diff --git a/.changeset/clean-icons-wonder.md b/.changeset/clean-icons-wonder.md
new file mode 100644
index 0000000000..b6beb58969
--- /dev/null
+++ b/.changeset/clean-icons-wonder.md
@@ -0,0 +1,5 @@
+---
+'@backstage/plugin-kubernetes-backend': patch
+---
+
+Handle Proxy WS upgrade manually for WS handshakes
diff --git a/plugins/kubernetes-backend/api-report.md b/plugins/kubernetes-backend/api-report.md
index 051706bbd5..158b917a48 100644
--- a/plugins/kubernetes-backend/api-report.md
+++ b/plugins/kubernetes-backend/api-report.md
@@ -18,7 +18,7 @@ import { Logger } from 'winston';
 import type { ObjectsByEntityResponse } from '@backstage/plugin-kubernetes-common';
 import { PermissionEvaluator } from '@backstage/plugin-permission-common';
 import { PluginEndpointDiscovery } from '@backstage/backend-common';
-import type { RequestHandler } from 'express';
+import { RequestHandler } from 'http-proxy-middleware';
 import { TokenCredential } from '@azure/identity';
 
 // @public (undocumented)
diff --git a/plugins/kubernetes-backend/package.json b/plugins/kubernetes-backend/package.json
index f755dc2c6b..17da706d66 100644
--- a/plugins/kubernetes-backend/package.json
+++ b/plugins/kubernetes-backend/package.json
@@ -68,6 +68,7 @@
     "@jest-mock/express": "^2.0.1",
     "@kubernetes/client-node": "0.18.1",
     "@types/express": "^4.17.6",
+    "@types/http-proxy-middleware": "^0.19.3",
     "@types/luxon": "^3.0.0",
     "compression": "^1.7.4",
     "cors": "^2.8.5",
@@ -88,8 +89,6 @@
     "@backstage/backend-test-utils": "workspace:^",
     "@backstage/cli": "workspace:^",
     "@types/aws4": "^1.5.1",
-    "@types/http-proxy-middleware": "^0.19.3",
-    "cross-fetch": "^3.1.5",
     "mock-fs": "^5.2.0",
     "msw": "^1.0.0",
     "supertest": "^6.1.3",
diff --git a/plugins/kubernetes-backend/src/service/KubernetesProxy.test.ts b/plugins/kubernetes-backend/src/service/KubernetesProxy.test.ts
index a84482082f..327d580d10 100644
--- a/plugins/kubernetes-backend/src/service/KubernetesProxy.test.ts
+++ b/plugins/kubernetes-backend/src/service/KubernetesProxy.test.ts
@@ -46,7 +46,6 @@ import {
   HEADER_KUBERNETES_CLUSTER,
   KubernetesProxy,
 } from './KubernetesProxy';
-import fetch from 'cross-fetch';
 
 import type { Request } from 'express';
 
@@ -757,7 +756,6 @@ describe('KubernetesProxy', () => {
 
       const wsProxyAddress = `ws://127.0.0.1:${proxyPort}${proxyPath}${wsPath}`;
       const wsAddress = `ws://localhost:${wsPort}${wsPath}`;
-      console.log('Ports: ', wsProxyAddress, wsAddress);
 
       // Let this request through so it reaches the express router above
       worker.use(
@@ -769,10 +767,6 @@ describe('KubernetesProxy', () => {
         ),
       );
 
-      // Prepopulate the proxy so the WebSocket upgrade can happen, result doesn't actually matter
-      const result = await fetch(wsProxyAddress.replace('ws', 'http'));
-      expect(result.ok).toBeFalsy();
-
       const webSocket = new WebSocket(wsProxyAddress);
 
       const connectMessagePromise = eventPromiseFactory(webSocket, 'message');
diff --git a/plugins/kubernetes-backend/src/service/KubernetesProxy.ts b/plugins/kubernetes-backend/src/service/KubernetesProxy.ts
index 6e699d1220..d2a3649c27 100644
--- a/plugins/kubernetes-backend/src/service/KubernetesProxy.ts
+++ b/plugins/kubernetes-backend/src/service/KubernetesProxy.ts
@@ -13,7 +13,6 @@
  * See the License for the specific language governing permissions and
  * limitations under the License.
  */
-
 import {
   ErrorResponseBody,
   ForwardedError,
@@ -24,16 +23,18 @@ import {
 import { getBearerTokenFromAuthorizationHeader } from '@backstage/plugin-auth-node';
 import { kubernetesProxyPermission } from '@backstage/plugin-kubernetes-common';
 import {
-  PermissionEvaluator,
   AuthorizeResult,
+  PermissionEvaluator,
 } from '@backstage/plugin-permission-common';
 import { bufferFromFileOrString } from '@kubernetes/client-node';
-import type { Request, RequestHandler } from 'express';
-import { createProxyMiddleware } from 'http-proxy-middleware';
+import { createProxyMiddleware, RequestHandler } from 'http-proxy-middleware';
 import { Logger } from 'winston';
+
 import { AuthenticationStrategy } from '../auth';
 import { ClusterDetails, KubernetesClustersSupplier } from '../types/types';
 
+import type { Request } from 'express';
+
 export const APPLICATION_JSON: string = 'application/json';
 
 /**
@@ -121,7 +122,17 @@ export class KubernetesProxy {
       }
 
       const middleware = await this.getMiddleware(req);
-      middleware(req, res, next);
+
+      // If req is an upgrade handshake, use middleware upgrade instead of http request handler https://github.com/chimurai/http-proxy-middleware#external-websocket-upgrade
+      if (
+        req.header('connection')?.toLowerCase() === 'upgrade' &&
+        req.header('upgrade')?.toLowerCase() === 'websocket'
+      ) {
+        // Missing the `head`, since it's optional we pass undefined to avoid type issues
+        middleware.upgrade!(req, req.socket, undefined);
+      } else {
+        middleware(req, res, next);
+      }
     };
   }
 
diff --git a/yarn.lock b/yarn.lock
index d0c50c3999..c08f5686f5 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -7643,7 +7643,6 @@ __metadata:
     "@types/luxon": ^3.0.0
     compression: ^1.7.4
     cors: ^2.8.5
-    cross-fetch: ^3.1.5
     express: ^4.17.1
     express-promise-router: ^4.1.0
     fs-extra: 10.1.0