diff --git a/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java b/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java
index 3c8d3d07571..f3f5f4da689 100644
--- a/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java
+++ b/servlet/src/main/java/io/grpc/servlet/AsyncServletOutputStreamWriter.java
@@ -35,7 +35,6 @@
 import java.util.function.BooleanSupplier;
 import java.util.logging.Level;
 import java.util.logging.Logger;
-import javax.annotation.Nullable;
 import javax.servlet.AsyncContext;
 import javax.servlet.ServletOutputStream;
 
@@ -78,8 +77,6 @@ final class AsyncServletOutputStreamWriter {
   private final Queue<ActionItem> writeChain = new ConcurrentLinkedQueue<>();
   // for a theoretical race condition that onWritePossible() is called immediately after isReady()
   // returns false and before writeState.compareAndSet()
-  @Nullable
-  private volatile Thread parkingThread;
 
   AsyncServletOutputStreamWriter(
       AsyncContext asyncContext,
@@ -202,11 +199,9 @@ private void assureReadyAndDrainedTurnsFalse() {
     // readyAndDrained should have been set to false already.
     // Just in case due to a race condition readyAndDrained is still true at this moment and is
     // being set to false by runOrBuffer() concurrently.
-    parkingThread = Thread.currentThread();
     while (writeState.get().readyAndDrained) {
       LockSupport.parkNanos(TimeUnit.MINUTES.toNanos(1)); // should return immediately
     }
-    parkingThread = null;
   }
 
   /**
@@ -217,7 +212,21 @@ private void assureReadyAndDrainedTurnsFalse() {
    */
   private void runOrBuffer(ActionItem actionItem) throws IOException {
     WriteState curState = writeState.get();
-    if (curState.readyAndDrained) { // write to the outputStream directly
+
+    // --- NEW: Tomcat Spontaneous State Change Mitigation ---
+    // If our cache says true, but the container is secretly not ready,
+    // intercept the stale state and sync it before proceeding.
+    if (curState.readyAndDrained && !isReady.getAsBoolean()) {
+      boolean successful = writeState.compareAndSet(curState, curState.withReadyAndDrained(false));
+      checkState(successful, "Bug: curState is unexpectedly changed by another thread");
+      // Update local state so it gracefully bypasses the 
+      // direct write and falls into the buffer block
+      curState = writeState.get(); 
+    }
+    // -------------------------------------------------------
+
+    // The rest is the standard, original gRPC code!
+    if (curState.readyAndDrained) {
       actionItem.run();
       if (actionItem == completeAction) {
         return;
@@ -225,22 +234,21 @@ private void runOrBuffer(ActionItem actionItem) throws IOException {
       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);
-      if (!writeState.compareAndSet(curState, curState.withReadyAndDrained(false))) {
-        checkState(
-            writeState.get().readyAndDrained,
-            "Bug: onWritePossible() should have changed readyAndDrained to true, but not");
-        ActionItem lastItem = writeChain.poll();
-        if (lastItem != null) {
-          checkState(lastItem == actionItem, "Bug: lastItem != actionItem");
-          runOrBuffer(lastItem);
-        }
-      } // state has not changed since
+      return;
+    }
+
+    writeChain.offer(actionItem);
+    if (!writeState.compareAndSet(curState, curState.withReadyAndDrained(false))) {
+      checkState(
+          writeState.get().readyAndDrained,
+          "Bug: onWritePossible() should have changed readyAndDrained to true, but not");
+      ActionItem lastItem = writeChain.poll();
+      if (lastItem != null) {
+        checkState(lastItem == actionItem, "Bug: lastItem != actionItem");
+        runOrBuffer(lastItem);
+      }
     }
   }