diff --git a/ui/src/ui/gateway.node.test.ts b/ui/src/ui/gateway.node.test.ts
index a7312f71bb45..f51d8695bb8a 100644
--- a/ui/src/ui/gateway.node.test.ts
+++ b/ui/src/ui/gateway.node.test.ts
@@ -324,6 +324,46 @@ describe("GatewayBrowserClient", () => {
     vi.useRealTimers();
   });
 
+  it("reports generic WebSocket construction failures without retrying", async () => {
+    vi.useFakeTimers();
+    const onClose = vi.fn();
+    class ThrowingWebSocket {
+      static OPEN = 1;
+
+      constructor(_url: string) {
+        throw new TypeError("constructor failed");
+      }
+    }
+    vi.stubGlobal("WebSocket", ThrowingWebSocket);
+
+    const client = new GatewayBrowserClient({
+      url: "ws://gateway.example:18789",
+      token: "shared-auth-token",
+      onClose,
+    });
+
+    expect(() => client.start()).not.toThrow();
+    expect(onClose).toHaveBeenCalledWith({
+      code: 1006,
+      reason: "websocket error",
+      error: expect.objectContaining({
+        code: "BROWSER_WEBSOCKET_CONSTRUCTOR_ERROR",
+        message: expect.stringContaining("Could not create the Gateway WebSocket"),
+        details: expect.objectContaining({
+          code: "BROWSER_WEBSOCKET_CONSTRUCTOR_ERROR",
+          browserErrorName: "TypeError",
+          browserMessage: "constructor failed",
+        }),
+      }),
+    });
+    expect(wsInstances).toHaveLength(0);
+
+    await vi.advanceTimersByTimeAsync(30_000);
+    expect(onClose).toHaveBeenCalledTimes(1);
+
+    vi.useRealTimers();
+  });
+
   it("reports request timing for attributed RPC latency", async () => {
     const onRequestTiming = vi.fn();
     const client = new GatewayBrowserClient({
diff --git a/ui/src/ui/views/login-gate.test.ts b/ui/src/ui/views/login-gate.test.ts
index 219f2dcf5ee5..13212c78f6c2 100644
--- a/ui/src/ui/views/login-gate.test.ts
+++ b/ui/src/ui/views/login-gate.test.ts
@@ -115,6 +115,36 @@ describe("resolveLoginFailureFeedback", () => {
     expect(feedback?.steps.join(" ")).toContain("gateway.controlUi.allowInsecureAuth");
   });
 
+  it("explains browser WebSocket security failures as insecure context", () => {
+    const feedback = resolveLoginFailureFeedback({
+      connected: false,
+      lastError:
+        "Browser refused the Gateway WebSocket for security reasons. Use wss:// when the Control UI is served over HTTPS/Tailscale Serve, or open the loopback dashboard at http://127.0.0.1:18789.",
+      lastErrorCode: "BROWSER_WEBSOCKET_SECURITY_ERROR",
+      hasToken: true,
+      hasPassword: false,
+    });
+
+    expect(feedback?.kind).toBe("insecure-context");
+    expect(feedback?.rawError).toContain("Use wss://");
+    expect(feedback?.rawError).toContain("http://127.0.0.1:18789");
+    expect(feedback?.steps.join(" ")).toContain("Tailscale Serve");
+    expect(feedback?.steps.join(" ")).toContain("gateway.controlUi.allowInsecureAuth");
+  });
+
+  it("keeps generic browser WebSocket constructor failures on the network path", () => {
+    const feedback = resolveLoginFailureFeedback({
+      connected: false,
+      lastError: "Could not create the Gateway WebSocket: constructor failed",
+      lastErrorCode: "BROWSER_WEBSOCKET_CONSTRUCTOR_ERROR",
+      hasToken: false,
+      hasPassword: false,
+    });
+
+    expect(feedback?.kind).toBe("network");
+    expect(feedback?.steps.join(" ")).toContain("WebSocket URL");
+  });
+
   it("explains browser origin rejections", () => {
     const feedback = resolveLoginFailureFeedback({
       connected: false,
diff --git a/ui/src/ui/views/overview-hints.ts b/ui/src/ui/views/overview-hints.ts
index ecc184ef7f7d..d3f759c30da1 100644
--- a/ui/src/ui/views/overview-hints.ts
+++ b/ui/src/ui/views/overview-hints.ts
@@ -25,7 +25,10 @@ const AUTH_FAILURE_CODES = new Set<string>([
   ConnectErrorDetailCodes.AUTH_TAILSCALE_IDENTITY_MISMATCH,
 ]);
 
+const BROWSER_WEBSOCKET_SECURITY_ERROR_CODE = "BROWSER_WEBSOCKET_SECURITY_ERROR";
+
 const INSECURE_CONTEXT_CODES = new Set<string>([
+  BROWSER_WEBSOCKET_SECURITY_ERROR_CODE,
   ConnectErrorDetailCodes.CONTROL_UI_DEVICE_IDENTITY_REQUIRED,
   ConnectErrorDetailCodes.DEVICE_IDENTITY_REQUIRED,
 ]);
diff --git a/ui/src/ui/views/overview.node.test.ts b/ui/src/ui/views/overview.node.test.ts
index 33500d1dae63..a806ec56727b 100644
--- a/ui/src/ui/views/overview.node.test.ts
+++ b/ui/src/ui/views/overview.node.test.ts
@@ -4,6 +4,7 @@ import { ConnectErrorDetailCodes } from "../../../../src/gateway/protocol/connec
 import {
   resolveAuthHintKind,
   resolvePairingHint,
+  shouldShowInsecureContextHint,
   shouldShowPairingHint,
 } from "./overview-hints.ts";
 
@@ -107,3 +108,25 @@ describe("resolveAuthHintKind", () => {
     ).toBe("failed");
   });
 });
+
+describe("shouldShowInsecureContextHint", () => {
+  it("returns true for browser WebSocket security errors", () => {
+    expect(
+      shouldShowInsecureContextHint(
+        false,
+        "Browser refused the Gateway WebSocket for security reasons.",
+        "BROWSER_WEBSOCKET_SECURITY_ERROR",
+      ),
+    ).toBe(true);
+  });
+
+  it("does not treat generic WebSocket constructor errors as insecure context", () => {
+    expect(
+      shouldShowInsecureContextHint(
+        false,
+        "Could not create the Gateway WebSocket: constructor failed",
+        "BROWSER_WEBSOCKET_CONSTRUCTOR_ERROR",
+      ),
+    ).toBe(false);
+  });
+});