diff --git a/README.md b/README.md
index ce466e8c7d..7cadb5cd62 100644
--- a/README.md
+++ b/README.md
@@ -105,11 +105,11 @@ Options:
   --no-client                               Disables client script.
   --client-logging <value>                  Allows to set log level in the browser.
   --client-overlay                          Enables a full-screen overlay in the browser when there are compiler errors or warnings.
-  --no-client-overlay                       Disables a full-screen overlay in the browser when there are compiler errors or warnings.
+  --no-client-overlay                       Disables the full-screen overlay in the browser when there are compiler errors or warnings.
   --client-overlay-errors                   Enables a full-screen overlay in the browser when there are compiler errors.
-  --no-client-overlay-errors                Negative 'client-overlay-errors' option.
+  --no-client-overlay-errors                Disables the full-screen overlay in the browser when there are compiler errors.
   --client-overlay-warnings                 Enables a full-screen overlay in the browser when there are compiler warnings.
-  --no-client-overlay-warnings              Negative 'client-overlay-warnings' option.
+  --no-client-overlay-warnings              Disables the full-screen overlay in the browser when there are compiler warnings.
   --client-progress                         Prints compilation progress in percentage in the browser.
   --no-client-progress                      Does not print compilation progress in percentage in the browser.
   --client-reconnect [value]                Tells dev-server the number of times it should try to reconnect the client.
diff --git a/bin/cli-flags.js b/bin/cli-flags.js
index 7dabe089bf..1f1376ef75 100644
--- a/bin/cli-flags.js
+++ b/bin/cli-flags.js
@@ -95,7 +95,7 @@ module.exports = {
         description:
           "Enables a full-screen overlay in the browser when there are compiler errors or warnings.",
         negatedDescription:
-          "Disables a full-screen overlay in the browser when there are compiler errors or warnings.",
+          "Disables the full-screen overlay in the browser when there are compiler errors or warnings.",
         path: "client.overlay",
       },
     ],
@@ -111,6 +111,8 @@ module.exports = {
         multiple: false,
         description:
           "Enables a full-screen overlay in the browser when there are compiler errors.",
+        negatedDescription:
+          "Disables the full-screen overlay in the browser when there are compiler errors.",
         path: "client.overlay.errors",
       },
     ],
@@ -126,6 +128,8 @@ module.exports = {
         multiple: false,
         description:
           "Enables a full-screen overlay in the browser when there are compiler warnings.",
+        negatedDescription:
+          "Disables the full-screen overlay in the browser when there are compiler warnings.",
         path: "client.overlay.warnings",
       },
     ],
@@ -1026,6 +1030,7 @@ module.exports = {
     configs: [
       {
         description: "Request for an SSL certificate.",
+        negatedDescription: "Does not request for an SSL certificate.",
         multiple: false,
         path: "server.options.requestCert",
         type: "boolean",
@@ -1063,6 +1068,8 @@ module.exports = {
         multiple: false,
         description:
           "Allows to configure options for serving static files from directory (by default 'public' directory).",
+        negatedDescription:
+          "Disallows to configure options for serving static files from directory.",
         path: "static",
       },
     ],
@@ -1202,6 +1209,7 @@ module.exports = {
       {
         description:
           "Deprecated: please use '--web-socket-server-type' option.",
+        negatedDescription: "Disallows to set web socket server and options.",
         multiple: false,
         path: "webSocketServer",
         type: "enum",
diff --git a/lib/options.json b/lib/options.json
index af3ce99c66..32b1c84ca1 100644
--- a/lib/options.json
+++ b/lib/options.json
@@ -90,7 +90,7 @@
           "link": "https://webpack.js.org/configuration/dev-server/#overlay",
           "type": "boolean",
           "cli": {
-            "negatedDescription": "Disables a full-screen overlay in the browser when there are compiler errors or warnings."
+            "negatedDescription": "Disables the full-screen overlay in the browser when there are compiler errors or warnings."
           }
         },
         {
@@ -99,11 +99,17 @@
           "properties": {
             "errors": {
               "description": "Enables a full-screen overlay in the browser when there are compiler errors.",
-              "type": "boolean"
+              "type": "boolean",
+              "cli": {
+                "negatedDescription": "Disables the full-screen overlay in the browser when there are compiler errors."
+              }
             },
             "warnings": {
               "description": "Enables a full-screen overlay in the browser when there are compiler warnings.",
-              "type": "boolean"
+              "type": "boolean",
+              "cli": {
+                "negatedDescription": "Disables the full-screen overlay in the browser when there are compiler warnings."
+              }
             }
           }
         }
@@ -737,7 +743,10 @@
         },
         "requestCert": {
           "type": "boolean",
-          "description": "Request for an SSL certificate."
+          "description": "Request for an SSL certificate.",
+          "cli": {
+            "negatedDescription": "Does not request for an SSL certificate."
+          }
         },
         "ca": {
           "anyOf": [
@@ -922,7 +931,10 @@
           }
         },
         {
-          "type": "boolean"
+          "type": "boolean",
+          "cli": {
+            "negatedDescription": "Disallows to configure options for serving static files from directory."
+          }
         },
         {
           "$ref": "#/definitions/StaticString"
@@ -1088,7 +1100,10 @@
     "WebSocketServerEnum": {
       "anyOf": [
         {
-          "enum": [false]
+          "enum": [false],
+          "cli": {
+            "negatedDescription": "Disallows to set web socket server and options."
+          }
         },
         {
           "$ref": "#/definitions/WebSocketServerType"
diff --git a/test/cli/__snapshots__/basic.test.js.snap.webpack4 b/test/cli/__snapshots__/basic.test.js.snap.webpack4
index be4df73a65..6b2237bbd7 100644
--- a/test/cli/__snapshots__/basic.test.js.snap.webpack4
+++ b/test/cli/__snapshots__/basic.test.js.snap.webpack4
@@ -61,11 +61,11 @@ Options:
   --no-client                               Disables client script.
   --client-logging <value>                  Allows to set log level in the browser.
   --client-overlay                          Enables a full-screen overlay in the browser when there are compiler errors or warnings.
-  --no-client-overlay                       Disables a full-screen overlay in the browser when there are compiler errors or warnings.
+  --no-client-overlay                       Disables the full-screen overlay in the browser when there are compiler errors or warnings.
   --client-overlay-errors                   Enables a full-screen overlay in the browser when there are compiler errors.
-  --no-client-overlay-errors                Negative 'client-overlay-errors' option.
+  --no-client-overlay-errors                Disables the full-screen overlay in the browser when there are compiler errors.
   --client-overlay-warnings                 Enables a full-screen overlay in the browser when there are compiler warnings.
-  --no-client-overlay-warnings              Negative 'client-overlay-warnings' option.
+  --no-client-overlay-warnings              Disables the full-screen overlay in the browser when there are compiler warnings.
   --client-progress                         Prints compilation progress in percentage in the browser.
   --no-client-progress                      Does not print compilation progress in percentage in the browser.
   --client-reconnect [value]                Tells dev-server the number of times it should try to reconnect the client.
@@ -132,10 +132,10 @@ Options:
   --server-options-pfx <value...>           Path to an SSL pfx file or content of an SSL pfx file.
   --server-options-pfx-reset                Clear all items provided in 'server.options.pfx' configuration. Path to an SSL pfx file or content of an SSL pfx file.
   --server-options-request-cert             Request for an SSL certificate.
-  --no-server-options-request-cert          Negative 'server-options-request-cert' option.
+  --no-server-options-request-cert          Does not request for an SSL certificate.
   --server-type <value>                     Allows to set server and options (by default 'http').
   --static [value...]                       Allows to configure options for serving static files from directory (by default 'public' directory).
-  --no-static                               Negative 'static' option.
+  --no-static                               Disallows to configure options for serving static files from directory.
   --static-directory <value...>             Directory for static contents.
   --static-public-path <value...>           The static files will be available in the browser under this public path.
   --static-public-path-reset                Clear all items provided in 'static.publicPath' configuration. The static files will be available in the browser under this public path.
@@ -147,7 +147,7 @@ Options:
   --watch-files <value...>                  Allows to configure list of globs/directories/files to watch for file changes.
   --watch-files-reset                       Clear all items provided in 'watchFiles' configuration. Allows to configure list of globs/directories/files to watch for file changes.
   --web-socket-server <value>               Deprecated: please use '--web-socket-server-type' option. Allows to set web socket server and options (by default 'ws').
-  --no-web-socket-server                    Negative 'web-socket-server' option.
+  --no-web-socket-server                    Disallows to set web socket server and options.
   --web-socket-server-type <value>          Allows to set web socket server and options (by default 'ws').
 
 Global options:
diff --git a/test/cli/__snapshots__/basic.test.js.snap.webpack5 b/test/cli/__snapshots__/basic.test.js.snap.webpack5
index 5960150dd8..3649bb9ee5 100644
--- a/test/cli/__snapshots__/basic.test.js.snap.webpack5
+++ b/test/cli/__snapshots__/basic.test.js.snap.webpack5
@@ -62,11 +62,11 @@ Options:
   --no-client                               Disables client script.
   --client-logging <value>                  Allows to set log level in the browser.
   --client-overlay                          Enables a full-screen overlay in the browser when there are compiler errors or warnings.
-  --no-client-overlay                       Disables a full-screen overlay in the browser when there are compiler errors or warnings.
+  --no-client-overlay                       Disables the full-screen overlay in the browser when there are compiler errors or warnings.
   --client-overlay-errors                   Enables a full-screen overlay in the browser when there are compiler errors.
-  --no-client-overlay-errors                Negative 'client-overlay-errors' option.
+  --no-client-overlay-errors                Disables the full-screen overlay in the browser when there are compiler errors.
   --client-overlay-warnings                 Enables a full-screen overlay in the browser when there are compiler warnings.
-  --no-client-overlay-warnings              Negative 'client-overlay-warnings' option.
+  --no-client-overlay-warnings              Disables the full-screen overlay in the browser when there are compiler warnings.
   --client-progress                         Prints compilation progress in percentage in the browser.
   --no-client-progress                      Does not print compilation progress in percentage in the browser.
   --client-reconnect [value]                Tells dev-server the number of times it should try to reconnect the client.
@@ -122,7 +122,7 @@ Options:
   --server-type <value>                     Allows to set server and options (by default 'http').
   --server-options-passphrase <value>       Passphrase for a pfx file.
   --server-options-request-cert             Request for an SSL certificate.
-  --no-server-options-request-cert          Negative 'server-options-request-cert' option.
+  --no-server-options-request-cert          Does not request for an SSL certificate.
   --server-options-ca <value...>            Path to an SSL CA certificate or content of an SSL CA certificate.
   --server-options-ca-reset                 Clear all items provided in 'server.options.ca' configuration. Path to an SSL CA certificate or content of an SSL CA certificate.
   --server-options-cacert <value...>        Path to an SSL CA certificate or content of an SSL CA certificate. Deprecated, use the \`server.options.ca\` option.
@@ -136,7 +136,7 @@ Options:
   --server-options-pfx <value...>           Path to an SSL pfx file or content of an SSL pfx file.
   --server-options-pfx-reset                Clear all items provided in 'server.options.pfx' configuration. Path to an SSL pfx file or content of an SSL pfx file.
   --static [value...]                       Allows to configure options for serving static files from directory (by default 'public' directory).
-  --no-static                               Negative 'static' option.
+  --no-static                               Disallows to configure options for serving static files from directory.
   --static-directory <value...>             Directory for static contents.
   --static-public-path <value...>           The static files will be available in the browser under this public path.
   --static-serve-index                      Tells dev server to use serveIndex middleware when enabled.
@@ -148,7 +148,7 @@ Options:
   --watch-files <value...>                  Allows to configure list of globs/directories/files to watch for file changes.
   --watch-files-reset                       Clear all items provided in 'watchFiles' configuration. Allows to configure list of globs/directories/files to watch for file changes.
   --web-socket-server <value>               Deprecated: please use '--web-socket-server-type' option. Allows to set web socket server and options (by default 'ws').
-  --no-web-socket-server                    Negative 'web-socket-server' option.
+  --no-web-socket-server                    Disallows to set web socket server and options.
   --web-socket-server-type <value>          Allows to set web socket server and options (by default 'ws').
 
 Global options:
diff --git a/types/bin/cli-flags.d.ts b/types/bin/cli-flags.d.ts
index 876cd64b2b..fa98132496 100644
--- a/types/bin/cli-flags.d.ts
+++ b/types/bin/cli-flags.d.ts
@@ -84,6 +84,7 @@ declare const _exports: {
       type: string;
       multiple: boolean;
       description: string;
+      negatedDescription: string;
       path: string;
     }[];
     description: string;
@@ -95,6 +96,7 @@ declare const _exports: {
       type: string;
       multiple: boolean;
       description: string;
+      negatedDescription: string;
       path: string;
     }[];
     description: string;
@@ -779,6 +781,7 @@ declare const _exports: {
   "server-options-request-cert": {
     configs: {
       description: string;
+      negatedDescription: string;
       multiple: boolean;
       path: string;
       type: string;
@@ -800,12 +803,21 @@ declare const _exports: {
     simpleType: string;
   };
   static: {
-    configs: {
-      type: string;
-      multiple: boolean;
-      description: string;
-      path: string;
-    }[];
+    configs: (
+      | {
+          type: string;
+          multiple: boolean;
+          description: string;
+          path: string;
+        }
+      | {
+          type: string;
+          multiple: boolean;
+          description: string;
+          negatedDescription: string;
+          path: string;
+        }
+    )[];
     description: string;
     simpleType: string;
     multiple: boolean;
@@ -904,6 +916,7 @@ declare const _exports: {
     configs: (
       | {
           description: string;
+          negatedDescription: string;
           multiple: boolean;
           path: string;
           type: string;
diff --git a/types/lib/Server.d.ts b/types/lib/Server.d.ts
index 29e3f65302..50294755aa 100644
--- a/types/lib/Server.d.ts
+++ b/types/lib/Server.d.ts
@@ -394,110 +394,8 @@ declare class Server {
            * @property {ServeStaticOptions} staticOptions
            * @property {false | WatchOptions} watch
            */
-          /**
-           * @typedef {Object} ServerConfiguration
-           * @property {"http" | "https" | "spdy" | string} [type]
-           * @property {ServerOptions} [options]
-           */
-          /**
-           * @typedef {Object} WebSocketServerConfiguration
-           * @property {"sockjs" | "ws" | string | Function} [type]
-           * @property {Record<string, any>} [options]
-           */
-          /**
-           * @typedef {(import("ws").WebSocket | import("sockjs").Connection & { send: import("ws").WebSocket["send"], terminate: import("ws").WebSocket["terminate"], ping: import("ws").WebSocket["ping"] }) & { isAlive?: boolean }} ClientConnection
-           */
-          /**
-           * @typedef {import("ws").WebSocketServer | import("sockjs").Server & { close: import("ws").WebSocketServer["close"] }} WebSocketServer
-           */
-          /**
-           * @typedef {{ implementation: WebSocketServer, clients: ClientConnection[] }} WebSocketServerImplementation
-           */
-          /**
-           * @callback ByPass
-           * @param {Request} req
-           * @param {Response} res
-           * @param {ProxyConfigArrayItem} proxyConfig
-           */
-          /**
-           * @typedef {{ path?: HttpProxyMiddlewareOptionsFilter | undefined, context?: HttpProxyMiddlewareOptionsFilter | undefined } & { bypass?: ByPass } & HttpProxyMiddlewareOptions } ProxyConfigArrayItem
-           */
-          /**
-           * @typedef {(ProxyConfigArrayItem | ((req?: Request | undefined, res?: Response | undefined, next?: NextFunction | undefined) => ProxyConfigArrayItem))[]} ProxyConfigArray
-           */
-          /**
-           * @typedef {{ [url: string]: string | ProxyConfigArrayItem }} ProxyConfigMap
-           */
-          /**
-           * @typedef {Object} OpenApp
-           * @property {string} [name]
-           * @property {string[]} [arguments]
-           */
-          /**
-           * @typedef {Object} Open
-           * @property {string | string[] | OpenApp} [app]
-           * @property {string | string[]} [target]
-           */
-          /**
-           * @typedef {Object} NormalizedOpen
-           * @property {string} target
-           * @property {import("open").Options} options
-           */
-          /**
-           * @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 | 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;
+          negatedDescription: string;
           path: string;
         }[];
         description: string;
@@ -507,106 +405,9 @@ declare class Server {
       "client-overlay-warnings": {
         configs: {
           type: string;
-          /**
-           * @typedef {Object} WebSocketServerConfiguration
-           * @property {"sockjs" | "ws" | string | Function} [type]
-           * @property {Record<string, any>} [options]
-           */
-          /**
-           * @typedef {(import("ws").WebSocket | import("sockjs").Connection & { send: import("ws").WebSocket["send"], terminate: import("ws").WebSocket["terminate"], ping: import("ws").WebSocket["ping"] }) & { isAlive?: boolean }} ClientConnection
-           */
-          /**
-           * @typedef {import("ws").WebSocketServer | import("sockjs").Server & { close: import("ws").WebSocketServer["close"] }} WebSocketServer
-           */
-          /**
-           * @typedef {{ implementation: WebSocketServer, clients: ClientConnection[] }} WebSocketServerImplementation
-           */
-          /**
-           * @callback ByPass
-           * @param {Request} req
-           * @param {Response} res
-           * @param {ProxyConfigArrayItem} proxyConfig
-           */
-          /**
-           * @typedef {{ path?: HttpProxyMiddlewareOptionsFilter | undefined, context?: HttpProxyMiddlewareOptionsFilter | undefined } & { bypass?: ByPass } & HttpProxyMiddlewareOptions } ProxyConfigArrayItem
-           */
-          /**
-           * @typedef {(ProxyConfigArrayItem | ((req?: Request | undefined, res?: Response | undefined, next?: NextFunction | undefined) => ProxyConfigArrayItem))[]} ProxyConfigArray
-           */
-          /**
-           * @typedef {{ [url: string]: string | ProxyConfigArrayItem }} ProxyConfigMap
-           */
-          /**
-           * @typedef {Object} OpenApp
-           * @property {string} [name]
-           * @property {string[]} [arguments]
-           */
-          /**
-           * @typedef {Object} Open
-           * @property {string | string[] | OpenApp} [app]
-           * @property {string | string[]} [target]
-           */
-          /**
-           * @typedef {Object} NormalizedOpen
-           * @property {string} target
-           * @property {import("open").Options} options
-           */
-          /**
-           * @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 | 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]
-           */
           multiple: boolean;
           description: string;
+          negatedDescription: string;
           path: string;
         }[];
         description: string;
@@ -632,6 +433,65 @@ declare class Server {
               multiple: boolean;
               description: string;
               negatedDescription: string;
+              /**
+               * @typedef {Object} NormalizedOpen
+               * @property {string} target
+               * @property {import("open").Options} options
+               */
+              /**
+               * @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 | 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]
+               */
               path: string;
             }
           | {
@@ -727,6 +587,9 @@ declare class Server {
               multiple: boolean;
               path: string;
               type: string;
+              /**
+               * @type {ReturnType<Compiler["getInfrastructureLogger"]>}
+               * */
               values: string[];
             }
           | {
@@ -830,6 +693,10 @@ declare class Server {
       };
       https: {
         configs: {
+          /**
+           * @param {Port} port
+           * @returns {Promise<number | string>}
+           */
           type: string;
           multiple: boolean;
           description: string;
@@ -880,9 +747,9 @@ declare class Server {
           path: string;
           type: string;
         }[];
-        description: string;
+        /** @type {WebSocketURL} */ description: string;
         multiple: boolean;
-        simpleType: string /** @type {WebSocketURL} */;
+        simpleType: string;
       };
       "https-cert": {
         configs: {
@@ -893,7 +760,7 @@ declare class Server {
         }[];
         description: string;
         simpleType: string;
-        multiple: boolean;
+        /** @type {ServerConfiguration} */ multiple: boolean;
       };
       "https-cert-reset": {
         configs: {
@@ -942,7 +809,7 @@ declare class Server {
       "https-key-reset": {
         configs: {
           description: string;
-          multiple: boolean;
+          /** @type {string} */ multiple: boolean;
           path: string;
           type: string;
         }[];
@@ -1006,6 +873,7 @@ declare class Server {
           | {
               type: string;
               values: boolean[];
+              /** @type {Object<string,string>} */
               multiple: boolean;
               description: string;
               path: string;
@@ -1050,7 +918,6 @@ declare class Server {
           | {
               type: string;
               multiple: boolean;
-              /** @type {MultiCompiler} */
               description: string;
               negatedDescription: string;
               path: string;
@@ -1122,10 +989,6 @@ declare class Server {
           description: string;
           path: string;
         }[];
-        /**
-         * @param {string | Static | undefined} [optionsForStatic]
-         * @returns {NormalizedStatic}
-         */
         description: string;
         simpleType: string;
         multiple: boolean;
@@ -1296,6 +1159,7 @@ declare class Server {
       "server-options-request-cert": {
         configs: {
           description: string;
+          negatedDescription: string;
           multiple: boolean;
           path: string;
           type: string;
@@ -1314,18 +1178,27 @@ declare class Server {
         }[];
         description: string;
         multiple: boolean;
-        simpleType: string;
+        /** @type {Array<keyof ServerOptions>} */ simpleType: string;
       };
       static: {
-        configs: {
-          /** @type {ServerOptions} */ type: string;
-          multiple: boolean;
-          description: string;
-          path: string;
-        }[];
+        configs: (
+          | {
+              type: string;
+              multiple: boolean;
+              description: string;
+              path: string;
+            }
+          | {
+              type: string;
+              multiple: boolean;
+              description: string;
+              negatedDescription: string;
+              path: string;
+            }
+        )[];
         description: string;
         simpleType: string;
-        multiple: boolean;
+        /** @type {ServerOptions} */ multiple: boolean;
       };
       "static-directory": {
         configs: {
@@ -1421,6 +1294,7 @@ declare class Server {
         configs: (
           | {
               description: string;
+              negatedDescription: string;
               multiple: boolean;
               path: string;
               type: string;
@@ -1457,14 +1331,13 @@ declare class Server {
               description: string;
               multiple: boolean;
               path: string;
-              type: string;
+              type: string /** @type {ServerOptions} */;
             }
         )[];
         description: string;
         simpleType: string;
-        /** @type {ServerOptions & { cacert?: ServerOptions["ca"] }} */
-        multiple: boolean;
-      };
+        multiple: boolean /** @type {ServerOptions} */;
+      } /** @type {ServerOptions} */;
     };
     readonly processArguments: (
       args: Record<string, import("../bin/process-arguments").Argument>,
@@ -1745,10 +1618,16 @@ declare class Server {
                 errors: {
                   description: string;
                   type: string;
+                  cli: {
+                    negatedDescription: string;
+                  };
                 };
                 warnings: {
                   description: string;
                   type: string;
+                  cli: {
+                    negatedDescription: string;
+                  };
                 };
               };
               description?: undefined;
@@ -1771,6 +1650,93 @@ declare class Server {
         anyOf: (
           | {
               type: string;
+              /**
+               * @typedef {{ implementation: WebSocketServer, clients: ClientConnection[] }} WebSocketServerImplementation
+               */
+              /**
+               * @callback ByPass
+               * @param {Request} req
+               * @param {Response} res
+               * @param {ProxyConfigArrayItem} proxyConfig
+               */
+              /**
+               * @typedef {{ path?: HttpProxyMiddlewareOptionsFilter | undefined, context?: HttpProxyMiddlewareOptionsFilter | undefined } & { bypass?: ByPass } & HttpProxyMiddlewareOptions } ProxyConfigArrayItem
+               */
+              /**
+               * @typedef {(ProxyConfigArrayItem | ((req?: Request | undefined, res?: Response | undefined, next?: NextFunction | undefined) => ProxyConfigArrayItem))[]} ProxyConfigArray
+               */
+              /**
+               * @typedef {{ [url: string]: string | ProxyConfigArrayItem }} ProxyConfigMap
+               */
+              /**
+               * @typedef {Object} OpenApp
+               * @property {string} [name]
+               * @property {string[]} [arguments]
+               */
+              /**
+               * @typedef {Object} Open
+               * @property {string | string[] | OpenApp} [app]
+               * @property {string | string[]} [target]
+               */
+              /**
+               * @typedef {Object} NormalizedOpen
+               * @property {string} target
+               * @property {import("open").Options} options
+               */
+              /**
+               * @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 | 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]
+               */
               cli: {
                 negatedDescription: string;
               };
@@ -1787,6 +1753,81 @@ declare class Server {
         anyOf: {
           $ref: string;
         }[];
+        /**
+         * @typedef {(ProxyConfigArrayItem | ((req?: Request | undefined, res?: Response | undefined, next?: NextFunction | undefined) => ProxyConfigArrayItem))[]} ProxyConfigArray
+         */
+        /**
+         * @typedef {{ [url: string]: string | ProxyConfigArrayItem }} ProxyConfigMap
+         */
+        /**
+         * @typedef {Object} OpenApp
+         * @property {string} [name]
+         * @property {string[]} [arguments]
+         */
+        /**
+         * @typedef {Object} Open
+         * @property {string | string[] | OpenApp} [app]
+         * @property {string | string[]} [target]
+         */
+        /**
+         * @typedef {Object} NormalizedOpen
+         * @property {string} target
+         * @property {import("open").Options} options
+         */
+        /**
+         * @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 | 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;
         link: string;
       };
@@ -1923,6 +1964,10 @@ declare class Server {
                                 type?: undefined;
                               }
                           )[];
+                          /**
+                           * @private
+                           * @type {{ name: string | symbol, listener: (...args: any[]) => void}[] }}
+                           */
                         };
                         instanceof?: undefined;
                       }
@@ -1937,8 +1982,16 @@ declare class Server {
                         items?: undefined;
                       }
                   )[];
+                  /**
+                   * @private
+                   * @type {RequestHandler[]}
+                   */
                   description: string;
                 };
+                /**
+                 * @private
+                 * @type {string | undefined}
+                 */
                 cacert: {
                   anyOf: (
                     | {
@@ -1951,10 +2004,6 @@ declare class Server {
                               }
                             | {
                                 instanceof: string;
-                                /**
-                                 * @private
-                                 * @type {string | undefined}
-                                 */
                                 type?: undefined;
                               }
                           )[];
@@ -2111,9 +2160,6 @@ declare class Server {
                       }
                   )[];
                   description: string;
-                  /**
-                   * @returns {string}
-                   */
                 };
               };
               cli?: undefined /** @typedef {import("express").Request} Request */;
@@ -2179,6 +2225,7 @@ declare class Server {
               type: string;
               description: string;
               link: string;
+              /** @type {{ type: WebSocketServerConfiguration["type"], options: NonNullable<WebSocketServerConfiguration["options"]> }} */
               cli?: undefined /** @typedef {import("express").Request} Request */;
             }
         )[];
@@ -2264,7 +2311,7 @@ declare class Server {
       OnListening: {
         instanceof: string;
         description: string;
-        link: string;
+        /** @type {string} */ link: string;
       };
       Open: {
         anyOf: (
@@ -2383,6 +2430,7 @@ declare class Server {
               enum?: undefined;
             }
           | {
+              /** @type {any} */
               enum: string[];
               type?: undefined;
               minimum?: undefined;
@@ -2390,6 +2438,7 @@ declare class Server {
               minLength?: undefined;
             }
         )[];
+        /** @type {any} */
         description: string;
         link: string;
       };
@@ -2402,7 +2451,6 @@ declare class Server {
           | {
               type: string;
               items: {
-                /** @type {any} */
                 anyOf: (
                   | {
                       type: string;
@@ -2437,7 +2485,7 @@ declare class Server {
       };
       ServerString: {
         type: string;
-        /** @type {MultiCompiler} */ minLength: number;
+        minLength: number;
         cli: {
           exclude: boolean;
         };
@@ -2467,6 +2515,9 @@ declare class Server {
           requestCert: {
             type: string;
             description: string;
+            cli: {
+              negatedDescription: string;
+            };
           };
           ca: {
             anyOf: (
@@ -2585,6 +2636,7 @@ declare class Server {
                   instanceof?: undefined;
                 }
               | {
+                  /** @type {NormalizedStatic} */
                   instanceof: string;
                   type?: undefined;
                   items?: undefined;
@@ -2692,10 +2744,14 @@ declare class Server {
                   $ref: string;
                 }[];
               };
+              cli?: undefined /** @typedef {import("express").Request} Request */;
               $ref?: undefined;
             }
           | {
               type: string;
+              cli: {
+                negatedDescription: string;
+              };
               items?: undefined;
               $ref?: undefined;
             }
@@ -2703,6 +2759,7 @@ declare class Server {
               $ref: string;
               type?: undefined;
               items?: undefined;
+              cli?: undefined /** @typedef {import("express").Request} Request */;
             }
         )[];
         description: string;
@@ -2856,11 +2913,16 @@ declare class Server {
         anyOf: (
           | {
               enum: boolean[];
+              /** @type {ServerOptions} */
+              cli: {
+                negatedDescription: string;
+              };
               $ref?: undefined;
             }
           | {
               $ref: string;
               enum?: undefined;
+              cli?: undefined /** @typedef {import("express").Request} Request */;
             }
         )[];
         cli: {
@@ -2875,7 +2937,7 @@ declare class Server {
         properties: {
           type: {
             anyOf: {
-              $ref: string;
+              $ref: string /** @type {ServerOptions} */;
             }[];
           };
           options: {
@@ -2898,14 +2960,13 @@ declare class Server {
       allowedHosts: {
         $ref: string;
       };
-      /** @type {any} */
       bonjour: {
-        $ref: string /** @type {ServerOptions} */;
+        $ref: string;
       };
-      /** @type {ServerOptions} */
       client: {
         $ref: string;
       };
+      /** @type {any} */
       compress: {
         $ref: string;
       };
@@ -2916,8 +2977,9 @@ declare class Server {
         $ref: string;
       };
       historyApiFallback: {
-        $ref: string;
+        $ref: string /** @type {ServerOptions} */;
       };
+      /** @type {ServerOptions} */
       host: {
         $ref: string;
       };
@@ -2937,7 +2999,7 @@ declare class Server {
         $ref: string;
       };
       magicHtml: {
-        $ref: string /** @type {any} */;
+        $ref: string;
       };
       onAfterSetupMiddleware: {
         $ref: string;