diff --git a/core/src/main/java/io/grpc/internal/ServerImpl.java b/core/src/main/java/io/grpc/internal/ServerImpl.java
index 471507eaee2..35b1a091787 100644
--- a/core/src/main/java/io/grpc/internal/ServerImpl.java
+++ b/core/src/main/java/io/grpc/internal/ServerImpl.java
@@ -498,7 +498,7 @@ private void streamCreatedInternal(
       final StatsTraceContext statsTraceCtx = Preconditions.checkNotNull(
           stream.statsTraceContext(), "statsTraceCtx not present from stream");
 
-      final Context.CancellableContext context = createContext(stream, headers, statsTraceCtx);
+      final Context.CancellableContext context = createContext(headers, statsTraceCtx);
       final Executor wrappedExecutor;
       // This is a performance optimization that avoids the synchronization and queuing overhead
       // that comes with SerializingExecutor.
@@ -553,8 +553,7 @@ private void runInternal() {
               context.cancel(null);
               return;
             }
-            listener =
-                startCall(stream, methodName, method, headers, context, statsTraceCtx, tag);
+            listener = startCall(stream, methodName, method, headers, context, statsTraceCtx, tag);
           } catch (RuntimeException e) {
             stream.close(Status.fromThrowable(e), new Metadata());
             context.cancel(null);
@@ -566,6 +565,23 @@ private void runInternal() {
           } finally {
             jumpListener.setListener(listener);
           }
+
+          // An extremely short deadline may expire before stream.setListener(jumpListener).
+          // This causes NPE as in issue: https://github.com/grpc/grpc-java/issues/6300
+          // Delay of setting cancellationListener to context will fix the issue.
+          final class ServerStreamCancellationListener implements Context.CancellationListener {
+            @Override
+            public void cancelled(Context context) {
+              Status status = statusFromCancelled(context);
+              if (DEADLINE_EXCEEDED.getCode().equals(status.getCode())) {
+                // This should rarely get run, since the client will likely cancel the stream
+                // before the timeout is reached.
+                stream.cancel(status);
+              }
+            }
+          }
+
+          context.addListener(new ServerStreamCancellationListener(), directExecutor());
         }
       }
 
@@ -573,7 +589,7 @@ private void runInternal() {
     }
 
     private Context.CancellableContext createContext(
-        final ServerStream stream, Metadata headers, StatsTraceContext statsTraceCtx) {
+        Metadata headers, StatsTraceContext statsTraceCtx) {
       Long timeoutNanos = headers.get(TIMEOUT_KEY);
 
       Context baseContext = statsTraceCtx.serverFilterContext(rootContext);
@@ -586,19 +602,6 @@ private Context.CancellableContext createContext(
           baseContext.withDeadline(
               Deadline.after(timeoutNanos, NANOSECONDS, ticker),
               transport.getScheduledExecutorService());
-      final class ServerStreamCancellationListener implements Context.CancellationListener {
-        @Override
-        public void cancelled(Context context) {
-          Status status = statusFromCancelled(context);
-          if (DEADLINE_EXCEEDED.getCode().equals(status.getCode())) {
-            // This should rarely get run, since the client will likely cancel the stream before
-            // the timeout is reached.
-            stream.cancel(status);
-          }
-        }
-      }
-
-      context.addListener(new ServerStreamCancellationListener(), directExecutor());
 
       return context;
     }
diff --git a/core/src/test/java/io/grpc/internal/ServerImplTest.java b/core/src/test/java/io/grpc/internal/ServerImplTest.java
index 1a79f93ee3a..d2011f9541b 100644
--- a/core/src/test/java/io/grpc/internal/ServerImplTest.java
+++ b/core/src/test/java/io/grpc/internal/ServerImplTest.java
@@ -36,6 +36,7 @@
 import static org.mockito.ArgumentMatchers.same;
 import static org.mockito.Mockito.atLeast;
 import static org.mockito.Mockito.doThrow;
+import static org.mockito.Mockito.inOrder;
 import static org.mockito.Mockito.mock;
 import static org.mockito.Mockito.never;
 import static org.mockito.Mockito.times;
@@ -109,6 +110,7 @@
 import org.mockito.ArgumentCaptor;
 import org.mockito.ArgumentMatchers;
 import org.mockito.Captor;
+import org.mockito.InOrder;
 import org.mockito.Mock;
 import org.mockito.MockitoAnnotations;
 
@@ -1030,12 +1032,31 @@ public ServerCall.Listener<String> startCall(
     return streamListener;
   }
 
+  @Test
+  public void testContextExpiredBeforeStreamCreate_StreamCancelNotCalledBeforeSetListener()
+      throws Exception {
+    AtomicBoolean contextCancelled = new AtomicBoolean(false);
+    AtomicReference<Context> context = new AtomicReference<>();
+    AtomicReference<ServerCall<String, Integer>> callReference = new AtomicReference<>();
+
+    testStreamClose_setup(callReference, context, contextCancelled, 0L);
+
+    // This assert that stream.setListener(jumpListener) is called before stream.cancel(), which
+    // prevents extremely short deadlines causing NPEs.
+    InOrder inOrder = inOrder(stream);
+    inOrder.verify(stream).setListener(any(ServerStreamListener.class));
+    inOrder.verify(stream).cancel(statusCaptor.capture());
+
+    assertThat(statusCaptor.getValue().asException())
+        .hasMessageThat().contains("context timed out");
+    assertTrue(callReference.get().isCancelled());
+  }
+
   @Test
   public void testStreamClose_clientCancelTriggersImmediateCancellation() throws Exception {
     AtomicBoolean contextCancelled = new AtomicBoolean(false);
     AtomicReference<Context> context = new AtomicReference<>();
-    AtomicReference<ServerCall<String, Integer>> callReference
-        = new AtomicReference<>();
+    AtomicReference<ServerCall<String, Integer>> callReference = new AtomicReference<>();
 
     ServerStreamListener streamListener = testStreamClose_setup(callReference,
         context, contextCancelled, null);
@@ -1057,8 +1078,7 @@ public void testStreamClose_clientCancelTriggersImmediateCancellation() throws E
   public void testStreamClose_clientOkTriggersDelayedCancellation() throws Exception {
     AtomicBoolean contextCancelled = new AtomicBoolean(false);
     AtomicReference<Context> context = new AtomicReference<>();
-    AtomicReference<ServerCall<String, Integer>> callReference
-        = new AtomicReference<>();
+    AtomicReference<ServerCall<String, Integer>> callReference = new AtomicReference<>();
 
     ServerStreamListener streamListener = testStreamClose_setup(callReference,
         context, contextCancelled, null);
@@ -1081,8 +1101,7 @@ public void testStreamClose_clientOkTriggersDelayedCancellation() throws Excepti
   public void testStreamClose_deadlineExceededTriggersImmediateCancellation() throws Exception {
     AtomicBoolean contextCancelled = new AtomicBoolean(false);
     AtomicReference<Context> context = new AtomicReference<>();
-    AtomicReference<ServerCall<String, Integer>> callReference
-        = new AtomicReference<>();
+    AtomicReference<ServerCall<String, Integer>> callReference = new AtomicReference<>();
 
     testStreamClose_setup(callReference, context, contextCancelled, 50L);