diff --git a/okhttp/src/main/java/io/grpc/okhttp/OkHttpClientTransport.java b/okhttp/src/main/java/io/grpc/okhttp/OkHttpClientTransport.java
index 29d3dbc1cdf..2f6b836dc3a 100644
--- a/okhttp/src/main/java/io/grpc/okhttp/OkHttpClientTransport.java
+++ b/okhttp/src/main/java/io/grpc/okhttp/OkHttpClientTransport.java
@@ -83,9 +83,13 @@
 import java.util.Locale;
 import java.util.Map;
 import java.util.Random;
+import java.util.concurrent.BrokenBarrierException;
 import java.util.concurrent.CountDownLatch;
+import java.util.concurrent.CyclicBarrier;
 import java.util.concurrent.Executor;
 import java.util.concurrent.ScheduledExecutorService;
+import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
 import java.util.logging.Level;
 import java.util.logging.Logger;
 import javax.annotation.Nullable;
@@ -499,8 +503,15 @@ public Runnable start(Listener listener) {
       outboundFlow = new OutboundFlowController(this, frameWriter);
     }
     final CountDownLatch latch = new CountDownLatch(1);
+    final CountDownLatch latchForExtraThread = new CountDownLatch(1);
+    // The transport needs up to two threads to function once started,
+    // but only needs one during handshaking. Start another thread during handshaking
+    // to make sure there's still a free thread available. If the number of threads is exhausted,
+    // it is better to kill the transport than for all the transports to hang unable to send.
+    CyclicBarrier barrier = new CyclicBarrier(2);
     // Connecting in the serializingExecutor, so that some stream operations like synStream
     // will be executed after connected.
+
     serializingExecutor.execute(new Runnable() {
       @Override
       public void run() {
@@ -510,8 +521,14 @@ public void run() {
         // initial preface.
         try {
           latch.await();
+          barrier.await(1000, TimeUnit.MILLISECONDS);
         } catch (InterruptedException e) {
           Thread.currentThread().interrupt();
+        } catch (TimeoutException | BrokenBarrierException e) {
+          startGoAway(0, ErrorCode.INTERNAL_ERROR, Status.UNAVAILABLE
+              .withDescription("Timed out waiting for second handshake thread. "
+                + "The transport executor pool may have run out of threads"));
+          return;
         }
         // Use closed source on failure so that the reader immediately shuts down.
         BufferedSource source = Okio.buffer(new Source() {
@@ -575,6 +592,7 @@ sslSocketFactory, hostnameVerifier, sock, getOverridenHost(), getOverridenPort()
           return;
         } finally {
           clientFrameHandler = new ClientFrameHandler(variant.newReader(source, true));
+          latchForExtraThread.countDown();
         }
         synchronized (lock) {
           socket = Preconditions.checkNotNull(sock, "socket");
@@ -584,6 +602,21 @@ sslSocketFactory, hostnameVerifier, sock, getOverridenHost(), getOverridenPort()
         }
       }
     });
+
+    executor.execute(new Runnable() {
+      @Override
+      public void run() {
+        try {
+          barrier.await(1000, TimeUnit.MILLISECONDS);
+          latchForExtraThread.await();
+        } catch (BrokenBarrierException | TimeoutException e) {
+          // Something bad happened, maybe too few threads available!
+          // This will be handled in the handshake thread.
+        } catch (InterruptedException e) {
+          Thread.currentThread().interrupt();
+        }
+      }
+    });
     // Schedule to send connection preface & settings before any other write.
     try {
       sendConnectionPrefaceAndSettings();
diff --git a/okhttp/src/test/java/io/grpc/okhttp/OkHttpClientTransportTest.java b/okhttp/src/test/java/io/grpc/okhttp/OkHttpClientTransportTest.java
index 987cc09203e..daf5073992e 100644
--- a/okhttp/src/test/java/io/grpc/okhttp/OkHttpClientTransportTest.java
+++ b/okhttp/src/test/java/io/grpc/okhttp/OkHttpClientTransportTest.java
@@ -247,6 +247,28 @@ public void testToString() throws Exception {
     assertTrue("Unexpected: " + s, s.contains(address.toString()));
   }
 
+  @Test
+  public void testTransportExecutorWithTooFewThreads() throws Exception {
+    ExecutorService fixedPoolExecutor = Executors.newFixedThreadPool(1);
+    channelBuilder.transportExecutor(fixedPoolExecutor);
+    InetSocketAddress address = InetSocketAddress.createUnresolved("hostname", 31415);
+    clientTransport = new OkHttpClientTransport(
+        channelBuilder.buildTransportFactory(),
+        address,
+        "hostname",
+        null,
+        EAG_ATTRS,
+        NO_PROXY,
+        tooManyPingsRunnable);
+    clientTransport.start(transportListener);
+    ArgumentCaptor<Status> statusCaptor = ArgumentCaptor.forClass(Status.class);
+    verify(transportListener, timeout(TIME_OUT_MS)).transportShutdown(statusCaptor.capture());
+    Status capturedStatus = statusCaptor.getValue();
+    assertEquals("Timed out waiting for second handshake thread. "
+        + "The transport executor pool may have run out of threads",
+        capturedStatus.getDescription());
+  }
+
   /**
    * Test logging is functioning correctly for client received Http/2 frames. Not intended to test
    * actual frame content being logged.