diff --git a/src/core/utils/auth.ts b/src/core/utils/auth.ts
index 1a4c9332..8bbc9378 100644
--- a/src/core/utils/auth.ts
+++ b/src/core/utils/auth.ts
@@ -49,3 +49,70 @@ export function extractPostLoginRedirectUri(protocol?: string, host?: string, pa
 
   return undefined;
 }
+
+const IV_LENGTH = 16; // For AES, this is always 16
+const CIPHER_ALGORITHM = "aes-256-cbc";
+
+const ENCRYPTION_KEY = process.env.ENCRYPTION_KEY || crypto.randomBytes(16).toString("hex");
+
+const SIGNING_KEY = process.env.SIGNING_KEY || crypto.randomBytes(16).toString("hex");
+const bitLength = SIGNING_KEY.length * 8;
+const HMAC_ALGORITHM = bitLength <= 256 ? "sha256" : bitLength <= 384 ? "sha384" : "sha512";
+
+export function encryptAndSign(value: string): string | undefined {
+  try {
+    // encrypt
+    const iv = crypto.randomBytes(IV_LENGTH);
+    const cipher = crypto.createCipheriv(CIPHER_ALGORITHM, Buffer.from(ENCRYPTION_KEY), iv);
+    let encrypted = cipher.update(value);
+    encrypted = Buffer.concat([encrypted, cipher.final()]);
+    const encryptedValue = iv.toString("hex") + ":" + encrypted.toString("hex");
+
+    // sign
+    const hash = crypto.createHmac(HMAC_ALGORITHM, process.env.SALT || "");
+    hash.update(encryptedValue);
+    const signature = hash.digest("hex");
+
+    const signedEncryptedValue = signature + ":" + encryptedValue;
+    return signedEncryptedValue;
+  } catch {
+    return undefined;
+  }
+}
+
+export function validateSignatureAndDecrypt(data: string): string | undefined {
+  try {
+    const dataSegments: string[] = data.includes(":") ? data.split(":") : [];
+
+    if (dataSegments.length < 3) {
+      return undefined;
+    }
+
+    // validate signature
+    const signature = dataSegments.shift() || "";
+    const signedData = dataSegments.join(":");
+
+    const hash = crypto.createHmac(HMAC_ALGORITHM, process.env.SALT || "");
+    hash.update(signedData);
+    const testSignature = hash.digest("hex");
+
+    if (signature !== testSignature) {
+      return undefined;
+    }
+
+    // decrypt
+    const iv = Buffer.from(dataSegments.shift() || "", "hex");
+    const encryptedText = Buffer.from(dataSegments.join(":"), "hex");
+    const decipher = crypto.createDecipheriv(CIPHER_ALGORITHM, Buffer.from(ENCRYPTION_KEY), iv);
+    let decrypted = decipher.update(encryptedText);
+    decrypted = Buffer.concat([decrypted, decipher.final()]);
+    return decrypted.toString();
+  } catch {
+    return undefined;
+  }
+}
+
+export function isValueEncryptedAndSigned(value: string) {
+  const segments = value.split(":");
+  return segments.length === 3 && segments[0].length === 64 && segments[1].length >= 32;
+}
diff --git a/src/core/utils/cookie.ts b/src/core/utils/cookie.ts
index 900eae0d..6fd05321 100644
--- a/src/core/utils/cookie.ts
+++ b/src/core/utils/cookie.ts
@@ -1,22 +1,9 @@
 import chalk from "chalk";
 import cookie from "cookie";
 import { SWA_AUTH_CONTEXT_COOKIE, SWA_AUTH_COOKIE } from "../constants";
+import { isValueEncryptedAndSigned, validateSignatureAndDecrypt } from "./auth";
 import { logger } from "./logger";
 
-/**
- * Check if the StaticWebAppsAuthCookie is available.
- * @param cookieValue The cookie value.
- * @returns True if StaticWebAppsAuthCookie is found. False otherwise.
- */
-export function validateCookie(cookieValue: string | number | string[]) {
-  if (typeof cookieValue !== "string") {
-    throw Error(`TypeError: cookie value must be a string`);
-  }
-
-  const cookies = cookie.parse(cookieValue);
-  return !!cookies[SWA_AUTH_COOKIE];
-}
-
 /**
  * Serialize a cookie name-value pair into a string that can be used in Set-Cookie header.
  * @param cookieName The name for the cookie.
@@ -29,21 +16,23 @@ export function serializeCookie(cookieName: string, cookieValue: string, options
   return cookie.serialize(cookieName, cookieValue, options);
 }
 
+/**
+ * Check if the StaticWebAppsAuthCookie is available.
+ * @param cookieValue The cookie value.
+ * @returns True if StaticWebAppsAuthCookie is found. False otherwise.
+ */
+export function validateCookie(cookieValue: string | number | string[]) {
+  return validateCookieByName(SWA_AUTH_COOKIE, cookieValue);
+}
+
 /**
  *
  * @param cookieValue
  * @returns A ClientPrincipal object.
  */
 export function decodeCookie(cookieValue: string): ClientPrincipal | null {
-  logger.silly(`decoding StaticWebAppsAuthCookie cookie`);
-  const cookies = cookie.parse(cookieValue);
-  if (cookies[SWA_AUTH_COOKIE]) {
-    const decodedValue = Buffer.from(cookies[SWA_AUTH_COOKIE], "base64").toString();
-    logger.silly(` - StaticWebAppsAuthCookie: ${chalk.yellow(decodedValue)}`);
-    return JSON.parse(decodedValue);
-  }
-  logger.silly(` - no cookie 'StaticWebAppsAuthCookie' found`);
-  return null;
+  const stringValue = decodeCookieByName(SWA_AUTH_COOKIE, cookieValue);
+  return stringValue ? JSON.parse(stringValue) : null;
 }
 
 /**
@@ -52,12 +41,7 @@ export function decodeCookie(cookieValue: string): ClientPrincipal | null {
  * @returns True if StaticWebAppsAuthContextCookie is found. False otherwise.
  */
 export function validateAuthContextCookie(cookieValue: string | number | string[]) {
-  if (typeof cookieValue !== "string") {
-    throw Error(`TypeError: cookie value must be a string`);
-  }
-
-  const cookies = cookie.parse(cookieValue);
-  return !!cookies[SWA_AUTH_CONTEXT_COOKIE];
+  return validateCookieByName(SWA_AUTH_CONTEXT_COOKIE, cookieValue);
 }
 
 /**
@@ -66,13 +50,176 @@ export function validateAuthContextCookie(cookieValue: string | number | string[
  * @returns StaticWebAppsAuthContextCookie string.
  */
 export function decodeAuthContextCookie(cookieValue: string): AuthContext | null {
-  logger.silly(`decoding StaticWebAppsAuthContextCookie cookie`);
-  const cookies = cookie.parse(cookieValue);
-  if (cookies[SWA_AUTH_CONTEXT_COOKIE]) {
-    const decodedValue = Buffer.from(cookies[SWA_AUTH_CONTEXT_COOKIE], "base64").toString();
-    logger.silly(` - StaticWebAppsAuthContextCookie: ${chalk.yellow(decodedValue)}`);
-    return JSON.parse(decodedValue);
+  const stringValue = decodeCookieByName(SWA_AUTH_CONTEXT_COOKIE, cookieValue);
+  return stringValue ? JSON.parse(stringValue) : null;
+}
+
+// local functions
+function getCookie(cookieName: string, cookies: Record<string, string>) {
+  const nonChunkedCookie = cookies[cookieName];
+
+  if (nonChunkedCookie) {
+    // prefer the non-chunked cookie if it exists
+    return nonChunkedCookie;
   }
-  logger.silly(` - no cookie 'StaticWebAppsAuthContextCookie' found`);
+
+  let chunkedCookie = "";
+  let chunk = "";
+  let index = 0;
+
+  do {
+    chunkedCookie = `${chunkedCookie}${chunk}`;
+    chunk = cookies[`${cookieName}_${index}`];
+    index += 1;
+  } while (chunk);
+
+  return chunkedCookie;
+}
+
+function validateCookieByName(cookieName: string, cookieValue: string | number | string[]) {
+  if (typeof cookieValue !== "string") {
+    throw Error(`TypeError: cookie value must be a string`);
+  }
+
+  const cookies = cookie.parse(cookieValue);
+  return !!getCookie(cookieName, cookies);
+}
+
+function decodeCookieByName(cookieName: string, cookieValue: string) {
+  logger.silly(`decoding ${cookieName} cookie`);
+  const cookies = cookie.parse(cookieValue);
+
+  const value = getCookie(cookieName, cookies);
+
+  if (value) {
+    const decodedValue = Buffer.from(value, "base64").toString();
+    logger.silly(` - ${cookieName} decoded: ${chalk.yellow(decodedValue)}`);
+
+    if (!decodedValue) {
+      logger.silly(` - failed to decode '${cookieName}'`);
+      return null;
+    }
+
+    if (isValueEncryptedAndSigned(decodedValue)) {
+      const decryptedValue = validateSignatureAndDecrypt(decodedValue);
+      logger.silly(` - ${cookieName} decrypted: ${chalk.yellow(decryptedValue)}`);
+
+      if (!decryptedValue) {
+        logger.silly(` - failed to validate and decrypt '${cookieName}'`);
+        return null;
+      }
+
+      return decryptedValue;
+    }
+
+    return decodedValue;
+  }
+  logger.silly(` - no cookie '${cookieName}' found`);
   return null;
 }
+
+export interface CookieOptions extends Omit<cookie.CookieSerializeOptions, "expires"> {
+  name: string;
+  value: string;
+  expires?: string;
+}
+
+export class CookiesManager {
+  private readonly _chunkSize = 2000;
+  private readonly _existingCookies: Record<string, string>;
+  private _cookiesToSet: Record<string, CookieOptions> = {};
+  private _cookiesToDelete: Record<string, string> = {};
+
+  constructor(requestCookie?: string) {
+    this._existingCookies = requestCookie ? cookie.parse(requestCookie) : {};
+  }
+
+  private _generateDeleteChunks(name: string, force: boolean /* add the delete cookie even if the corresponding cookie doesn't exist */) {
+    const cookies: Record<string, CookieOptions> = {};
+
+    // check for unchunked cookie
+    if (force || this._existingCookies[name]) {
+      cookies[name] = {
+        name: name,
+        value: "deleted",
+        path: "/",
+        httpOnly: false,
+        expires: new Date(1).toUTCString(),
+      };
+    }
+
+    // check for chunked cookie
+    let found = true;
+    let index = 0;
+
+    while (found) {
+      const chunkName = `${name}_${index}`;
+      found = !!this._existingCookies[chunkName];
+      if (found) {
+        cookies[chunkName] = {
+          name: chunkName,
+          value: "deleted",
+          path: "/",
+          httpOnly: false,
+          expires: new Date(1).toUTCString(),
+        };
+      }
+      index += 1;
+    }
+
+    return cookies;
+  }
+
+  private _generateChunks(options: CookieOptions): CookieOptions[] {
+    const { name, value } = options;
+
+    // pre-populate with cookies for deleting existing chunks
+    const cookies: Record<string, CookieOptions> = this._generateDeleteChunks(options.name, false);
+
+    // generate chunks
+    if (value !== "deleted") {
+      const chunkCount = Math.ceil(value.length / this._chunkSize);
+
+      let index = 0;
+      let chunkName = "";
+
+      while (index < chunkCount) {
+        const position = index * this._chunkSize;
+        const chunk = value.substring(position, position + this._chunkSize);
+
+        chunkName = `${name}_${index}`;
+
+        cookies[chunkName] = {
+          ...options,
+          name: chunkName,
+          value: chunk,
+        };
+
+        index += 1;
+      }
+    }
+
+    return Object.values(cookies);
+  }
+
+  public addCookieToSet(options: CookieOptions): void {
+    this._cookiesToSet[options.name.toLowerCase()] = options;
+  }
+
+  public addCookieToDelete(name: string): void {
+    this._cookiesToDelete[name.toLowerCase()] = name;
+  }
+
+  public getCookies(): CookieOptions[] {
+    const allCookies: CookieOptions[] = [];
+    Object.values(this._cookiesToDelete).forEach((cookieName) => {
+      const chunks = this._generateDeleteChunks(cookieName, true);
+      allCookies.push(...Object.values(chunks));
+    });
+    Object.values(this._cookiesToSet).forEach((cookie) => {
+      const chunks = this._generateChunks(cookie);
+      allCookies.push(...chunks);
+    });
+    return allCookies;
+  }
+}
diff --git a/src/msha/auth/routes/auth-login-provider-callback.ts b/src/msha/auth/routes/auth-login-provider-callback.ts
index c011ebd2..ffbb681b 100644
--- a/src/msha/auth/routes/auth-login-provider-callback.ts
+++ b/src/msha/auth/routes/auth-login-provider-callback.ts
@@ -1,10 +1,10 @@
-import { decodeAuthContextCookie, parseUrl, response, validateAuthContextCookie } from "../../../core";
+import { CookiesManager, decodeAuthContextCookie, parseUrl, response, validateAuthContextCookie } from "../../../core";
 import * as http from "http";
 import * as https from "https";
 import * as querystring from "querystring";
 import { SWA_CLI_API_URI, SWA_CLI_APP_PROTOCOL } from "../../../core/constants";
 import { DEFAULT_CONFIG } from "../../../config";
-import { hashStateGuid, isNonceExpired } from "../../../core/utils/auth";
+import { encryptAndSign, hashStateGuid, isNonceExpired } from "../../../core/utils/auth";
 
 const getGithubAuthToken = function (codeValue: string, clientId: string, clientSecret: string) {
   const data = querystring.stringify({
@@ -469,27 +469,27 @@ const httpTrigger = async function (context: Context, request: http.IncomingMess
     } catch {}
   }
 
+  const authCookieString = clientPrincipal && JSON.stringify(clientPrincipal);
+  const authCookieEncrypted = authCookieString && encryptAndSign(authCookieString);
+  const authCookie = authCookieEncrypted ? btoa(authCookieEncrypted) : undefined;
+
+  const cookiesManager = new CookiesManager(request.headers.cookie);
+  cookiesManager.addCookieToDelete("StaticWebAppsAuthContextCookie");
+  if (authCookie) {
+    cookiesManager.addCookieToSet({
+      name: "StaticWebAppsAuthCookie",
+      value: authCookie,
+      domain: DEFAULT_CONFIG.host,
+      path: "/",
+      secure: true,
+      httpOnly: true,
+      expires: new Date(Date.now() + 1000 * 60 * 60 * 8).toUTCString(),
+    });
+  }
+
   context.res = response({
     context,
-    cookies: [
-      {
-        name: "StaticWebAppsAuthContextCookie",
-        value: "deleted",
-        path: "/",
-        secure: true,
-        httpOnly: true,
-        expires: new Date(1).toUTCString(),
-      },
-      {
-        name: "StaticWebAppsAuthCookie",
-        value: clientPrincipal === null ? "deleted" : btoa(JSON.stringify(clientPrincipal)),
-        domain: DEFAULT_CONFIG.host,
-        path: "/",
-        secure: true,
-        httpOnly: true,
-        expires: clientPrincipal === null ? new Date(1).toUTCString() : new Date(Date.now() + 1000 * 60 * 60 * 8).toUTCString(),
-      },
-    ],
+    cookies: cookiesManager.getCookies(),
     status: 302,
     headers: {
       status: 302,
diff --git a/src/msha/auth/routes/auth-login-provider-custom.ts b/src/msha/auth/routes/auth-login-provider-custom.ts
index 45e233d9..fb7636f2 100644
--- a/src/msha/auth/routes/auth-login-provider-custom.ts
+++ b/src/msha/auth/routes/auth-login-provider-custom.ts
@@ -1,8 +1,8 @@
-import { response } from "../../../core";
+import { CookiesManager, response } from "../../../core";
 import * as http from "http";
 import { SWA_CLI_APP_PROTOCOL } from "../../../core/constants";
 import { DEFAULT_CONFIG } from "../../../config";
-import { extractPostLoginRedirectUri, hashStateGuid, newNonceWithExpiration } from "../../../core/utils/auth";
+import { encryptAndSign, extractPostLoginRedirectUri, hashStateGuid, newNonceWithExpiration } from "../../../core/utils/auth";
 
 const httpTrigger = async function (context: Context, request: http.IncomingMessage, customAuth?: SWAConfigFileAuth) {
   await Promise.resolve();
@@ -50,6 +50,10 @@ const httpTrigger = async function (context: Context, request: http.IncomingMess
     postLoginRedirectUri: extractPostLoginRedirectUri(SWA_CLI_APP_PROTOCOL, request.headers.host, request.url),
   };
 
+  const authContextCookieString = JSON.stringify(authContext);
+  const authContextCookieEncrypted = encryptAndSign(authContextCookieString);
+  const authContextCookie = authContextCookieEncrypted ? btoa(authContextCookieEncrypted) : undefined;
+
   const hashedState = hashStateGuid(state);
   const redirectUri = `${SWA_CLI_APP_PROTOCOL}://${DEFAULT_CONFIG.host}:${DEFAULT_CONFIG.port}`;
 
@@ -58,18 +62,23 @@ const httpTrigger = async function (context: Context, request: http.IncomingMess
       ? `https://accounts.google.com/o/oauth2/v2/auth?response_type=code&client_id=${clientId}&redirect_uri=${redirectUri}/.auth/login/google/callback&scope=openid+profile+email&state=${hashedState}`
       : `https://github.com/login/oauth/authorize?response_type=code&client_id=${clientId}&redirect_uri=${redirectUri}/.auth/login/github/callback&scope=read:user&state=${hashedState}`;
 
+  const cookiesManager = new CookiesManager(request.headers.cookie);
+  if (!authContextCookie) {
+    cookiesManager.addCookieToDelete("StaticWebAppsAuthContextCookie");
+  } else {
+    cookiesManager.addCookieToSet({
+      name: "StaticWebAppsAuthContextCookie",
+      value: authContextCookie,
+      domain: DEFAULT_CONFIG.host,
+      path: "/",
+      secure: true,
+      httpOnly: true,
+    });
+  }
+
   context.res = response({
     context,
-    cookies: [
-      {
-        name: "StaticWebAppsAuthContextCookie",
-        value: btoa(JSON.stringify(authContext)),
-        domain: DEFAULT_CONFIG.host,
-        path: "/",
-        secure: true,
-        httpOnly: true,
-      },
-    ],
+    cookies: cookiesManager.getCookies(),
     status: 302,
     headers: {
       status: 302,
diff --git a/src/msha/auth/routes/auth-login-provider.ts b/src/msha/auth/routes/auth-login-provider.ts
index 4e0d973c..36f7c973 100644
--- a/src/msha/auth/routes/auth-login-provider.ts
+++ b/src/msha/auth/routes/auth-login-provider.ts
@@ -1,11 +1,15 @@
 import { IncomingMessage } from "http";
-import { response } from "../../../core";
+import { CookiesManager, response } from "../../../core";
 
 const fs = require("fs").promises;
 const path = require("path");
 
 const httpTrigger = async function (context: Context, request: IncomingMessage) {
   const body = await fs.readFile(path.join(__dirname, "..", "..", "..", "public", "auth.html"), "utf-8");
+
+  const cookiesManager = new CookiesManager(request.headers.cookie);
+  cookiesManager.addCookieToDelete("StaticWebAppsAuthContextCookie");
+
   context.res = response({
     context,
     status: 200,
diff --git a/src/msha/auth/routes/auth-logout-https.spec.ts b/src/msha/auth/routes/auth-logout-https.spec.ts
index 60055f71..0159bbbc 100644
--- a/src/msha/auth/routes/auth-logout-https.spec.ts
+++ b/src/msha/auth/routes/auth-logout-https.spec.ts
@@ -14,7 +14,7 @@ describe("auth-logout-https", () => {
     name: "StaticWebAppsAuthCookie",
     value: "deleted",
     path: "/",
-    HttpOnly: false,
+    httpOnly: false,
     expires: new Date(1).toUTCString(),
   };
 
diff --git a/src/msha/auth/routes/auth-logout.spec.ts b/src/msha/auth/routes/auth-logout.spec.ts
index 602325d8..4b0cf8a4 100644
--- a/src/msha/auth/routes/auth-logout.spec.ts
+++ b/src/msha/auth/routes/auth-logout.spec.ts
@@ -14,7 +14,7 @@ describe("auth_logout", () => {
     name: "StaticWebAppsAuthCookie",
     value: "deleted",
     path: "/",
-    HttpOnly: false,
+    httpOnly: false,
     expires: new Date(1).toUTCString(),
   };
 
diff --git a/src/msha/auth/routes/auth-logout.ts b/src/msha/auth/routes/auth-logout.ts
index 27d36b01..bf67d9de 100644
--- a/src/msha/auth/routes/auth-logout.ts
+++ b/src/msha/auth/routes/auth-logout.ts
@@ -1,5 +1,6 @@
 import type http from "http";
-import { response } from "../../../core";
+import { CookiesManager, response } from "../../../core";
+// import { response } from "../../../core";
 import { SWA_CLI_APP_PROTOCOL } from "../../../core/constants";
 
 export default async function (context: Context, req: http.IncomingMessage) {
@@ -17,18 +18,13 @@ export default async function (context: Context, req: http.IncomingMessage) {
   const query = new URL(req?.url || "", uri).searchParams;
   const location = `${uri}${query.get("post_logout_redirect_uri") || "/"}`;
 
+  const cookiesManager = new CookiesManager(req.headers.cookie);
+  cookiesManager.addCookieToDelete("StaticWebAppsAuthCookie");
+
   context.res = response({
     context,
     status: 302,
-    cookies: [
-      {
-        name: "StaticWebAppsAuthCookie",
-        value: "deleted",
-        path: "/",
-        HttpOnly: false,
-        expires: new Date(1).toUTCString(),
-      },
-    ],
+    cookies: cookiesManager.getCookies(),
     headers: {
       Location: location,
     },