diff --git a/okhttp-testing-support/src/jvmMain/kotlin/okhttp3/OkHttpClientTestRule.kt b/okhttp-testing-support/src/jvmMain/kotlin/okhttp3/OkHttpClientTestRule.kt
index d5df9acae272..811b6e19645f 100644
--- a/okhttp-testing-support/src/jvmMain/kotlin/okhttp3/OkHttpClientTestRule.kt
+++ b/okhttp-testing-support/src/jvmMain/kotlin/okhttp3/OkHttpClientTestRule.kt
@@ -190,7 +190,9 @@ class OkHttpClientTestRule : BeforeEachCallback, AfterEachCallback {
         println("After delay: " + connectionPool.connectionCount())
       }
 
-      assertEquals(0, connectionPool.connectionCount())
+      assertEquals(0, connectionPool.connectionCount()) {
+        "Still ${connectionPool.connectionCount()} connections open"
+      }
     }
   }
 
diff --git a/okhttp/src/jvmMain/kotlin/okhttp3/internal/ws/RealWebSocket.kt b/okhttp/src/jvmMain/kotlin/okhttp3/internal/ws/RealWebSocket.kt
index 7934222ff008..f048f8488c56 100644
--- a/okhttp/src/jvmMain/kotlin/okhttp3/internal/ws/RealWebSocket.kt
+++ b/okhttp/src/jvmMain/kotlin/okhttp3/internal/ws/RealWebSocket.kt
@@ -170,9 +170,9 @@ class RealWebSocket(
           checkUpgradeSuccess(response, exchange)
           streams = exchange!!.newWebSocketStreams()
         } catch (e: IOException) {
-          exchange?.webSocketUpgradeFailed()
           failWebSocket(e, response)
           response.closeQuietly()
+          exchange?.webSocketUpgradeFailed()
           return
         }
 
diff --git a/okhttp/src/jvmTest/java/okhttp3/internal/ws/WebSocketHttpTest.java b/okhttp/src/jvmTest/java/okhttp3/internal/ws/WebSocketHttpTest.java
index 01f1f3f77b8c..3f7eef947bf3 100644
--- a/okhttp/src/jvmTest/java/okhttp3/internal/ws/WebSocketHttpTest.java
+++ b/okhttp/src/jvmTest/java/okhttp3/internal/ws/WebSocketHttpTest.java
@@ -22,6 +22,8 @@
 import java.net.ProtocolException;
 import java.net.SocketTimeoutException;
 import java.time.Duration;
+import java.util.ArrayList;
+import java.util.List;
 import java.util.Random;
 import java.util.concurrent.CountDownLatch;
 import java.util.concurrent.TimeUnit;
@@ -33,6 +35,7 @@
 import mockwebserver3.SocketPolicy;
 import mockwebserver3.SocketPolicy.KeepOpen;
 import mockwebserver3.SocketPolicy.NoResponse;
+import okhttp3.ConnectionPool;
 import okhttp3.OkHttpClient;
 import okhttp3.OkHttpClientTestRule;
 import okhttp3.Protocol;
@@ -351,10 +354,16 @@ private OkHttpClientTestRule configureClientTestRule() {
         .setHeader("Upgrade", "websocket")
         .setHeader("Sec-WebSocket-Accept", "ujmZX4KXZqjwy6vi1aQFH5p4Ygk=")
         .build());
-    newWebSocket();
+    webServer.enqueue(new MockResponse.Builder()
+            .socketPolicy(SocketPolicy.DisconnectAtStart.INSTANCE)
+            .build());
+
+    RealWebSocket webSocket = newWebSocket();
 
     clientListener.assertFailure(101, null, ProtocolException.class,
         "Expected 'Connection' header value 'Upgrade' but was 'null'");
+
+    webSocket.cancel();
   }
 
   @Test public void wrongConnectionHeader() throws IOException {
@@ -364,10 +373,16 @@ private OkHttpClientTestRule configureClientTestRule() {
         .setHeader("Connection", "Downgrade")
         .setHeader("Sec-WebSocket-Accept", "ujmZX4KXZqjwy6vi1aQFH5p4Ygk=")
         .build());
-    newWebSocket();
+    webServer.enqueue(new MockResponse.Builder()
+            .socketPolicy(SocketPolicy.DisconnectAtStart.INSTANCE)
+            .build());
+
+    RealWebSocket webSocket = newWebSocket();
 
     clientListener.assertFailure(101, null, ProtocolException.class,
         "Expected 'Connection' header value 'Upgrade' but was 'Downgrade'");
+
+    webSocket.cancel();
   }
 
   @Test public void missingUpgradeHeader() throws IOException {
@@ -376,10 +391,16 @@ private OkHttpClientTestRule configureClientTestRule() {
         .setHeader("Connection", "Upgrade")
         .setHeader("Sec-WebSocket-Accept", "ujmZX4KXZqjwy6vi1aQFH5p4Ygk=")
         .build());
-    newWebSocket();
+    webServer.enqueue(new MockResponse.Builder()
+            .socketPolicy(SocketPolicy.DisconnectAtStart.INSTANCE)
+            .build());
+
+    RealWebSocket webSocket = newWebSocket();
 
     clientListener.assertFailure(101, null, ProtocolException.class,
         "Expected 'Upgrade' header value 'websocket' but was 'null'");
+
+    webSocket.cancel();
   }
 
   @Test public void wrongUpgradeHeader() throws IOException {
@@ -389,10 +410,16 @@ private OkHttpClientTestRule configureClientTestRule() {
         .setHeader("Upgrade", "Pepsi")
         .setHeader("Sec-WebSocket-Accept", "ujmZX4KXZqjwy6vi1aQFH5p4Ygk=")
         .build());
-    newWebSocket();
+    webServer.enqueue(new MockResponse.Builder()
+            .socketPolicy(SocketPolicy.DisconnectAtStart.INSTANCE)
+            .build());
+
+    RealWebSocket webSocket = newWebSocket();
 
     clientListener.assertFailure(101, null, ProtocolException.class,
         "Expected 'Upgrade' header value 'websocket' but was 'Pepsi'");
+
+    webSocket.cancel();
   }
 
   @Test public void missingMagicHeader() throws IOException {
@@ -401,10 +428,16 @@ private OkHttpClientTestRule configureClientTestRule() {
         .setHeader("Connection", "Upgrade")
         .setHeader("Upgrade", "websocket")
         .build());
-    newWebSocket();
+    webServer.enqueue(new MockResponse.Builder()
+            .socketPolicy(SocketPolicy.DisconnectAtStart.INSTANCE)
+            .build());
+
+    RealWebSocket webSocket = newWebSocket();
 
     clientListener.assertFailure(101, null, ProtocolException.class,
         "Expected 'Sec-WebSocket-Accept' header value 'ujmZX4KXZqjwy6vi1aQFH5p4Ygk=' but was 'null'");
+
+    webSocket.cancel();
   }
 
   @Test public void wrongMagicHeader() throws IOException {
@@ -414,10 +447,16 @@ private OkHttpClientTestRule configureClientTestRule() {
         .setHeader("Upgrade", "websocket")
         .setHeader("Sec-WebSocket-Accept", "magic")
         .build());
-    newWebSocket();
+    webServer.enqueue(new MockResponse.Builder()
+            .socketPolicy(SocketPolicy.DisconnectAtStart.INSTANCE)
+            .build());
+
+    RealWebSocket webSocket = newWebSocket();
 
     clientListener.assertFailure(101, null, ProtocolException.class,
         "Expected 'Sec-WebSocket-Accept' header value 'ujmZX4KXZqjwy6vi1aQFH5p4Ygk=' but was 'magic'");
+
+    webSocket.cancel();
   }
 
   @Test public void clientIncludesForbiddenHeader() throws IOException {
@@ -868,6 +907,53 @@ private OkHttpClientTestRule configureClientTestRule() {
     webSocket.close(1000, null);
   }
 
+  /** https://github.com/square/okhttp/issues/7768 */
+  @Test public void reconnectingToNonWebSocket() throws InterruptedException {
+    // Async test is problematic
+    client = this.client.newBuilder()
+            .connectionPool(new ConnectionPool())
+            .build();
+
+    for (int i = 0; i < 30; i++) {
+      webServer.enqueue(new MockResponse.Builder()
+        .bodyDelay(100, TimeUnit.MILLISECONDS)
+        .body("Wrong endpoint")
+        .code(401)
+        .build());
+    }
+
+    Request request = new Request.Builder()
+      .url(webServer.url("/"))
+      .build();
+
+    CountDownLatch attempts = new CountDownLatch(20);
+
+    List<WebSocket> webSockets = new ArrayList<>();
+
+    WebSocketListener reconnectOnFailure = new WebSocketListener() {
+      @Override
+      public void onFailure(WebSocket webSocket, Throwable t, Response response) {
+        if (attempts.getCount() > 0) {
+          clientListener.setNextEventDelegate(this);
+          webSockets.add(client.newWebSocket(request, clientListener));
+          attempts.countDown();
+        }
+      }
+    };
+
+    clientListener.setNextEventDelegate(reconnectOnFailure);
+
+    webSockets.add(client.newWebSocket(request, clientListener));
+
+    attempts.await();
+
+    for (WebSocket webSocket: webSockets) {
+      webSocket.cancel();
+    }
+    client.dispatcher().cancelAll();
+    client.connectionPool().evictAll();
+  }
+
   @Test public void compressedMessages() throws Exception {
     successfulExtensions("permessage-deflate");
   }