diff --git a/clients/src/main/java/org/apache/kafka/clients/producer/internals/TransactionManager.java b/clients/src/main/java/org/apache/kafka/clients/producer/internals/TransactionManager.java
index 64ee1cd79f6a9..52f47dcbcda78 100644
--- a/clients/src/main/java/org/apache/kafka/clients/producer/internals/TransactionManager.java
+++ b/clients/src/main/java/org/apache/kafka/clients/producer/internals/TransactionManager.java
@@ -687,15 +687,27 @@ synchronized void bumpIdempotentEpochAndResetIdIfNeeded() {
             }
             if (currentState != State.INITIALIZING && !hasProducerId()) {
                 transitionTo(State.INITIALIZING);
-                InitProducerIdRequestData requestData = new InitProducerIdRequestData()
-                        .setTransactionalId(null)
-                        .setTransactionTimeoutMs(Integer.MAX_VALUE);
-                InitProducerIdHandler handler = new InitProducerIdHandler(new InitProducerIdRequest.Builder(requestData), false);
-                enqueueRequest(handler);
+                enqueueInitProducerIdRequest();
+            } else if (currentState == State.INITIALIZING && !hasProducerId()
+                    && pendingRequests.isEmpty() && !hasInFlightRequest()) {
+                // The previous InitProducerId request was dequeued but lost before it could
+                // be sent (e.g., due to an authentication error during connection). Re-enqueue
+                // to allow recovery without requiring a producer restart.
+                log.info("Re-enqueuing InitProducerId request after previous attempt was lost");
+                enqueueInitProducerIdRequest();
             }
         }
     }
 
+    private void enqueueInitProducerIdRequest() {
+        InitProducerIdRequestData requestData = new InitProducerIdRequestData()
+                .setTransactionalId(null)
+                .setTransactionTimeoutMs(Integer.MAX_VALUE);
+        InitProducerIdHandler handler = new InitProducerIdHandler(
+                new InitProducerIdRequest.Builder(requestData), false);
+        enqueueRequest(handler);
+    }
+
     /**
      * Returns the next sequence number to be written to the given TopicPartition.
      */
diff --git a/clients/src/test/java/org/apache/kafka/clients/producer/internals/TransactionManagerTest.java b/clients/src/test/java/org/apache/kafka/clients/producer/internals/TransactionManagerTest.java
index a13e44a5e16df..672e759e529ab 100644
--- a/clients/src/test/java/org/apache/kafka/clients/producer/internals/TransactionManagerTest.java
+++ b/clients/src/test/java/org/apache/kafka/clients/producer/internals/TransactionManagerTest.java
@@ -4613,6 +4613,34 @@ private void assertProduceFutureFailed(Future<RecordMetadata> future) throws Int
         }
     }
 
+    @Test
+    public void testIdempotentProducerRecoversFromLostInitProducerIdRequest() {
+        // Simulate the scenario from KAFKA-20237: InitProducerId request is dequeued
+        // but lost due to authentication failure, leaving state stuck at INITIALIZING.
+        // Note: isInitializing() checks isTransactional(), so we verify state via
+        // behavioral assertions (request enqueue/dequeue) rather than state checks.
+        initializeTransactionManager(Optional.empty(), false);
+
+        // First call transitions to INITIALIZING and enqueues request
+        transactionManager.bumpIdempotentEpochAndResetIdIfNeeded();
+
+        // Verify a request was enqueued by dequeuing it (as nextRequest() would in Sender)
+        TransactionManager.TxnRequestHandler handler = transactionManager.nextRequest(false);
+        assertNotNull(handler, "InitProducerIdHandler should have been enqueued");
+
+        // Simulate authentication failure: the request was dequeued but never sent.
+        // authenticationFailed() iterates pendingRequests (now empty) so it does nothing.
+        transactionManager.authenticationFailed(new org.apache.kafka.common.errors.AuthenticationException("SSL handshake failed"));
+
+        // On the next Sender iteration, bumpIdempotentEpochAndResetIdIfNeeded should
+        // detect the lost request and re-enqueue
+        transactionManager.bumpIdempotentEpochAndResetIdIfNeeded();
+
+        // Verify a new request was re-enqueued
+        TransactionManager.TxnRequestHandler retryHandler = transactionManager.nextRequest(false);
+        assertNotNull(retryHandler, "A new InitProducerIdHandler should have been re-enqueued");
+    }
+
     private void runUntil(Supplier<Boolean> condition) {
         ProducerTestUtils.runUntil(sender, condition);
     }