diff --git a/okhttp-tests/src/test/java/okhttp3/WholeOperationTimeoutTest.java b/okhttp-tests/src/test/java/okhttp3/WholeOperationTimeoutTest.java
index 603f22139..5947b7ddd 100644
--- a/okhttp-tests/src/test/java/okhttp3/WholeOperationTimeoutTest.java
+++ b/okhttp-tests/src/test/java/okhttp3/WholeOperationTimeoutTest.java
@@ -24,6 +24,7 @@ import java.util.concurrent.atomic.AtomicReference;
 import okhttp3.mockwebserver.MockResponse;
 import okhttp3.mockwebserver.MockWebServer;
 import okio.BufferedSink;
+import org.junit.Ignore;
 import org.junit.Rule;
 import org.junit.Test;
 
@@ -256,6 +257,31 @@ public final class WholeOperationTimeoutTest {
     }
   }
 
+  @Ignore(
+      "timeout.exit() is called when the first connection is released but timeout.enter() is not called again")
+  @Test
+  public void timeoutFollowingRedirectOnNewConnection() throws Exception {
+    MockWebServer otherServer = new MockWebServer();
+
+    server.enqueue(
+        new MockResponse()
+            .setResponseCode(HttpURLConnection.HTTP_MOVED_TEMP)
+            .setHeader("Location", otherServer.url("/")));
+
+    otherServer.enqueue(new MockResponse().setHeadersDelay(500, TimeUnit.MILLISECONDS));
+
+    Request request = new Request.Builder().url(server.url("/")).build();
+
+    Call call = client.newCall(request);
+    call.timeout().timeout(250, TimeUnit.MILLISECONDS);
+    try {
+      Response response = call.execute();
+      fail();
+    } catch (IOException e) {
+      assertTrue(call.isCanceled());
+    }
+  }
+
   @Test public void noTimeout() throws Exception {
     server.enqueue(new MockResponse()
         .setHeadersDelay(250, TimeUnit.MILLISECONDS)