diff --git a/lib/Server.js b/lib/Server.js
index a168fb1c4e..8c6451b43b 100644
--- a/lib/Server.js
+++ b/lib/Server.js
@@ -1272,53 +1272,6 @@ class Server {
      * }
      */
     if (typeof options.proxy !== "undefined") {
-      // TODO remove in the next major release, only accept `Array`
-      if (!Array.isArray(options.proxy)) {
-        if (
-          Object.prototype.hasOwnProperty.call(options.proxy, "target") ||
-          Object.prototype.hasOwnProperty.call(options.proxy, "router")
-        ) {
-          /** @type {ProxyConfigArray} */
-          (options.proxy) = [/** @type {ProxyConfigMap} */ (options.proxy)];
-        } else {
-          /** @type {ProxyConfigArray} */
-          (options.proxy) = Object.keys(options.proxy).map(
-            /**
-             * @param {string} context
-             * @returns {HttpProxyMiddlewareOptions}
-             */
-            (context) => {
-              let proxyOptions;
-              // For backwards compatibility reasons.
-              const correctedContext = context
-                .replace(/^\*$/, "**")
-                .replace(/\/\*$/, "");
-
-              if (
-                typeof (
-                  /** @type {ProxyConfigMap} */ (options.proxy)[context]
-                ) === "string"
-              ) {
-                proxyOptions = {
-                  context: correctedContext,
-                  target:
-                    /** @type {ProxyConfigMap} */
-                    (options.proxy)[context],
-                };
-              } else {
-                proxyOptions = {
-                  // @ts-ignore
-                  .../** @type {ProxyConfigMap} */ (options.proxy)[context],
-                };
-                proxyOptions.context = correctedContext;
-              }
-
-              return proxyOptions;
-            }
-          );
-        }
-      }
-
       /** @type {ProxyConfigArray} */
       (options.proxy) =
         /** @type {ProxyConfigArray} */
diff --git a/lib/options.json b/lib/options.json
index f463557476..400783783f 100644
--- a/lib/options.json
+++ b/lib/options.json
@@ -467,24 +467,17 @@
       "link": "https://webpack.js.org/configuration/dev-server/#devserverport"
     },
     "Proxy": {
-      "anyOf": [
-        {
-          "type": "object"
-        },
-        {
-          "type": "array",
-          "items": {
-            "anyOf": [
-              {
-                "type": "object"
-              },
-              {
-                "instanceof": "Function"
-              }
-            ]
+      "type": "array",
+      "items": {
+        "anyOf": [
+          {
+            "type": "object"
+          },
+          {
+            "instanceof": "Function"
           }
-        }
-      ],
+        ]
+      },
       "description": "Allows to proxy requests, can be useful when you have a separate API backend development server and you want to send API requests on the same domain.",
       "link": "https://webpack.js.org/configuration/dev-server/#devserverproxy"
     },
diff --git a/test/__snapshots__/validate-options.test.js.snap.webpack5 b/test/__snapshots__/validate-options.test.js.snap.webpack5
index d0359d6adb..dde6c25cb9 100644
--- a/test/__snapshots__/validate-options.test.js.snap.webpack5
+++ b/test/__snapshots__/validate-options.test.js.snap.webpack5
@@ -474,28 +474,26 @@ exports[`options validate should throw an error on the "port" option with 'null'
 
 exports[`options validate should throw an error on the "proxy" option with '() => {}' value 1`] = `
 "ValidationError: Invalid options object. Dev Server has been initialized using an options object that does not match the API schema.
- - options.proxy should be one of these:
-   object { … } | [object { … } | function, ...]
+ - options.proxy should be an array:
+   [object { … } | function, ...]
    -> Allows to proxy requests, can be useful when you have a separate API backend development server and you want to send API requests on the same domain.
-   -> Read more at https://webpack.js.org/configuration/dev-server/#devserverproxy
-   Details:
-    * options.proxy should be an object:
-      object { … }
-    * options.proxy should be an array:
-      [object { … } | function, ...]"
+   -> Read more at https://webpack.js.org/configuration/dev-server/#devserverproxy"
+`;
+
+exports[`options validate should throw an error on the "proxy" option with '{"/api":"http://localhost:3000"}' value 1`] = `
+"ValidationError: Invalid options object. Dev Server has been initialized using an options object that does not match the API schema.
+ - options.proxy should be an array:
+   [object { … } | function, ...]
+   -> Allows to proxy requests, can be useful when you have a separate API backend development server and you want to send API requests on the same domain.
+   -> Read more at https://webpack.js.org/configuration/dev-server/#devserverproxy"
 `;
 
 exports[`options validate should throw an error on the "proxy" option with 'false' value 1`] = `
 "ValidationError: Invalid options object. Dev Server has been initialized using an options object that does not match the API schema.
- - options.proxy should be one of these:
-   object { … } | [object { … } | function, ...]
+ - options.proxy should be an array:
+   [object { … } | function, ...]
    -> Allows to proxy requests, can be useful when you have a separate API backend development server and you want to send API requests on the same domain.
-   -> Read more at https://webpack.js.org/configuration/dev-server/#devserverproxy
-   Details:
-    * options.proxy should be an object:
-      object { … }
-    * options.proxy should be an array:
-      [object { … } | function, ...]"
+   -> Read more at https://webpack.js.org/configuration/dev-server/#devserverproxy"
 `;
 
 exports[`options validate should throw an error on the "server" option with '{"type":"https","additional":"test"}' value 1`] = `
diff --git a/test/server/proxy-option.test.js b/test/server/proxy-option.test.js
index f5ffcf2857..947f2a3864 100644
--- a/test/server/proxy-option.test.js
+++ b/test/server/proxy-option.test.js
@@ -13,15 +13,18 @@ const [port1, port2, port3, port4] = require("../ports-map")["proxy-option"];
 const WebSocketServer = WebSocket.Server;
 const staticDirectory = path.resolve(__dirname, "../fixtures/proxy-config");
 
-const proxyOptionPathsAsProperties = {
-  "/proxy1": {
+const proxyOptionPathsAsProperties = [
+  {
+    context: "/proxy1",
     target: `http://localhost:${port1}`,
   },
-  "/api/proxy2": {
+  {
+    context: "/api/proxy2",
     target: `http://localhost:${port2}`,
     pathRewrite: { "^/api": "" },
   },
-  "/foo": {
+  {
+    context: "/foo",
     bypass(req) {
       if (/\.html$/.test(req.path)) {
         return "/index.html";
@@ -30,14 +33,16 @@ const proxyOptionPathsAsProperties = {
       return null;
     },
   },
-  "/proxyfalse": {
+  {
+    context: "proxyfalse",
     bypass(req) {
       if (/\/proxyfalse$/.test(req.path)) {
         return false;
       }
     },
   },
-  "/proxy/async": {
+  {
+    context: "/proxy/async",
     bypass(req, res) {
       if (/\/proxy\/async$/.test(req.path)) {
         return new Promise((resolve) => {
@@ -49,7 +54,8 @@ const proxyOptionPathsAsProperties = {
       }
     },
   },
-  "/bypass-with-target": {
+  {
+    context: "/bypass-with-target",
     target: `http://localhost:${port1}`,
     changeOrigin: true,
     secure: false,
@@ -59,15 +65,17 @@ const proxyOptionPathsAsProperties = {
       }
     },
   },
-};
+];
 
-const proxyOption = {
-  context: () => true,
-  target: `http://localhost:${port1}`,
-};
+const proxyOption = [
+  {
+    context: () => true,
+    target: `http://localhost:${port1}`,
+  },
+];
 
 const proxyOptionOfArray = [
-  { context: "/proxy1", target: proxyOption.target },
+  { context: "/proxy1", target: `http://localhost:${port1}` },
   function proxy(req, res, next) {
     return {
       context: "/api/proxy2",
@@ -90,20 +98,26 @@ const proxyOptionOfArrayWithoutTarget = [
   },
 ];
 
-const proxyWithPath = {
-  "/proxy1": {
+const proxyWithPath = [
+  {
+    context: "/proxy1",
     path: `http://localhost:${port1}`,
     target: `http://localhost:${port1}`,
   },
-};
+];
 
-const proxyWithString = {
-  "/proxy1": `http://localhost:${port1}`,
-};
+const proxyWithString = [
+  {
+    context: "/proxy1",
+    target: `http://localhost:${port1}`,
+  },
+];
 
-const proxyWithRouterAsObject = {
-  router: () => `http://localhost:${port1}`,
-};
+const proxyWithRouterAsObject = [
+  {
+    router: () => `http://localhost:${port1}`,
+  },
+];
 
 describe("proxy option", () => {
   let proxyServer1;
@@ -478,19 +492,21 @@ describe("proxy option", () => {
     let req;
     let listener;
 
-    const proxyTarget = {
-      target: `http://localhost:${port1}`,
-    };
-
     beforeAll(async () => {
       const compiler = webpack(config);
 
       server = new Server(
         {
-          proxy: {
-            "/proxy1": proxyTarget,
-            "/proxy2": proxyTarget,
-          },
+          proxy: [
+            {
+              context: "/proxy1",
+              target: `http://localhost:${port1}`,
+            },
+            {
+              context: "/proxy2",
+              target: `http://localhost:${port1}`,
+            },
+          ],
           port: port3,
         },
         compiler
@@ -605,18 +621,18 @@ describe("proxy option", () => {
     let server;
     let req;
     let listener;
-    const proxyTarget = {
-      target: `http://localhost:${port1}`,
-    };
 
     beforeAll(async () => {
       const compiler = webpack(config);
 
       server = new Server(
         {
-          proxy: {
-            "**": proxyTarget,
-          },
+          proxy: [
+            {
+              context: "**",
+              target: `http://localhost:${port1}`,
+            },
+          ],
           port: port3,
         },
         compiler
@@ -742,12 +758,12 @@ describe("proxy option", () => {
 
       server = new Server(
         {
-          proxy: {
-            "*": {
+          proxy: [
+            {
               context: () => true,
               target: `http://localhost:${port1}`,
             },
-          },
+          ],
           port: port3,
         },
         compiler
@@ -791,13 +807,14 @@ describe("proxy option", () => {
 
       server = new Server(
         {
-          proxy: {
-            "/my-path": {
+          proxy: [
+            {
+              context: "/my-path",
               target: "http://unknown:1234",
               logProvider: () => customLogProvider,
               logLevel: "error",
             },
-          },
+          ],
           port: port3,
         },
         compiler
@@ -842,13 +859,14 @@ describe("proxy option", () => {
 
       server = new Server(
         {
-          proxy: {
-            "/my-path": {
+          proxy: [
+            {
+              context: "my-path",
               target: "http://unknown:1234",
               logProvider: () => customLogProvider,
               logLevel: "silent",
             },
-          },
+          ],
           port: port3,
         },
         compiler
@@ -896,12 +914,13 @@ describe("proxy option", () => {
 
       server = new Server(
         {
-          proxy: {
-            "/my-path": {
+          proxy: [
+            {
+              context: "/my-path",
               target: "http://unknown:1234",
               logProvider: () => customLogProvider,
             },
-          },
+          ],
           port: port3,
         },
         compiler
@@ -949,12 +968,13 @@ describe("proxy option", () => {
 
       server = new Server(
         {
-          proxy: {
-            "/my-path": {
+          proxy: [
+            {
+              context: "/my-path",
               target: "http://unknown:1234",
               logProvider: () => customLogProvider,
             },
-          },
+          ],
           port: port3,
         },
         compiler
diff --git a/test/validate-options.test.js b/test/validate-options.test.js
index ca843c49d7..e9a7121c7f 100644
--- a/test/validate-options.test.js
+++ b/test/validate-options.test.js
@@ -239,11 +239,14 @@ const tests = {
           target: "http://localhost:3000",
         },
       ],
+    ],
+    failure: [
+      () => {},
+      false,
       {
         "/api": "http://localhost:3000",
       },
     ],
-    failure: [() => {}, false],
   },
   server: {
     success: [
diff --git a/types/lib/Server.d.ts b/types/lib/Server.d.ts
index 8ef1a038c9..7df37bad39 100644
--- a/types/lib/Server.d.ts
+++ b/types/lib/Server.d.ts
@@ -823,34 +823,25 @@ declare class Server {
         link: string;
       };
       Proxy: {
-        anyOf: (
-          | {
-              type: string;
-              items?: undefined;
-            }
-          | {
-              type: string;
-              items: {
-                anyOf: (
-                  | {
-                      type: string;
-                      instanceof?: undefined;
-                    }
-                  | {
-                      instanceof: string;
-                      type?: undefined;
-                    }
-                )[];
-              };
-            }
-        )[];
+        type: string;
+        items: {
+          anyOf: (
+            | {
+                type: string;
+                instanceof?: undefined;
+              }
+            | {
+                instanceof: string;
+                type?: undefined;
+              }
+          )[];
+        };
         description: string;
-        link: string /** @type {ClientConfiguration} */;
+        link: string;
       };
-      /** @type {ClientConfiguration} */
       Server: {
         anyOf: {
-          $ref: string;
+          $ref: string /** @type {WebSocketURL} */;
         }[];
         link: string;
         description: string;
@@ -859,6 +850,7 @@ declare class Server {
         enum: string[];
       };
       ServerEnum: {
+        /** @type {string} */
         enum: string[];
         cli: {
           exclude: boolean;
@@ -866,7 +858,7 @@ declare class Server {
       };
       ServerString: {
         type: string;
-        /** @type {ServerConfiguration} */ minLength: number;
+        minLength: number;
         cli: {
           exclude: boolean;
         };
@@ -881,13 +873,14 @@ declare class Server {
           };
           options: {
             $ref: string;
-          } /** @type {string} */;
+          };
         };
         additionalProperties: boolean;
       };
       ServerOptions: {
         type: string;
         additionalProperties: boolean;
+        /** @type {string} */
         properties: {
           passphrase: {
             type: string;
@@ -1106,7 +1099,7 @@ declare class Server {
             }
           | {
               $ref: string;
-              /** @type {MultiCompiler} */ type?: undefined;
+              type?: undefined;
               items?: undefined;
               cli?: undefined /** @typedef {import("express").Request} Request */;
             }
@@ -1121,7 +1114,7 @@ declare class Server {
           directory: {
             type: string;
             minLength: number;
-            /** @type {MultiCompiler} */ description: string;
+            description: string;
             link: string;
           };
           staticOptions: {
@@ -1162,6 +1155,10 @@ declare class Server {
                   cli?: undefined /** @typedef {import("express").Request} Request */;
                 }
             )[];
+            /**
+             * @param {WatchOptions & { aggregateTimeout?: number, ignored?: WatchOptions["ignored"], poll?: number | boolean }} watchOptions
+             * @returns {WatchOptions}
+             */
             description: string;
             link: string;
           };