diff --git a/okhttp/src/main/java/okhttp3/internal/connection/ExchangeFinder.kt b/okhttp/src/main/java/okhttp3/internal/connection/ExchangeFinder.kt
index 2a7bec00a..3a35ae314 100644
--- a/okhttp/src/main/java/okhttp3/internal/connection/ExchangeFinder.kt
+++ b/okhttp/src/main/java/okhttp3/internal/connection/ExchangeFinder.kt
@@ -113,13 +113,23 @@ class ExchangeFinder(
           connectionRetryEnabled = connectionRetryEnabled
       )
 
-      // Confirm that the connection is good. If it isn't, take it out of the pool and start again.
-      if (!candidate.isHealthy(doExtensiveHealthChecks)) {
-        candidate.noNewExchanges()
-        continue
+      // Confirm that the connection is good.
+      if (candidate.isHealthy(doExtensiveHealthChecks)) {
+        return candidate
       }
 
-      return candidate
+      // If it isn't, take it out of the pool.
+      candidate.noNewExchanges()
+
+      // Make sure we have some routes left to try. One example where we may exhaust all the routes
+      // would happen if we made a new connection and it immediately is detected as unhealthy.
+      synchronized(connectionPool) {
+        val routesLeft = routeSelection?.hasNext() ?: true
+        val routesSelectionLeft = routeSelector?.hasNext() ?: true
+        if (nextRouteToTry == null && !routesLeft && !routesSelectionLeft) {
+          throw IOException("exhausted all routes")
+        }
+      }
     }
   }
 
diff --git a/okhttp/src/test/java/okhttp3/CallTest.java b/okhttp/src/test/java/okhttp3/CallTest.java
index 5f3e07a2f..767e7ef42 100644
--- a/okhttp/src/test/java/okhttp3/CallTest.java
+++ b/okhttp/src/test/java/okhttp3/CallTest.java
@@ -61,6 +61,7 @@ import okhttp3.CallEvent.ConnectionReleased;
 import okhttp3.CallEvent.ResponseFailed;
 import okhttp3.internal.DoubleInetAddressDns;
 import okhttp3.internal.RecordingOkAuthenticator;
+import okhttp3.internal.Util;
 import okhttp3.internal.Version;
 import okhttp3.internal.http.RecordingProxySelector;
 import okhttp3.internal.io.InMemoryFileSystem;
@@ -3792,6 +3793,20 @@ public final class CallTest {
     }
   }
 
+  @Test public void connectionIsImmediatelyUnhealthy() throws Exception {
+    EventListener listener = new EventListener() {
+      @Override public void connectionAcquired(Call call, Connection connection) {
+        Util.closeQuietly(connection.socket());
+      }
+    };
+
+    client = client.newBuilder()
+        .eventListener(listener)
+        .build();
+
+    executeSynchronously("/").assertFailure(IOException.class);
+  }
+
   @Test public void requestBodyThrowsUnrelatedToNetwork() throws Exception {
     server.enqueue(new MockResponse());