diff --git a/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java b/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java
index 3c8d3d07571..604ee5c6cd1 100644
--- a/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java
+++ b/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java
@@ -222,12 +222,25 @@ private void runOrBuffer(ActionItem actionItem) throws IOException {
       if (actionItem == completeAction) {
         return;
       }
-      if (!isReady.getAsBoolean()) {
+      if (actionItem != flushAction) {
+        // This is a writeBytes action. Always set readyAndDrained to false even when
+        // isReady() returns true. Tomcat requires onWritePossible() to fire between
+        // writes, even if isReady() is still true.
         boolean successful =
             writeState.compareAndSet(curState, curState.withReadyAndDrained(false));
         LockSupport.unpark(parkingThread);
         checkState(successful, "Bug: curState is unexpectedly changed by another thread");
         log.finest("the servlet output stream becomes not ready");
+      } else {
+        // For flush, only set to false if isReady() returns false.
+        // If isReady() is still true, keep readyAndDrained true so flush goes direct.
+        if (!isReady.getAsBoolean()) {
+          boolean successful =
+              writeState.compareAndSet(curState, curState.withReadyAndDrained(false));
+          LockSupport.unpark(parkingThread);
+          checkState(successful, "Bug: curState is unexpectedly changed by another thread");
+          log.finest("the servlet output stream becomes not ready");
+        }
       }
     } else { // buffer to the writeChain
       writeChain.offer(actionItem);
@@ -274,9 +287,10 @@ private static final class WriteState {
      * check of {@link javax.servlet.ServletOutputStream#isReady()} is true.
      *
      * <p>readyAndDrained turns from true to false when:
-     * {@code runOrBuffer()} exits while either the action item is written directly to the
-     * servlet output stream and the check of {@link javax.servlet.ServletOutputStream#isReady()}
-     * right after that returns false, or the action item is buffered into the writeChain.
+     * {@code runOrBuffer()} exits after writing directly to the servlet output stream.
+     * For writeBytes actions, it always transitions to false. For flush actions,
+     * it transitions to false only when {@link javax.servlet.ServletOutputStream#isReady()}
+     * returns false, or when the action is buffered into the writeChain.
      */
     final boolean readyAndDrained;
 
diff --git a/servlet/src/test/java/io/grpc/servlet/AsyncServletOutputStreamWriterTest.java b/servlet/src/test/java/io/grpc/servlet/AsyncServletOutputStreamWriterTest.java
new file mode 100644
index 00000000000..a967b22922c
--- /dev/null
+++ b/servlet/src/test/java/io/grpc/servlet/AsyncServletOutputStreamWriterTest.java
@@ -0,0 +1,132 @@
+/*
+ * Copyright 2026 The gRPC Authors
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package io.grpc.servlet;
+
+import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertTrue;
+
+import io.grpc.servlet.AsyncServletOutputStreamWriter.ActionItem;
+import io.grpc.servlet.AsyncServletOutputStreamWriter.Log;
+import java.io.IOException;
+import java.util.ArrayList;
+import java.util.List;
+import java.util.concurrent.atomic.AtomicBoolean;
+import java.util.function.BiFunction;
+import java.util.function.BooleanSupplier;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+import org.junit.runners.JUnit4;
+
+/**
+ * Unit test for {@link AsyncServletOutputStreamWriter} with a mock isReady supplier
+ * that always returns true. This specifically tests the scenario where isReady stays
+ * true across multiple write calls (as can happen with Tomcat and other servlet
+ * containers that defer onWritePossible until the previous write completes internally).
+ */
+@RunWith(JUnit4.class)
+public class AsyncServletOutputStreamWriterTest {
+
+  /**
+   * Test that multiple consecutive writes succeed even when isReady() always returns true.
+   * This reproduces the Tomcat issue where isReady() returns true but write() still fails
+   * because the previous write hasn't completed internally.
+   */
+  @Test
+  public void writeBytes_alwaysReady_doesNotStall() throws IOException {
+    AtomicBoolean isReady = new AtomicBoolean(true);
+    List<byte[]> writtenData = new ArrayList<>();
+
+    BiFunction<byte[], Integer, ActionItem> writeAction =
+        (bytes, numBytes) -> () -> {
+          writtenData.add(bytes);
+        };
+
+    ActionItem flushAction = () -> {};
+
+    ActionItem completeAction = () -> {};
+
+    BooleanSupplier isReadySupplier = () -> {
+      // Note: isReady stays true throughout this test
+      return isReady.get();
+    };
+
+    AsyncServletOutputStreamWriter writer =
+        new AsyncServletOutputStreamWriter(writeAction, flushAction, completeAction, isReadySupplier, new Log() {});
+
+    // Simulate the first onWritePossible call (container init)
+    isReady.set(true);
+    writer.onWritePossible();
+
+    // Write multiple times while isReady stays true
+    // Before the fix, writes would stall because isReady returned true
+    // but the previous write hadn't completed internally
+    for (int i = 0; i < 5; i++) {
+      byte[] data = new byte[]{(byte) i};
+      writer.writeBytes(data, 1);
+    }
+
+    // Verify all writes completed
+    assertEquals("All writes should complete", 5, writtenData.size());
+  }
+
+  /**
+   * Test that writeBytes with isReady returning false eventually triggers onWritePossible.
+   */
+  @Test
+  public void writeBytes_isReadyBecomesFalse_triggersOnWritePossible() throws IOException {
+    AtomicBoolean isReady = new AtomicBoolean(true);
+    List<String> actions = new ArrayList<>();
+
+    BiFunction<byte[], Integer, ActionItem> writeAction =
+        (bytes, numBytes) -> () -> {
+          actions.add("write");
+        };
+
+    ActionItem flushAction = () -> {
+      actions.add("flush");
+    };
+
+    ActionItem completeAction = () -> {};
+
+    BooleanSupplier isReadySupplier = () -> {
+      return isReady.get();
+    };
+
+    AsyncServletOutputStreamWriter writer =
+        new AsyncServletOutputStreamWriter(writeAction, flushAction, completeAction, isReadySupplier, new Log() {});
+
+    // Initial onWritePossible
+    writer.onWritePossible();
+
+    // First write - isReady is true
+    byte[] data1 = new byte[]{1};
+    writer.writeBytes(data1, 1);
+
+    // Simulate isReady becoming false (Tomcat calls onWritePossible when ready)
+    isReady.set(false);
+    writer.onWritePossible();
+
+    // Second write after isReady returns to true
+    isReady.set(true);
+    byte[] data2 = new byte[]{2};
+    writer.writeBytes(data2, 1);
+
+    assertEquals("Two writes should complete", 2, actions.size());
+    assertEquals("write", actions.get(0));
+    assertEquals("write", actions.get(1));
+  }
+}
\ No newline at end of file