diff --git a/lib/Server.js b/lib/Server.js
index 41cbe3f654..cb7da1a6de 100644
--- a/lib/Server.js
+++ b/lib/Server.js
@@ -2242,6 +2242,21 @@ class Server {
         ),
       });
 
+      // Sync originalUrl with the rewritten url so that webpack-dev-middleware
+      // (which reads originalUrl) can serve the correct file after the rewrite.
+      middlewares.push({
+        name: "connect-history-api-fallback-url-sync",
+        /**
+         * @param {Request} req request
+         * @param {Response} res response
+         * @param {NextFunction} next next function
+         */
+        middleware: (req, res, next) => {
+          req.originalUrl = req.url;
+          next();
+        },
+      });
+
       // include our middleware to ensure
       // it is able to handle '/index.html' request after redirect
       middlewares.push({
diff --git a/package-lock.json b/package-lock.json
index 53d6db2a54..c56ba32934 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -31,7 +31,7 @@
         "schema-utils": "^4.2.0",
         "selfsigned": "^5.5.0",
         "serve-index": "^1.9.1",
-        "webpack-dev-middleware": "^7.4.5",
+        "webpack-dev-middleware": "^8.0.2",
         "ws": "^8.18.0"
       },
       "bin": {
@@ -4255,6 +4255,285 @@
         "tslib": "2"
       }
     },
+    "node_modules/@jsonjoy.com/fs-core": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-core/-/fs-core-4.57.1.tgz",
+      "integrity": "sha512-YrEi/ZPmgc+GfdO0esBF04qv8boK9Dg9WpRQw/+vM8Qt3nnVIJWIa8HwZ/LXVZ0DB11XUROM8El/7yYTJX+WtA==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/fs-node-builtins": "4.57.1",
+        "@jsonjoy.com/fs-node-utils": "4.57.1",
+        "thingies": "^2.5.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-fsa": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-fsa/-/fs-fsa-4.57.1.tgz",
+      "integrity": "sha512-ooEPvSW/HQDivPDPZMibHGKZf/QS4WRir1czGZmXmp3MsQqLECZEpN0JobrD8iV9BzsuwdIv+PxtWX9WpPLsIA==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/fs-core": "4.57.1",
+        "@jsonjoy.com/fs-node-builtins": "4.57.1",
+        "@jsonjoy.com/fs-node-utils": "4.57.1",
+        "thingies": "^2.5.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-node": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-node/-/fs-node-4.57.1.tgz",
+      "integrity": "sha512-3YaKhP8gXEKN+2O49GLNfNb5l2gbnCFHyAaybbA2JkkbQP3dpdef7WcUaHAulg/c5Dg4VncHsA3NWAUSZMR5KQ==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/fs-core": "4.57.1",
+        "@jsonjoy.com/fs-node-builtins": "4.57.1",
+        "@jsonjoy.com/fs-node-utils": "4.57.1",
+        "@jsonjoy.com/fs-print": "4.57.1",
+        "@jsonjoy.com/fs-snapshot": "4.57.1",
+        "glob-to-regex.js": "^1.0.0",
+        "thingies": "^2.5.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-node-builtins": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-node-builtins/-/fs-node-builtins-4.57.1.tgz",
+      "integrity": "sha512-XHkFKQ5GSH3uxm8c3ZYXVrexGdscpWKIcMWKFQpMpMJc8gA3AwOMBJXJlgpdJqmrhPyQXxaY9nbkNeYpacC0Og==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-node-to-fsa": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-node-to-fsa/-/fs-node-to-fsa-4.57.1.tgz",
+      "integrity": "sha512-pqGHyWWzNck4jRfaGV39hkqpY5QjRUQ/nRbNT7FYbBa0xf4bDG+TE1Gt2KWZrSkrkZZDE3qZUjYMbjwSliX6pg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/fs-fsa": "4.57.1",
+        "@jsonjoy.com/fs-node-builtins": "4.57.1",
+        "@jsonjoy.com/fs-node-utils": "4.57.1"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-node-utils": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-node-utils/-/fs-node-utils-4.57.1.tgz",
+      "integrity": "sha512-vp+7ZzIB8v43G+GLXTS4oDUSQmhAsRz532QmmWBbdYA20s465JvwhkSFvX9cVTqRRAQg+vZ7zWDaIEh0lFe2gw==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/fs-node-builtins": "4.57.1"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-print": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-print/-/fs-print-4.57.1.tgz",
+      "integrity": "sha512-Ynct7ZJmfk6qoXDOKfpovNA36ITUx8rChLmRQtW08J73VOiuNsU8PB6d/Xs7fxJC2ohWR3a5AqyjmLojfrw5yw==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/fs-node-utils": "4.57.1",
+        "tree-dump": "^1.1.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot": {
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/fs-snapshot/-/fs-snapshot-4.57.1.tgz",
+      "integrity": "sha512-/oG8xBNFMbDXTq9J7vepSA1kerS5vpgd3p5QZSPd+nX59uwodGJftI51gDYyHRpP57P3WCQf7LHtBYPqwUg2Bg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/buffers": "^17.65.0",
+        "@jsonjoy.com/fs-node-utils": "4.57.1",
+        "@jsonjoy.com/json-pack": "^17.65.0",
+        "@jsonjoy.com/util": "^17.65.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot/node_modules/@jsonjoy.com/base64": {
+      "version": "17.67.0",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/base64/-/base64-17.67.0.tgz",
+      "integrity": "sha512-5SEsJGsm15aP8TQGkDfJvz9axgPwAEm98S5DxOuYe8e1EbfajcDmgeXXzccEjh+mLnjqEKrkBdjHWS5vFNwDdw==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot/node_modules/@jsonjoy.com/buffers": {
+      "version": "17.67.0",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/buffers/-/buffers-17.67.0.tgz",
+      "integrity": "sha512-tfExRpYxBvi32vPs9ZHaTjSP4fHAfzSmcahOfNxtvGHcyJel+aibkPlGeBB+7AoC6hL7lXIE++8okecBxx7lcw==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot/node_modules/@jsonjoy.com/codegen": {
+      "version": "17.67.0",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/codegen/-/codegen-17.67.0.tgz",
+      "integrity": "sha512-idnkUplROpdBOV0HMcwhsCUS5TRUi9poagdGs70A6S4ux9+/aPuKbh8+UYRTLYQHtXvAdNfQWXDqZEx5k4Dj2Q==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot/node_modules/@jsonjoy.com/json-pack": {
+      "version": "17.67.0",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/json-pack/-/json-pack-17.67.0.tgz",
+      "integrity": "sha512-t0ejURcGaZsn1ClbJ/3kFqSOjlryd92eQY465IYrezsXmPcfHPE/av4twRSxf6WE+TkZgLY+71vCZbiIiFKA/w==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/base64": "17.67.0",
+        "@jsonjoy.com/buffers": "17.67.0",
+        "@jsonjoy.com/codegen": "17.67.0",
+        "@jsonjoy.com/json-pointer": "17.67.0",
+        "@jsonjoy.com/util": "17.67.0",
+        "hyperdyperid": "^1.2.0",
+        "thingies": "^2.5.0",
+        "tree-dump": "^1.1.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot/node_modules/@jsonjoy.com/json-pointer": {
+      "version": "17.67.0",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/json-pointer/-/json-pointer-17.67.0.tgz",
+      "integrity": "sha512-+iqOFInH+QZGmSuaybBUNdh7yvNrXvqR+h3wjXm0N/3JK1EyyFAeGJvqnmQL61d1ARLlk/wJdFKSL+LHJ1eaUA==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/util": "17.67.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
+    "node_modules/@jsonjoy.com/fs-snapshot/node_modules/@jsonjoy.com/util": {
+      "version": "17.67.0",
+      "resolved": "https://registry.npmjs.org/@jsonjoy.com/util/-/util-17.67.0.tgz",
+      "integrity": "sha512-6+8xBaz1rLSohlGh68D1pdw3AwDi9xydm8QNlAFkvnavCJYSze+pxoW2VKP8p308jtlMRLs5NTHfPlZLd4w7ew==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@jsonjoy.com/buffers": "17.67.0",
+        "@jsonjoy.com/codegen": "17.67.0"
+      },
+      "engines": {
+        "node": ">=10.0"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
+      }
+    },
     "node_modules/@jsonjoy.com/json-pack": {
       "version": "1.11.0",
       "resolved": "https://registry.npmjs.org/@jsonjoy.com/json-pack/-/json-pack-1.11.0.tgz",
@@ -7555,6 +7834,7 @@
       "version": "2.0.20",
       "resolved": "https://registry.npmjs.org/colorette/-/colorette-2.0.20.tgz",
       "integrity": "sha512-IfEDxwoWIjkeXL1eXcDiow4UbKjhLdq6/EuSVR9GMN7KVH3r9gQ83e73hsz1Nd1T3ijd5xv1wcWRYO+D6kCI2w==",
+      "dev": true,
       "license": "MIT"
     },
     "node_modules/combined-stream": {
@@ -17367,11 +17647,19 @@
       }
     },
     "node_modules/memfs": {
-      "version": "4.51.0",
-      "resolved": "https://registry.npmjs.org/memfs/-/memfs-4.51.0.tgz",
-      "integrity": "sha512-4zngfkVM/GpIhC8YazOsM6E8hoB33NP0BCESPOA6z7qaL6umPJNqkO8CNYaLV2FB2MV6H1O3x2luHHOSqppv+A==",
+      "version": "4.57.1",
+      "resolved": "https://registry.npmjs.org/memfs/-/memfs-4.57.1.tgz",
+      "integrity": "sha512-WvzrWPwMQT+PtbX2Et64R4qXKK0fj/8pO85MrUCzymX3twwCiJCdvntW3HdhG1teLJcHDDLIKx5+c3HckWYZtQ==",
       "license": "Apache-2.0",
       "dependencies": {
+        "@jsonjoy.com/fs-core": "4.57.1",
+        "@jsonjoy.com/fs-fsa": "4.57.1",
+        "@jsonjoy.com/fs-node": "4.57.1",
+        "@jsonjoy.com/fs-node-builtins": "4.57.1",
+        "@jsonjoy.com/fs-node-to-fsa": "4.57.1",
+        "@jsonjoy.com/fs-node-utils": "4.57.1",
+        "@jsonjoy.com/fs-print": "4.57.1",
+        "@jsonjoy.com/fs-snapshot": "4.57.1",
         "@jsonjoy.com/json-pack": "^1.11.0",
         "@jsonjoy.com/util": "^1.9.0",
         "glob-to-regex.js": "^1.0.1",
@@ -17382,6 +17670,9 @@
       "funding": {
         "type": "github",
         "url": "https://github.com/sponsors/streamich"
+      },
+      "peerDependencies": {
+        "tslib": "2"
       }
     },
     "node_modules/memorystream": {
@@ -23203,27 +23494,26 @@
       }
     },
     "node_modules/webpack-dev-middleware": {
-      "version": "7.4.5",
-      "resolved": "https://registry.npmjs.org/webpack-dev-middleware/-/webpack-dev-middleware-7.4.5.tgz",
-      "integrity": "sha512-uxQ6YqGdE4hgDKNf7hUiPXOdtkXvBJXrfEGYSx7P7LC8hnUYGK70X6xQXUvXeNyBDDcsiQXpG2m3G9vxowaEuA==",
+      "version": "8.0.2",
+      "resolved": "https://registry.npmjs.org/webpack-dev-middleware/-/webpack-dev-middleware-8.0.2.tgz",
+      "integrity": "sha512-MCBgoI025uJEcIYDT+R3mXUnhZA/GAxqwngADOwmHxMhQUgDztGow6AmyeEfI8L9KG2pDVg2kU6vjFnbCBH5Pg==",
       "license": "MIT",
       "dependencies": {
-        "colorette": "^2.0.10",
-        "memfs": "^4.43.1",
-        "mime-types": "^3.0.1",
+        "memfs": "^4.56.10",
+        "mime-types": "^3.0.2",
         "on-finished": "^2.4.1",
         "range-parser": "^1.2.1",
-        "schema-utils": "^4.0.0"
+        "schema-utils": "^4.3.3"
       },
       "engines": {
-        "node": ">= 18.12.0"
+        "node": ">= 20.9.0"
       },
       "funding": {
         "type": "opencollective",
         "url": "https://opencollective.com/webpack"
       },
       "peerDependencies": {
-        "webpack": "^5.0.0"
+        "webpack": "^5.101.0"
       },
       "peerDependenciesMeta": {
         "webpack": {
@@ -23232,15 +23522,19 @@
       }
     },
     "node_modules/webpack-dev-middleware/node_modules/mime-types": {
-      "version": "3.0.1",
-      "resolved": "https://registry.npmjs.org/mime-types/-/mime-types-3.0.1.tgz",
-      "integrity": "sha512-xRc4oEhT6eaBpU1XF7AjpOFD+xQmXNB5OVKwp4tqCuBpHLS/ZbBDrc07mYTDqVMg6PfxUjjNp85O6Cd2Z/5HWA==",
+      "version": "3.0.2",
+      "resolved": "https://registry.npmjs.org/mime-types/-/mime-types-3.0.2.tgz",
+      "integrity": "sha512-Lbgzdk0h4juoQ9fCKXW4by0UJqj+nOOrI9MJ1sSj4nI8aI2eo1qmvQEie4VD1glsS250n15LsWsYtCugiStS5A==",
       "license": "MIT",
       "dependencies": {
         "mime-db": "^1.54.0"
       },
       "engines": {
-        "node": ">= 0.6"
+        "node": ">=18"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/express"
       }
     },
     "node_modules/webpack-merge": {
diff --git a/package.json b/package.json
index 265269b6c7..d8d40f5b7e 100644
--- a/package.json
+++ b/package.json
@@ -66,7 +66,7 @@
     "schema-utils": "^4.2.0",
     "selfsigned": "^5.5.0",
     "serve-index": "^1.9.1",
-    "webpack-dev-middleware": "^7.4.5",
+    "webpack-dev-middleware": "^8.0.2",
     "ws": "^8.18.0"
   },
   "devDependencies": {