-  attachments: [],
-  priority: "normal",
-  tags: [],
-  headers: new Headers(),
-};
-
-const receipt = await transport.send(message);
-console.log("Email sent:", receipt.successful);
-~~~~
-
-### HTML Email with Attachments
-
-~~~~ typescript
-const message: Message = {
-  sender: { address: "sender@example.com" },
-  recipients: [{ address: "recipient@example.com" }],
-  ccRecipients: [],
-  bccRecipients: [],
-  replyRecipients: [],
-  subject: "HTML Email with Attachment",
-  content: {
-    html: "<h1>Hello!</h1><p>This is an <strong>HTML</strong> email.</p>",
-    text: "Hello!\nThis is an HTML email.",
-  },
-  attachments: [
-    {
-      filename: "document.pdf",
-      content: new Uint8Array(pdfBytes),
-      contentType: "application/pdf",
-      contentId: "doc1",
-      inline: false,
-    },
-  ],
-  priority: "high",
-  tags: ["newsletter"],
-  headers: new Headers([["X-Campaign-ID", "12345"]]),
-};
+});
 
 const receipt = await transport.send(message);
+if (receipt.successful) {
+  console.log("Message sent with ID:", receipt.messageId);
+} else {
+  console.error("Send failed:", receipt.errorMessages.join(", "));
+}
 ~~~~
 
 ### Sending Multiple Emails
@@ -115,7 +90,11 @@ const receipt = await transport.send(message);
 const messages = [message1, message2, message3];
 
 for await (const receipt of transport.sendMany(messages)) {
-  console.log(`Email ${receipt.messageId}: ${receipt.successful ? "sent" : "failed"}`);
+  if (receipt.successful) {
+    console.log(`Email sent with ID: ${receipt.messageId}`);
+  } else {
+    console.error(`Email failed: ${receipt.errorMessages.join(", ")}`);
+  }
 }
 ~~~~
 

package/dist/index.cjs

@@ -31,21 +31,11 @@ const __upyo_core = __toESM(require("@upyo/core"));
 *
 * This function takes a partial SMTP configuration and returns a complete
 * configuration with all optional fields filled with sensible defaults.
+* It is used internally by the SMTP transport.
 *
 * @param config - The SMTP configuration with optional fields
 * @returns A resolved configuration with all defaults applied
-*
-* @example
-* ```typescript
-* const resolved = createSmtpConfig({
-*   host: 'smtp.example.com',
-*   auth: { user: 'user', pass: 'pass' }
-* });
-*
-* // resolved.port will be 587 (default)
-* // resolved.secure will be true (default)
-* // resolved.poolSize will be 5 (default)
-* ```
+* @internal
 */
 function createSmtpConfig(config) {
 	return {
@@ -266,7 +256,7 @@ var SmtpConnection = class {
 
 //#endregion
 //#region src/message-converter.ts
-function convertMessage(message) {
+async function convertMessage(message) {
 	const envelope = {
 		from: message.sender.address,
 		to: [
@@ -275,23 +265,23 @@ function convertMessage(message) {
 			...message.bccRecipients.map((r) => r.address)
 		]
 	};
-	const raw = buildRawMessage(message);
+	const raw = await buildRawMessage(message);
 	return {
 		envelope,
 		raw
 	};
 }
-function buildRawMessage(message) {
+async function buildRawMessage(message) {
 	const lines = [];
 	const boundary = generateBoundary();
 	const hasAttachments = message.attachments.length > 0;
 	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()}>`);
@@ -346,7 +336,7 @@ function buildRawMessage(message) {
 				lines.push(`Content-ID: <${attachment.contentId}>`);
 			} else lines.push(`Content-Disposition: attachment; filename="${attachment.filename}"`);
 			lines.push("");
-			lines.push(encodeBase64(attachment.content));
+			lines.push(encodeBase64(await attachment.content));
 		}
 		lines.push("");
 		lines.push(`--${boundary}--`);
@@ -375,17 +365,48 @@ function encodeHeaderValue(value) {
 	if (!/^[\x20-\x7E]*$/.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));
@@ -428,9 +449,15 @@ function encodeBase64(data) {
 * ```
 */
 var SmtpTransport = class {
+	/**
+	* The SMTP configuration used by this transport.
+	*/
 	config;
-	connectionPool = [];
+	/**
+	* The maximum number of connections in the pool.
+	*/
 	poolSize;
+	connectionPool = [];
 	/**
 	* Creates a new SMTP transport instance.
 	*
@@ -472,21 +499,19 @@ var SmtpTransport = class {
 		const connection = await this.getConnection(options?.signal);
 		try {
 			options?.signal?.throwIfAborted();
-			const smtpMessage = convertMessage(message);
+			const smtpMessage = await convertMessage(message);
 			options?.signal?.throwIfAborted();
 			const messageId = await connection.sendMessage(smtpMessage, options?.signal);
 			await this.returnConnection(connection);
 			return {
-				messageId,
-				errorMessages: [],
-				successful: true
+				successful: true,
+				messageId
 			};
 		} catch (error) {
 			await this.discardConnection(connection);
 			return {
-				messageId: "",
-				errorMessages: [error instanceof Error ? error.message : String(error)],
-				successful: false
+				successful: false,
+				errorMessages: [error instanceof Error ? error.message : String(error)]
 			};
 		}
 	}
@@ -528,27 +553,24 @@ var SmtpTransport = class {
 				options?.signal?.throwIfAborted();
 				if (!connectionValid) {
 					yield {
-						messageId: "",
-						errorMessages: ["Connection is no longer valid"],
-						successful: false
+						successful: false,
+						errorMessages: ["Connection is no longer valid"]
 					};
 					continue;
 				}
 				try {
-					const smtpMessage = convertMessage(message);
+					const smtpMessage = await convertMessage(message);
 					options?.signal?.throwIfAborted();
 					const messageId = await connection.sendMessage(smtpMessage, options?.signal);
 					yield {
-						messageId,
-						errorMessages: [],
-						successful: true
+						successful: true,
+						messageId
 					};
 				} catch (error) {
 					connectionValid = false;
 					yield {
-						messageId: "",
-						errorMessages: [error instanceof Error ? error.message : String(error)],
-						successful: false
+						successful: false,
+						errorMessages: [error instanceof Error ? error.message : String(error)]
 					};
 				}
 			}
@@ -556,27 +578,24 @@ var SmtpTransport = class {
 				options?.signal?.throwIfAborted();
 				if (!connectionValid) {
 					yield {
-						messageId: "",
-						errorMessages: ["Connection is no longer valid"],
-						successful: false
+						successful: false,
+						errorMessages: ["Connection is no longer valid"]
 					};
 					continue;
 				}
 				try {
-					const smtpMessage = convertMessage(message);
+					const smtpMessage = await convertMessage(message);
 					options?.signal?.throwIfAborted();
 					const messageId = await connection.sendMessage(smtpMessage, options?.signal);
 					yield {
-						messageId,
-						errorMessages: [],
-						successful: true
+						successful: true,
+						messageId
 					};
 				} catch (error) {
 					connectionValid = false;
 					yield {
-						messageId: "",
-						errorMessages: [error instanceof Error ? error.message : String(error)],
-						successful: false
+						successful: false,
+						errorMessages: [error instanceof Error ? error.message : String(error)]
 					};
 				}
 			}
@@ -661,5 +680,4 @@ var SmtpTransport = class {
 };
 
 //#endregion
-exports.SmtpTransport = SmtpTransport;
-exports.createSmtpConfig = createSmtpConfig;
+exports.SmtpTransport = SmtpTransport;

package/dist/index.d.cts

@@ -1,6 +1,4 @@
 import { Message, Receipt, Transport, TransportOptions } from "@upyo/core";
-import { Socket } from "node:net";
-import { TLSSocket } from "node:tls";
 
 //#region src/config.d.ts
 
@@ -154,67 +152,6 @@ interface SmtpTlsOptions {
  * This type represents the final configuration after applying defaults,
  * used internally by the SMTP transport implementation.
  */
-type ResolvedSmtpConfig = Omit<Required<SmtpConfig>, "auth" | "tls"> & {
-  readonly auth?: SmtpAuth;
-  readonly tls?: SmtpTlsOptions;
-};
-/**
- * Creates a resolved SMTP configuration by applying default values to optional fields.
- *
- * This function takes a partial SMTP configuration and returns a complete
- * configuration with all optional fields filled with sensible defaults.
- *
- * @param config - The SMTP configuration with optional fields
- * @returns A resolved configuration with all defaults applied
- *
- * @example
- * ```typescript
- * const resolved = createSmtpConfig({
- *   host: 'smtp.example.com',
- *   auth: { user: 'user', pass: 'pass' }
- * });
- *
- * // resolved.port will be 587 (default)
- * // resolved.secure will be true (default)
- * // resolved.poolSize will be 5 (default)
- * ```
- */
-declare function createSmtpConfig(config: SmtpConfig): ResolvedSmtpConfig;
-//#endregion
-//#region src/message-converter.d.ts
-interface SmtpMessage {
-  readonly envelope: SmtpEnvelope;
-  readonly raw: string;
-}
-interface SmtpEnvelope {
-  readonly from: string;
-  readonly to: string[];
-}
-//#endregion
-//#region src/smtp-connection.d.ts
-declare class SmtpConnection {
-  socket: Socket | TLSSocket | null;
-  config: ResolvedSmtpConfig;
-  authenticated: boolean;
-  capabilities: string[];
-  constructor(config: SmtpConfig);
-  connect(signal?: AbortSignal): Promise<void>;
-  sendCommand(command: string, signal?: AbortSignal): Promise<SmtpResponse>;
-  greeting(signal?: AbortSignal): Promise<SmtpResponse>;
-  ehlo(signal?: AbortSignal): Promise<void>;
-  authenticate(signal?: AbortSignal): Promise<void>;
-  private authPlain;
-  authLogin(signal?: AbortSignal): Promise<void>;
-  sendMessage(message: SmtpMessage, signal?: AbortSignal): Promise<string>;
-  extractMessageId(response: string): string;
-  quit(): Promise<void>;
-  reset(signal?: AbortSignal): Promise<void>;
-}
-interface SmtpResponse {
-  readonly code: number;
-  readonly message: string;
-  readonly raw: string;
-}
 //#endregion
 //#region src/smtp-transport.d.ts
 /**
@@ -251,9 +188,15 @@ interface SmtpResponse {
  * ```
  */
 declare class SmtpTransport implements Transport, AsyncDisposable {
+  /**
+   * The SMTP configuration used by this transport.
+   */
   config: SmtpConfig;
-  connectionPool: SmtpConnection[];
+  /**
+   * The maximum number of connections in the pool.
+   */
   poolSize: number;
+  private connectionPool;
   /**
    * Creates a new SMTP transport instance.
    *
@@ -317,10 +260,10 @@ declare class SmtpTransport implements Transport, AsyncDisposable {
    * @returns An async iterable of receipts, one for each message.
    */
   sendMany(messages: Iterable<Message> | AsyncIterable<Message>, options?: TransportOptions): AsyncIterable<Receipt>;
-  getConnection(signal?: AbortSignal): Promise<SmtpConnection>;
-  connectAndSetup(connection: SmtpConnection, signal?: AbortSignal): Promise<void>;
-  returnConnection(connection: SmtpConnection): Promise<void>;
-  discardConnection(connection: SmtpConnection): Promise<void>;
+  private getConnection;
+  private connectAndSetup;
+  private returnConnection;
+  private discardConnection;
   /**
    * Closes all active SMTP connections in the connection pool.
    *
@@ -352,4 +295,4 @@ declare class SmtpTransport implements Transport, AsyncDisposable {
   [Symbol.asyncDispose](): Promise<void>;
 }
 //#endregion
-export { SmtpAuth, SmtpConfig, SmtpTlsOptions, SmtpTransport, createSmtpConfig };
+export { SmtpAuth, SmtpConfig, SmtpTlsOptions, SmtpTransport };

package/dist/index.d.ts

@@ -1,5 +1,3 @@
-import { Socket } from "node:net";
-import { TLSSocket } from "node:tls";
 import { Message, Receipt, Transport, TransportOptions } from "@upyo/core";
 
 //#region src/config.d.ts
@@ -154,67 +152,6 @@ interface SmtpTlsOptions {
  * This type represents the final configuration after applying defaults,
  * used internally by the SMTP transport implementation.
  */
-type ResolvedSmtpConfig = Omit<Required<SmtpConfig>, "auth" | "tls"> & {
-  readonly auth?: SmtpAuth;
-  readonly tls?: SmtpTlsOptions;
-};
-/**
- * Creates a resolved SMTP configuration by applying default values to optional fields.
- *
- * This function takes a partial SMTP configuration and returns a complete
- * configuration with all optional fields filled with sensible defaults.
- *
- * @param config - The SMTP configuration with optional fields
- * @returns A resolved configuration with all defaults applied
- *
- * @example
- * ```typescript
- * const resolved = createSmtpConfig({
- *   host: 'smtp.example.com',
- *   auth: { user: 'user', pass: 'pass' }
- * });
- *
- * // resolved.port will be 587 (default)
- * // resolved.secure will be true (default)
- * // resolved.poolSize will be 5 (default)
- * ```
- */
-declare function createSmtpConfig(config: SmtpConfig): ResolvedSmtpConfig;
-//#endregion
-//#region src/message-converter.d.ts
-interface SmtpMessage {
-  readonly envelope: SmtpEnvelope;
-  readonly raw: string;
-}
-interface SmtpEnvelope {
-  readonly from: string;
-  readonly to: string[];
-}
-//#endregion
-//#region src/smtp-connection.d.ts
-declare class SmtpConnection {
-  socket: Socket | TLSSocket | null;
-  config: ResolvedSmtpConfig;
-  authenticated: boolean;
-  capabilities: string[];
-  constructor(config: SmtpConfig);
-  connect(signal?: AbortSignal): Promise<void>;
-  sendCommand(command: string, signal?: AbortSignal): Promise<SmtpResponse>;
-  greeting(signal?: AbortSignal): Promise<SmtpResponse>;
-  ehlo(signal?: AbortSignal): Promise<void>;
-  authenticate(signal?: AbortSignal): Promise<void>;
-  private authPlain;
-  authLogin(signal?: AbortSignal): Promise<void>;
-  sendMessage(message: SmtpMessage, signal?: AbortSignal): Promise<string>;
-  extractMessageId(response: string): string;
-  quit(): Promise<void>;
-  reset(signal?: AbortSignal): Promise<void>;
-}
-interface SmtpResponse {
-  readonly code: number;
-  readonly message: string;
-  readonly raw: string;
-}
 //#endregion
 //#region src/smtp-transport.d.ts
 /**
@@ -251,9 +188,15 @@ interface SmtpResponse {
  * ```
  */
 declare class SmtpTransport implements Transport, AsyncDisposable {
+  /**
+   * The SMTP configuration used by this transport.
+   */
   config: SmtpConfig;
-  connectionPool: SmtpConnection[];
+  /**
+   * The maximum number of connections in the pool.
+   */
   poolSize: number;
+  private connectionPool;
   /**
    * Creates a new SMTP transport instance.
    *
@@ -317,10 +260,10 @@ declare class SmtpTransport implements Transport, AsyncDisposable {
    * @returns An async iterable of receipts, one for each message.
    */
   sendMany(messages: Iterable<Message> | AsyncIterable<Message>, options?: TransportOptions): AsyncIterable<Receipt>;
-  getConnection(signal?: AbortSignal): Promise<SmtpConnection>;
-  connectAndSetup(connection: SmtpConnection, signal?: AbortSignal): Promise<void>;
-  returnConnection(connection: SmtpConnection): Promise<void>;
-  discardConnection(connection: SmtpConnection): Promise<void>;
+  private getConnection;
+  private connectAndSetup;
+  private returnConnection;
+  private discardConnection;
   /**
    * Closes all active SMTP connections in the connection pool.
    *
@@ -352,4 +295,4 @@ declare class SmtpTransport implements Transport, AsyncDisposable {
   [Symbol.asyncDispose](): Promise<void>;
 }
 //#endregion
-export { SmtpAuth, SmtpConfig, SmtpTlsOptions, SmtpTransport, createSmtpConfig };
+export { SmtpAuth, SmtpConfig, SmtpTlsOptions, SmtpTransport };

package/dist/index.js

@@ -8,21 +8,11 @@ import { formatAddress } from "@upyo/core";
 *
 * This function takes a partial SMTP configuration and returns a complete
 * configuration with all optional fields filled with sensible defaults.
+* It is used internally by the SMTP transport.
 *
 * @param config - The SMTP configuration with optional fields
 * @returns A resolved configuration with all defaults applied
-*
-* @example
-* ```typescript
-* const resolved = createSmtpConfig({
-*   host: 'smtp.example.com',
-*   auth: { user: 'user', pass: 'pass' }
-* });
-*
-* // resolved.port will be 587 (default)
-* // resolved.secure will be true (default)
-* // resolved.poolSize will be 5 (default)
-* ```
+* @internal
 */
 function createSmtpConfig(config) {
 	return {
@@ -243,7 +233,7 @@ var SmtpConnection = class {
 
 //#endregion
 //#region src/message-converter.ts
-function convertMessage(message) {
+async function convertMessage(message) {
 	const envelope = {
 		from: message.sender.address,
 		to: [
@@ -252,23 +242,23 @@ function convertMessage(message) {
 			...message.bccRecipients.map((r) => r.address)
 		]
 	};
-	const raw = buildRawMessage(message);
+	const raw = await buildRawMessage(message);
 	return {
 		envelope,
 		raw
 	};
 }
-function buildRawMessage(message) {
+async function buildRawMessage(message) {
 	const lines = [];
 	const boundary = generateBoundary();
 	const hasAttachments = message.attachments.length > 0;
 	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()}>`);
@@ -323,7 +313,7 @@ function buildRawMessage(message) {
 				lines.push(`Content-ID: <${attachment.contentId}>`);
 			} else lines.push(`Content-Disposition: attachment; filename="${attachment.filename}"`);
 			lines.push("");
-			lines.push(encodeBase64(attachment.content));
+			lines.push(encodeBase64(await attachment.content));
 		}
 		lines.push("");
 		lines.push(`--${boundary}--`);
@@ -352,17 +342,48 @@ function encodeHeaderValue(value) {
 	if (!/^[\x20-\x7E]*$/.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));
@@ -405,9 +426,15 @@ function encodeBase64(data) {
 * ```
 */
 var SmtpTransport = class {
+	/**
+	* The SMTP configuration used by this transport.
+	*/
 	config;
-	connectionPool = [];
+	/**
+	* The maximum number of connections in the pool.
+	*/
 	poolSize;
+	connectionPool = [];
 	/**
 	* Creates a new SMTP transport instance.
 	*
@@ -449,21 +476,19 @@ var SmtpTransport = class {
 		const connection = await this.getConnection(options?.signal);
 		try {
 			options?.signal?.throwIfAborted();
-			const smtpMessage = convertMessage(message);
+			const smtpMessage = await convertMessage(message);
 			options?.signal?.throwIfAborted();
 			const messageId = await connection.sendMessage(smtpMessage, options?.signal);
 			await this.returnConnection(connection);
 			return {
-				messageId,
-				errorMessages: [],
-				successful: true
+				successful: true,
+				messageId
 			};
 		} catch (error) {
 			await this.discardConnection(connection);
 			return {
-				messageId: "",
-				errorMessages: [error instanceof Error ? error.message : String(error)],
-				successful: false
+				successful: false,
+				errorMessages: [error instanceof Error ? error.message : String(error)]
 			};
 		}
 	}
@@ -505,27 +530,24 @@ var SmtpTransport = class {
 				options?.signal?.throwIfAborted();
 				if (!connectionValid) {
 					yield {
-						messageId: "",
-						errorMessages: ["Connection is no longer valid"],
-						successful: false
+						successful: false,
+						errorMessages: ["Connection is no longer valid"]
 					};
 					continue;
 				}
 				try {
-					const smtpMessage = convertMessage(message);
+					const smtpMessage = await convertMessage(message);
 					options?.signal?.throwIfAborted();
 					const messageId = await connection.sendMessage(smtpMessage, options?.signal);
 					yield {
-						messageId,
-						errorMessages: [],
-						successful: true
+						successful: true,
+						messageId
 					};
 				} catch (error) {
 					connectionValid = false;
 					yield {
-						messageId: "",
-						errorMessages: [error instanceof Error ? error.message : String(error)],
-						successful: false
+						successful: false,
+						errorMessages: [error instanceof Error ? error.message : String(error)]
 					};
 				}
 			}
@@ -533,27 +555,24 @@ var SmtpTransport = class {
 				options?.signal?.throwIfAborted();
 				if (!connectionValid) {
 					yield {
-						messageId: "",
-						errorMessages: ["Connection is no longer valid"],
-						successful: false
+						successful: false,
+						errorMessages: ["Connection is no longer valid"]
 					};
 					continue;
 				}
 				try {
-					const smtpMessage = convertMessage(message);
+					const smtpMessage = await convertMessage(message);
 					options?.signal?.throwIfAborted();
 					const messageId = await connection.sendMessage(smtpMessage, options?.signal);
 					yield {
-						messageId,
-						errorMessages: [],
-						successful: true
+						successful: true,
+						messageId
 					};
 				} catch (error) {
 					connectionValid = false;
 					yield {
-						messageId: "",
-						errorMessages: [error instanceof Error ? error.message : String(error)],
-						successful: false
+						successful: false,
+						errorMessages: [error instanceof Error ? error.message : String(error)]
 					};
 				}
 			}
@@ -638,4 +657,4 @@ var SmtpTransport = class {
 };
 
 //#endregion
-export { SmtpTransport, createSmtpConfig };
+export { SmtpTransport };

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@upyo/smtp",
-  "version": "0.1.0-dev.9+a57dde18",
+  "version": "0.1.1",
   "description": "SMTP transport for Upyo email library",
   "keywords": [
     "email",
@@ -53,12 +53,12 @@
   },
   "sideEffects": false,
   "peerDependencies": {
-    "@upyo/core": "0.1.0-dev.9+a57dde18"
+    "@upyo/core": "0.1.1"
   },
   "devDependencies": {
     "@dotenvx/dotenvx": "^1.47.3",
     "tsdown": "^0.12.7",
-    "typescript": "^5.8.3"
+    "typescript": "5.8.3"
   },
   "scripts": {
     "build": "tsdown",