diff --git a/temporalio/lib/temporalio/internal/worker/workflow_instance/outbound_implementation.rb b/temporalio/lib/temporalio/internal/worker/workflow_instance/outbound_implementation.rb
index 624cb4c1..3be8d123 100644
--- a/temporalio/lib/temporalio/internal/worker/workflow_instance/outbound_implementation.rb
+++ b/temporalio/lib/temporalio/internal/worker/workflow_instance/outbound_implementation.rb
@@ -481,15 +481,25 @@ def start_nexus_operation(input)
               @instance.pending_nexus_operation_starts.delete(seq)
             end
 
-            # Handle start failure
-            if resolution.failed
+            # Handle start resolution
+            case resolution.status
+            when :operation_token
+              operation_token = resolution.operation_token
+            when :started_sync
+              operation_token = nil
+            when :failed
+              input.cancellation.remove_cancel_callback(cancel_callback_key)
+              raise @instance.failure_converter.from_failure(
+                resolution.failed, @instance.payload_converter
+              )
+            else
               input.cancellation.remove_cancel_callback(cancel_callback_key)
-              raise @instance.failure_converter.from_failure(resolution.failed, @instance.payload_converter)
+              raise "Unknown Nexus operation start status: #{resolution.status.inspect}"
             end
 
             # Create handle and add to pending operations (result will come via resolve_nexus_operation)
             handle = NexusOperationHandle.new(
-              operation_token: resolution.operation_token,
+              operation_token:,
               instance: @instance,
               cancellation: input.cancellation,
               cancel_callback_key:,
diff --git a/temporalio/test/worker_workflow_nexus_test.rb b/temporalio/test/worker_workflow_nexus_test.rb
index 90e74911..484d4efd 100644
--- a/temporalio/test/worker_workflow_nexus_test.rb
+++ b/temporalio/test/worker_workflow_nexus_test.rb
@@ -85,14 +85,35 @@ class NexusOperationHandleWorkflow < Temporalio::Workflow::Definition
     workflow_query_attr_reader :operation_token
     workflow_query_attr_reader :has_token
 
-    def execute(endpoint, operation, input)
+    workflow_signal
+    def complete
+      @complete = true
+    end
+
+    def execute(endpoint, operation, input, after_start = nil)
       client = Temporalio::Workflow.create_nexus_client(endpoint:, service: 'test-service')
-      handle = client.start_operation(operation, input)
+      cancellation, cancel_proc = Temporalio::Cancellation.new
+      handle = client.start_operation(operation, input, cancellation:)
 
       @operation_token = handle.operation_token
-      @has_token = !handle.operation_token.nil?
+      @has_token = !@operation_token.nil?
+      case after_start
+      when 'cancel'
+        Temporalio::Workflow.wait_condition { @complete }
+        cancel_proc.call
+      when nil
+        nil
+      else
+        raise "Unrecognized after-start action: #{after_start}"
+      end
 
-      handle.result
+      begin
+        handle.result
+      rescue Temporalio::Error::NexusOperationError => e
+        return { 'cancelled' => true } if after_start == 'cancel' && e.cause.is_a?(Temporalio::Error::CanceledError)
+
+        raise
+      end
     end
   end
 
@@ -104,7 +125,8 @@ def test_nexus_operation_handle_async_has_token
         NexusOperationHandleWorkflow,
         endpoint,
         'workflow-operation',
-        { 'action' => 'success' }
+        { 'action' => 'wait-for-cancel' },
+        'cancel'
       ) do |handle|
         # Wait for operation to start
         assert_eventually { assert handle.query(NexusOperationHandleWorkflow.has_token) }
@@ -113,25 +135,24 @@ def test_nexus_operation_handle_async_has_token
         refute_nil token
         assert token.length.positive? # steep:ignore
 
+        handle.signal(NexusOperationHandleWorkflow.complete)
         result = handle.result
-        assert_equal 'success', result['result'] # steep:ignore
+        assert_equal true, result['cancelled'] # steep:ignore
       end
     end
   end
 
-  def test_nexus_operation_handle_sync_has_token
+  def test_nexus_operation_handle_sync_has_no_token
     env.with_kitchen_sink_worker(nexus: true) do |task_queue|
       endpoint = "nexus-endpoint-#{task_queue}"
 
       execute_workflow(NexusOperationHandleWorkflow, endpoint, 'echo', 'success') do |handle|
-        # Even sync operations have tokens when using start_operation
-        assert_eventually { assert handle.query(NexusOperationHandleWorkflow.has_token) }
-
-        token = handle.query(NexusOperationHandleWorkflow.operation_token)
-        refute_nil token
-
         result = handle.result
         assert_equal 'success', result
+
+        token = handle.query(NexusOperationHandleWorkflow.operation_token)
+        assert_nil token
+        assert_equal false, handle.query(NexusOperationHandleWorkflow.has_token)
       end
     end
   end