diff --git a/sql/connect/server/src/main/scala/org/apache/spark/sql/connect/service/SparkConnectExecutePlanHandler.scala b/sql/connect/server/src/main/scala/org/apache/spark/sql/connect/service/SparkConnectExecutePlanHandler.scala
index 1ab5f26f90b13..73a20e448be87 100644
--- a/sql/connect/server/src/main/scala/org/apache/spark/sql/connect/service/SparkConnectExecutePlanHandler.scala
+++ b/sql/connect/server/src/main/scala/org/apache/spark/sql/connect/service/SparkConnectExecutePlanHandler.scala
@@ -31,6 +31,15 @@ class SparkConnectExecutePlanHandler(responseObserver: StreamObserver[proto.Exec
     try {
       executeHolder.eventsManager.postStarted()
       executeHolder.start()
+    } catch {
+      // Errors raised before the execution holder has finished spawning a thread are considered
+      // plan execution failure, and the client should not try reattaching it afterwards.
+      case t: Throwable =>
+        SparkConnectService.executionManager.removeExecuteHolder(executeHolder.key)
+        throw t
+    }
+
+    try {
       val responseSender =
         new ExecuteGrpcResponseSender[proto.ExecutePlanResponse](executeHolder, responseObserver)
       executeHolder.runGrpcResponseSender(responseSender)
diff --git a/sql/connect/server/src/test/scala/org/apache/spark/sql/connect/execution/ReattachableExecuteSuite.scala b/sql/connect/server/src/test/scala/org/apache/spark/sql/connect/execution/ReattachableExecuteSuite.scala
index 25e6cc48a1998..2606284c25bd5 100644
--- a/sql/connect/server/src/test/scala/org/apache/spark/sql/connect/execution/ReattachableExecuteSuite.scala
+++ b/sql/connect/server/src/test/scala/org/apache/spark/sql/connect/execution/ReattachableExecuteSuite.scala
@@ -429,4 +429,27 @@ class ReattachableExecuteSuite extends SparkConnectServerTest {
     val abandonedExecutions = manager.listAbandonedExecutions
     assert(abandonedExecutions.forall(_.operationId != dummyOpId))
   }
+
+  test("SPARK-49492: reattach must not succeed on an inactive execution holder") {
+    withRawBlockingStub { stub =>
+      val operationId = UUID.randomUUID().toString
+
+      // supply an invalid plan so that the execute plan handler raises an error
+      val iter = stub.executePlan(
+        buildExecutePlanRequest(proto.Plan.newBuilder().build(), operationId = operationId))
+
+      // expect that the execution fails before spawning an execute thread
+      val ee = intercept[StatusRuntimeException] {
+        iter.next()
+      }
+      assert(ee.getMessage.contains("INTERNAL"))
+
+      // reattach must fail
+      val reattach = stub.reattachExecute(buildReattachExecuteRequest(operationId, None))
+      val re = intercept[StatusRuntimeException] {
+        reattach.hasNext()
+      }
+      assert(re.getMessage.contains("INVALID_HANDLE.OPERATION_NOT_FOUND"))
+    }
+  }
 }