diff --git a/temporalio/lib/temporalio/internal/client/implementation.rb b/temporalio/lib/temporalio/internal/client/implementation.rb
index c181e54f..395769be 100644
--- a/temporalio/lib/temporalio/internal/client/implementation.rb
+++ b/temporalio/lib/temporalio/internal/client/implementation.rb
@@ -492,6 +492,10 @@ def start_workflow_update(input)
           # the user cannot specify sooner than ACCEPTED)
           # @type var resp: untyped
           resp = nil
+          expected_stage = ProtoUtils.enum_to_int(Api::Enums::V1::UpdateWorkflowExecutionLifecycleStage,
+                                                  req.wait_policy.lifecycle_stage)
+          accepted_stage = ProtoUtils.enum_to_int(Api::Enums::V1::UpdateWorkflowExecutionLifecycleStage,
+                                                  Temporalio::Client::WorkflowUpdateWaitStage::ACCEPTED)
           loop do
             resp = @client.workflow_service.update_workflow_execution(
               req,
@@ -500,10 +504,8 @@ def start_workflow_update(input)
 
             # We're only done if the response stage is after the requested stage
             # or the response stage is accepted
-            if resp.stage >= req.wait_policy.lifecycle_stage ||
-               resp.stage >= Temporalio::Client::WorkflowUpdateWaitStage::ACCEPTED
-              break
-            end
+            actual_stage = ProtoUtils.enum_to_int(Api::Enums::V1::UpdateWorkflowExecutionLifecycleStage, resp.stage)
+            break if actual_stage >= expected_stage || actual_stage >= accepted_stage
           rescue Error::RPCError => e
             # Deadline exceeded or cancel is a special error type
             if e.code == Error::RPCError::Code::DEADLINE_EXCEEDED || e.code == Error::RPCError::Code::CANCELED
diff --git a/temporalio/test/worker_workflow_handler_test.rb b/temporalio/test/worker_workflow_handler_test.rb
index 595aaee3..4d941a51 100644
--- a/temporalio/test/worker_workflow_handler_test.rb
+++ b/temporalio/test/worker_workflow_handler_test.rb
@@ -619,6 +619,56 @@ def test_update_info
     end)
   end
 
+  class RetryStartUpdateWorkflow < Temporalio::Workflow::Definition
+    def execute
+      Temporalio::Workflow.wait_condition { false }
+    end
+
+    workflow_update
+    def some_update
+      'done'
+    end
+  end
+
+  def test_retry_start_update
+    # This test confirms that the UpdateWorkflowExecution call occurs multiple times if it hasn't reached accepted. We
+    # check this via metrics.
+    buffer = Temporalio::Runtime::MetricBuffer.new(10_000)
+    Temporalio::Testing::WorkflowEnvironment.start_local(
+      runtime: Temporalio::Runtime.new(
+        telemetry: Temporalio::Runtime::TelemetryOptions.new(metrics: Temporalio::Runtime::MetricsOptions.new(buffer:))
+      ),
+      logger: Logger.new($stdout),
+      # Reduce poll interval so it tries again sooner
+      dev_server_extra_args: ['--dynamic-config-value', 'history.longPollExpirationInterval="3s"']
+    ) do |local_env|
+      # Start workflow, then issue update without a running worker
+      task_queue = "tq-#{SecureRandom.uuid}"
+      handle = local_env.client.start_workflow(RetryStartUpdateWorkflow, id: "wf-#{SecureRandom.uuid}", task_queue:)
+
+      # Wait for update in background
+      queue = Queue.new
+      run_in_background { queue << handle.execute_update(RetryStartUpdateWorkflow.some_update) }
+
+      # Wait for there to be at least 2 update requests
+      update_requests = 0
+      assert_eventually do
+        buffer.retrieve_updates.each do |update|
+          if update.metric.name == 'temporal_long_request' &&
+             update.attributes['operation'] == 'UpdateWorkflowExecution'
+            update_requests += update.value # steep:ignore
+          end
+        end
+        assert update_requests >= 2
+      end
+
+      # Now run the worker that will let the update be processed
+      Temporalio::Worker.new(client: local_env.client, task_queue:, workflows: [RetryStartUpdateWorkflow]).run do
+        assert_equal 'done', queue.pop(timeout: 5)
+      end
+    end
+  end
+
   class UpdateWithStartWorkflow < Temporalio::Workflow::Definition
     workflow_query_attr_reader :counter