diff --git a/temporal-sdk/src/test/java/io/temporal/workflow/nexus/SyncOperationTimeoutTest.java b/temporal-sdk/src/test/java/io/temporal/workflow/nexus/SyncOperationTimeoutTest.java
index 21a5a4236..1dd6ac566 100644
--- a/temporal-sdk/src/test/java/io/temporal/workflow/nexus/SyncOperationTimeoutTest.java
+++ b/temporal-sdk/src/test/java/io/temporal/workflow/nexus/SyncOperationTimeoutTest.java
@@ -61,7 +61,7 @@ public static class TestNexus implements TestWorkflows.TestWorkflow1 {
     public String execute(String input) {
       NexusOperationOptions options =
           NexusOperationOptions.newBuilder()
-              .setScheduleToCloseTimeout(Duration.ofSeconds(1))
+              .setScheduleToCloseTimeout(Duration.ofSeconds(5))
               .build();
       NexusServiceOptions serviceOptions =
           NexusServiceOptions.newBuilder().setOperationOptions(options).build();
@@ -74,14 +74,22 @@ public String execute(String input) {
 
   @ServiceImpl(service = TestNexusServices.TestNexusService1.class)
   public class TestNexusServiceImpl {
+    int attempt = 0;
+
     @OperationImpl
     public OperationHandler<String, String> operation() {
       // Implemented inline
       return OperationHandler.sync(
           (ctx, details, name) -> {
-            // Simulate a long running operation
+            // Fail the first attempt with a retry-able exception. This tests
+            // the schedule-to-close timeout applies across attempts.
+            attempt += 1;
+            if (attempt == 1) {
+              throw new RuntimeException("test exception");
+            }
+            // Simulate a long-running operation
             try {
-              Thread.sleep(2000);
+              Thread.sleep(6000);
             } catch (InterruptedException e) {
               throw new RuntimeException(e);
             }
diff --git a/temporal-test-server/src/main/java/io/temporal/internal/testservice/TestWorkflowMutableStateImpl.java b/temporal-test-server/src/main/java/io/temporal/internal/testservice/TestWorkflowMutableStateImpl.java
index 84f5791fa..910b987e2 100644
--- a/temporal-test-server/src/main/java/io/temporal/internal/testservice/TestWorkflowMutableStateImpl.java
+++ b/temporal-test-server/src/main/java/io/temporal/internal/testservice/TestWorkflowMutableStateImpl.java
@@ -62,6 +62,7 @@
 import io.temporal.internal.testservice.StateMachines.ActivityTaskData;
 import io.temporal.internal.testservice.StateMachines.CancelExternalData;
 import io.temporal.internal.testservice.StateMachines.ChildWorkflowData;
+import io.temporal.internal.testservice.StateMachines.NexusOperationData;
 import io.temporal.internal.testservice.StateMachines.SignalExternalData;
 import io.temporal.internal.testservice.StateMachines.State;
 import io.temporal.internal.testservice.StateMachines.TimerData;
@@ -782,14 +783,18 @@ private void processScheduleNexusOperation(
     nexusOperations.put(scheduleEventId, operation);
 
     operation.action(Action.INITIATE, ctx, attr, workflowTaskCompletedId);
+    // Record the current attempt of this request to be used in the timeout handler
+    // of this request to make sure we are timing out the correct request.
+    int attempt = operation.getData().getAttempt();
     ctx.addTimer(
         ProtobufTimeUtils.toJavaDuration(operation.getData().requestTimeout),
-        () ->
-            timeoutNexusRequest(
-                scheduleEventId, "StartNexusOperation", operation.getData().getAttempt()),
+        () -> timeoutNexusRequest(scheduleEventId, "StartNexusOperation", attempt),
         "StartNexusOperation request timeout");
     if (attr.hasScheduleToCloseTimeout()
         && Durations.toMillis(attr.getScheduleToCloseTimeout()) > 0) {
+      // ScheduleToCloseTimeout is the total time from the start of the operation to the end of the
+      // operation
+      // so the attempt is not relevant here.
       ctx.addTimer(
           ProtobufTimeUtils.toJavaDuration(attr.getScheduleToCloseTimeout()),
           () ->
@@ -978,6 +983,7 @@ private void processScheduleActivityTask(
     ActivityTaskScheduledEventAttributes scheduledEvent =
         activityStateMachine.getData().scheduledEvent;
     int attempt = activityStateMachine.getData().getAttempt();
+    // TODO(quinn) If the first attempt fails, it is not clear this timer will work as expected
     ctx.addTimer(
         ProtobufTimeUtils.toJavaDuration(scheduledEvent.getScheduleToCloseTimeout()),
         () ->