diff --git a/bin/cli-flags.js b/bin/cli-flags.js
index 1f1376ef75..ab968c5730 100644
--- a/bin/cli-flags.js
+++ b/bin/cli-flags.js
@@ -121,6 +121,21 @@ module.exports = {
     simpleType: "boolean",
     multiple: false,
   },
+  "client-overlay-trusted-types-policy-name": {
+    configs: [
+      {
+        description:
+          "The name of a Trusted Types policy for the overlay. Defaults to 'webpack-dev-server#overlay'.",
+        multiple: false,
+        path: "client.overlay.trustedTypesPolicyName",
+        type: "string",
+      },
+    ],
+    description:
+      "The name of a Trusted Types policy for the overlay. Defaults to 'webpack-dev-server#overlay'.",
+    multiple: false,
+    simpleType: "string",
+  },
   "client-overlay-warnings": {
     configs: [
       {
diff --git a/test/cli/__snapshots__/http2-option.test.js.snap.webpack5 b/test/cli/__snapshots__/http2-option.test.js.snap.webpack5
index ec162308f6..02e048a58d 100644
--- a/test/cli/__snapshots__/http2-option.test.js.snap.webpack5
+++ b/test/cli/__snapshots__/http2-option.test.js.snap.webpack5
@@ -1,7 +1,8 @@
 // Jest Snapshot v1, https://goo.gl/fbAQLP
 
 exports[`"http2" CLI option should work using "--http2" 1`] = `
-"<i> [webpack-dev-server] SSL certificate: <cwd>/node_modules/.cache/webpack-dev-server/server.pem
+"<i> [webpack-dev-server] Generating SSL certificate...
+<i> [webpack-dev-server] SSL certificate: <cwd>/node_modules/.cache/webpack-dev-server/server.pem
 <i> [webpack-dev-server] Project is running at:
 <i> Loopback: https://localhost:<port>/, https://<ip-v4>:<port>/, https://[<ip-v6>]:<port>/
 <i> [webpack-dev-server] On Your Network (IPv4): https://<ip-v4>:<port>/
diff --git a/test/cli/__snapshots__/https-option.test.js.snap.webpack5 b/test/cli/__snapshots__/https-option.test.js.snap.webpack5
index 759d9931f7..e50636d389 100644
--- a/test/cli/__snapshots__/https-option.test.js.snap.webpack5
+++ b/test/cli/__snapshots__/https-option.test.js.snap.webpack5
@@ -10,7 +10,8 @@ exports[`"https" CLI option should warn using "--https-cacert" and "--https-ca"
 `;
 
 exports[`"https" CLI option should work using "--https" 1`] = `
-"<i> [webpack-dev-server] SSL certificate: <cwd>/node_modules/.cache/webpack-dev-server/server.pem
+"<i> [webpack-dev-server] Generating SSL certificate...
+<i> [webpack-dev-server] SSL certificate: <cwd>/node_modules/.cache/webpack-dev-server/server.pem
 <i> [webpack-dev-server] Project is running at:
 <i> Loopback: https://localhost:<port>/, https://<ip-v4>:<port>/, https://[<ip-v6>]:<port>/
 <i> [webpack-dev-server] On Your Network (IPv4): https://<ip-v4>:<port>/
diff --git a/test/e2e/__snapshots__/hot-and-live-reload.test.js.snap.webpack5 b/test/e2e/__snapshots__/hot-and-live-reload.test.js.snap.webpack5
index 87715569f4..1f46bebeb3 100644
--- a/test/e2e/__snapshots__/hot-and-live-reload.test.js.snap.webpack5
+++ b/test/e2e/__snapshots__/hot-and-live-reload.test.js.snap.webpack5
@@ -54,7 +54,6 @@ exports[`hot and live reload should work and allow to disable live reload using
 Array [
   "[webpack-dev-server] Live Reloading enabled.",
   "[webpack-dev-server] App updated. Recompiling...",
-  "[webpack-dev-server] App updated. Recompiling...",
 ]
 `;
 
@@ -267,6 +266,8 @@ Array [
   "[webpack-dev-server] App updated. Recompiling...",
   "[webpack-dev-server] App hot update...",
   "[HMR] Checking for updates on the server...",
+  "[webpack-dev-server] App updated. Recompiling...",
+  "[webpack-dev-server] Nothing changed.",
   "[HMR] Updated modules:",
   "[HMR]  - ./main.css",
   "[HMR]  - ../../../node_modules/css-loader/dist/cjs.js!./main.css",
diff --git a/test/e2e/__snapshots__/overlay.test.js.snap.webpack5 b/test/e2e/__snapshots__/overlay.test.js.snap.webpack5
index c8a56d4012..7c4fdc318b 100644
--- a/test/e2e/__snapshots__/overlay.test.js.snap.webpack5
+++ b/test/e2e/__snapshots__/overlay.test.js.snap.webpack5
@@ -364,6 +364,14 @@ exports[`overlay should not show initially, then show on an error, then show oth
 "
 `;
 
+exports[`overlay should not show overlay when Trusted Types are enabled, but policy is not allowed: page html 1`] = `
+"<body>
+  <h1>webpack-dev-server is running...</h1>
+  <script type=\\"text/javascript\\" charset=\\"utf-8\\" src=\\"/main.js\\"></script>
+</body>
+"
+`;
+
 exports[`overlay should show a warning after invalidation: overlay html 1`] = `
 "<body>
   <div
@@ -1319,3 +1327,68 @@ exports[`overlay should show an error when "client.overlay.warnings" is "true":
 </body>
 "
 `;
+
+exports[`overlay should show overlay when Trusted Types are enabled: overlay html 1`] = `
+"<body>
+  <div
+    id=\\"webpack-dev-server-client-overlay-div\\"
+    style=\\"
+      position: fixed;
+      box-sizing: border-box;
+      inset: 0px;
+      width: 100vw;
+      height: 100vh;
+      background-color: rgba(0, 0, 0, 0.85);
+      color: rgb(232, 232, 232);
+      font-family: Menlo, Consolas, monospace;
+      font-size: large;
+      padding: 2rem;
+      line-height: 1.2;
+      white-space: pre-wrap;
+      overflow: auto;
+    \\"
+  >
+    <span>Compiled with problems:</span
+    ><button
+      style=\\"
+        background: transparent;
+        border: none;
+        font-size: 20px;
+        font-weight: bold;
+        color: white;
+        cursor: pointer;
+        float: right;
+      \\"
+    >
+      X</button
+    ><br /><br />
+    <div>
+      <span style=\\"color: rgb(227, 96, 73)\\">ERROR</span><br /><br />
+      <div>Error from compilation. Can't find 'test' module.</div>
+      <br /><br />
+    </div>
+  </div>
+</body>
+"
+`;
+
+exports[`overlay should show overlay when Trusted Types are enabled: page html 1`] = `
+"<body>
+  <h1>webpack-dev-server is running...</h1>
+  <script type=\\"text/javascript\\" charset=\\"utf-8\\" src=\\"/main.js\\"></script>
+
+  <iframe
+    id=\\"webpack-dev-server-client-overlay\\"
+    src=\\"about:blank\\"
+    style=\\"
+      position: fixed;
+      inset: 0px;
+      width: 100vw;
+      height: 100vh;
+      border: none;
+      z-index: 2147483647;
+    \\"
+  ></iframe>
+</body>
+"
+`;
diff --git a/test/fixtures/static-config/public/node_modules/index.html b/test/fixtures/static-config/public/node_modules/index.html
new file mode 100644
index 0000000000..ba0e162e1c
--- /dev/null
+++ b/test/fixtures/static-config/public/node_modules/index.html
@@ -0,0 +1 @@
+bar
\ No newline at end of file
diff --git a/types/bin/cli-flags.d.ts b/types/bin/cli-flags.d.ts
index fa98132496..ac17b73866 100644
--- a/types/bin/cli-flags.d.ts
+++ b/types/bin/cli-flags.d.ts
@@ -91,6 +91,17 @@ declare const _exports: {
     simpleType: string;
     multiple: boolean;
   };
+  "client-overlay-trusted-types-policy-name": {
+    configs: {
+      description: string;
+      multiple: boolean;
+      path: string;
+      type: string;
+    }[];
+    description: string;
+    multiple: boolean;
+    simpleType: string;
+  };
   "client-overlay-warnings": {
     configs: {
       type: string;
diff --git a/types/lib/Server.d.ts b/types/lib/Server.d.ts
index 672b7b5413..74cb035570 100644
--- a/types/lib/Server.d.ts
+++ b/types/lib/Server.d.ts
@@ -393,6 +393,17 @@ declare class Server {
         simpleType: string;
         multiple: boolean;
       };
+      "client-overlay-trusted-types-policy-name": {
+        configs: {
+          description: string;
+          multiple: boolean;
+          path: string;
+          type: string;
+        }[];
+        description: string;
+        multiple: boolean;
+        simpleType: string;
+      };
       "client-overlay-warnings": {
         configs: {
           type: string;
@@ -417,6 +428,60 @@ declare class Server {
         simpleType: string;
         multiple: boolean;
       };
+      /**
+       * @typedef {Object} WebSocketURL
+       * @property {string} [hostname]
+       * @property {string} [password]
+       * @property {string} [pathname]
+       * @property {number | string} [port]
+       * @property {string} [protocol]
+       * @property {string} [username]
+       */
+      /**
+       * @typedef {Object} ClientConfiguration
+       * @property {"log" | "info" | "warn" | "error" | "none" | "verbose"} [logging]
+       * @property {boolean  | { warnings?: boolean, errors?: boolean }} [overlay]
+       * @property {boolean} [progress]
+       * @property {boolean | number} [reconnect]
+       * @property {"ws" | "sockjs" | string} [webSocketTransport]
+       * @property {string | WebSocketURL} [webSocketURL]
+       */
+      /**
+       * @typedef {Array<{ key: string; value: string }> | Record<string, string | string[]>} Headers
+       */
+      /**
+       * @typedef {{ name?: string, path?: string, middleware: ExpressRequestHandler | ExpressErrorRequestHandler } | ExpressRequestHandler | ExpressErrorRequestHandler} Middleware
+       */
+      /**
+       * @typedef {Object} Configuration
+       * @property {boolean | string} [ipc]
+       * @property {Host} [host]
+       * @property {Port} [port]
+       * @property {boolean | "only"} [hot]
+       * @property {boolean} [liveReload]
+       * @property {DevMiddlewareOptions<Request, Response>} [devMiddleware]
+       * @property {boolean} [compress]
+       * @property {boolean} [magicHtml]
+       * @property {"auto" | "all" | string | string[]} [allowedHosts]
+       * @property {boolean | ConnectHistoryApiFallbackOptions} [historyApiFallback]
+       * @property {boolean} [setupExitSignals]
+       * @property {boolean | Record<string, never> | BonjourOptions} [bonjour]
+       * @property {string | string[] | WatchFiles | Array<string | WatchFiles>} [watchFiles]
+       * @property {boolean | string | Static | Array<string | Static>} [static]
+       * @property {boolean | ServerOptions} [https]
+       * @property {boolean} [http2]
+       * @property {"http" | "https" | "spdy" | string | ServerConfiguration} [server]
+       * @property {boolean | "sockjs" | "ws" | string | WebSocketServerConfiguration} [webSocketServer]
+       * @property {ProxyConfigMap | ProxyConfigArrayItem | ProxyConfigArray} [proxy]
+       * @property {boolean | string | Open | Array<string | Open>} [open]
+       * @property {boolean} [setupExitSignals]
+       * @property {boolean | ClientConfiguration} [client]
+       * @property {Headers | ((req: Request, res: Response, context: DevMiddlewareContext<Request, Response>) => Headers)} [headers]
+       * @property {(devServer: Server) => void} [onAfterSetupMiddleware]
+       * @property {(devServer: Server) => void} [onBeforeSetupMiddleware]
+       * @property {(devServer: Server) => void} [onListening]
+       * @property {(middlewares: Middleware[], devServer: Server) => Middleware[]} [setupMiddlewares]
+       */
       "client-reconnect": {
         configs: (
           | {
@@ -453,36 +518,6 @@ declare class Server {
               path: string;
             }
         )[];
-        /**
-         * @typedef {Object} Configuration
-         * @property {boolean | string} [ipc]
-         * @property {Host} [host]
-         * @property {Port} [port]
-         * @property {boolean | "only"} [hot]
-         * @property {boolean} [liveReload]
-         * @property {DevMiddlewareOptions<Request, Response>} [devMiddleware]
-         * @property {boolean} [compress]
-         * @property {boolean} [magicHtml]
-         * @property {"auto" | "all" | string | string[]} [allowedHosts]
-         * @property {boolean | ConnectHistoryApiFallbackOptions} [historyApiFallback]
-         * @property {boolean} [setupExitSignals]
-         * @property {boolean | Record<string, never> | BonjourOptions} [bonjour]
-         * @property {string | string[] | WatchFiles | Array<string | WatchFiles>} [watchFiles]
-         * @property {boolean | string | Static | Array<string | Static>} [static]
-         * @property {boolean | ServerOptions} [https]
-         * @property {boolean} [http2]
-         * @property {"http" | "https" | "spdy" | string | ServerConfiguration} [server]
-         * @property {boolean | "sockjs" | "ws" | string | WebSocketServerConfiguration} [webSocketServer]
-         * @property {ProxyConfigMap | ProxyConfigArrayItem | ProxyConfigArray} [proxy]
-         * @property {boolean | string | Open | Array<string | Open>} [open]
-         * @property {boolean} [setupExitSignals]
-         * @property {boolean | ClientConfiguration} [client]
-         * @property {Headers | ((req: Request, res: Response, context: DevMiddlewareContext<Request, Response>) => Headers)} [headers]
-         * @property {(devServer: Server) => void} [onAfterSetupMiddleware]
-         * @property {(devServer: Server) => void} [onBeforeSetupMiddleware]
-         * @property {(devServer: Server) => void} [onListening]
-         * @property {(middlewares: Middleware[], devServer: Server) => Middleware[]} [setupMiddlewares]
-         */
         description: string;
         simpleType: string;
         multiple: boolean;
@@ -539,6 +574,9 @@ declare class Server {
           path: string;
         }[];
         description: string;
+        /**
+         * @type {FSWatcher[]}
+         */
         simpleType: string;
         multiple: boolean;
       };
@@ -558,20 +596,12 @@ declare class Server {
               type: string;
             }
         )[];
-        /**
-         * @private
-         * @type {{ name: string | symbol, listener: (...args: any[]) => void}[] }}
-         */
         description: string;
         multiple: boolean;
         simpleType: string;
       };
       "client-web-socket-url-username": {
         configs: {
-          /**
-           * @private
-           * @type {RequestHandler[]}
-           */
           type: string;
           multiple: boolean;
           description: string;
@@ -581,6 +611,10 @@ declare class Server {
         simpleType: string;
         multiple: boolean;
       };
+      /**
+       * @param {string} URL
+       * @returns {boolean}
+       */
       compress: {
         configs: {
           type: string;
@@ -591,6 +625,10 @@ declare class Server {
         }[];
         description: string;
         simpleType: string;
+        /**
+         * @param {string} gateway
+         * @returns {string | undefined}
+         */
         multiple: boolean;
       };
       "history-api-fallback": {
@@ -623,6 +661,10 @@ declare class Server {
         )[];
         description: string;
         simpleType: string;
+        /**
+         * @param {Host} hostname
+         * @returns {Promise<string>}
+         */
         multiple: boolean;
       };
       hot: {
@@ -632,10 +674,6 @@ declare class Server {
               multiple: boolean;
               description: string;
               negatedDescription: string;
-              /**
-               * @param {"v4" | "v6"} family
-               * @returns {string | undefined}
-               */
               path: string;
             }
           | {
@@ -662,11 +700,6 @@ declare class Server {
         simpleType: string;
         multiple: boolean;
       };
-      /**
-       * @param {Port} port
-       * @param {string} host
-       * @returns {Promise<number | string>}
-       */
       https: {
         configs: {
           type: string;
@@ -693,6 +726,9 @@ declare class Server {
       "https-ca-reset": {
         configs: {
           description: string;
+          /**
+           * @type {string[]}
+           */
           multiple: boolean;
           path: string;
           type: string;
@@ -717,7 +753,7 @@ declare class Server {
           description: string;
           multiple: boolean;
           path: string;
-          type: string /** @type {WebSocketURL} */;
+          type: string;
         }[];
         description: string;
         multiple: boolean;
@@ -731,7 +767,7 @@ declare class Server {
           path: string;
         }[];
         description: string;
-        /** @type {ServerConfiguration} */ simpleType: string;
+        simpleType: string;
         multiple: boolean;
       };
       "https-cert-reset": {
@@ -827,7 +863,7 @@ declare class Server {
           type: string;
           multiple: boolean;
           description: string;
-          negatedDescription: string;
+          /** @type {Object<string,string>} */ negatedDescription: string;
           path: string;
         }[];
         description: string;
@@ -839,12 +875,13 @@ declare class Server {
           | {
               type: string;
               multiple: boolean;
+              /** @type {any} */
               description: string;
               path: string;
             }
           | {
               type: string;
-              values: boolean[];
+              /** @type {any} */ values: boolean[];
               multiple: boolean;
               description: string;
               path: string;
@@ -894,7 +931,7 @@ declare class Server {
               path: string;
             }
         )[];
-        description: string;
+        /** @type {Compiler} */ description: string;
         simpleType: string;
         multiple: boolean;
       };
@@ -906,10 +943,6 @@ declare class Server {
           path: string;
         }[];
         description: string;
-        /**
-         * @private
-         * @returns {Promise<void>}
-         */
         simpleType: string;
         multiple: boolean;
       };
@@ -954,13 +987,9 @@ declare class Server {
           path: string;
         }[];
         description: string;
-        simpleType: string;
+        /** @type {NormalizedStatic} */ simpleType: string;
         multiple: boolean;
       };
-      /**
-       * @param {string | Static | undefined} [optionsForStatic]
-       * @returns {NormalizedStatic}
-       */
       "open-target-reset": {
         configs: {
           type: string;
@@ -1127,14 +1156,15 @@ declare class Server {
       "server-options-pfx-reset": {
         configs: {
           description: string;
-          /** @type {ServerConfiguration} */ multiple: boolean;
+          multiple: boolean;
           path: string;
           type: string;
         }[];
         description: string;
         multiple: boolean;
-        simpleType: string;
+        simpleType: string /** @type {ServerOptions} */;
       };
+      /** @type {ServerOptions} */
       "server-options-request-cert": {
         configs: {
           description: string;
@@ -1153,10 +1183,10 @@ declare class Server {
           multiple: boolean;
           path: string;
           type: string;
-          /** @type {ServerOptions} */ values: string[];
+          values: string[];
         }[];
         description: string;
-        /** @type {Array<keyof ServerOptions>} */ multiple: boolean;
+        multiple: boolean;
         simpleType: string;
       };
       static: {
@@ -1170,13 +1200,17 @@ declare class Server {
           | {
               type: string;
               multiple: boolean;
+              /**
+               * @param {string | Buffer | undefined} item
+               * @returns {string | Buffer | undefined}
+               */
               description: string;
               negatedDescription: string;
               path: string;
             }
         )[];
         description: string;
-        /** @type {ServerOptions} */ simpleType: string;
+        simpleType: string;
         multiple: boolean;
       };
       "static-directory": {
@@ -1186,7 +1220,7 @@ declare class Server {
           description: string;
           path: string;
         }[];
-        description: string;
+        /** @type {any} */ description: string;
         simpleType: string;
         multiple: boolean;
       };
@@ -1288,12 +1322,14 @@ declare class Server {
             }
           | {
               description: string;
-              /** @type {ServerOptions & { cacert?: ServerOptions["ca"] }} */ multiple: boolean;
+              multiple: boolean;
               path: string;
               type: string;
             }
         )[];
+        /** @type {ServerOptions & { cacert?: ServerOptions["ca"] }} */
         description: string;
+        /** @type {ServerOptions} */
         simpleType: string;
         multiple: boolean;
       };
@@ -1301,7 +1337,6 @@ declare class Server {
         configs: (
           | {
               description: string;
-              /** @type {ServerOptions & { cacert?: ServerOptions["ca"] }} */
               multiple: boolean;
               path: string;
               type: string;
@@ -1311,12 +1346,12 @@ declare class Server {
               description: string;
               multiple: boolean;
               path: string;
-              /** @type {ServerOptions} */ type: string;
+              type: string;
             }
         )[];
         description: string;
         simpleType: string;
-        /** @type {ServerOptions} */ multiple: boolean;
+        multiple: boolean;
       };
     };
     readonly processArguments: (