diff --git a/src/bespokelabs/curator/request_processor/online/base_online_request_processor.py b/src/bespokelabs/curator/request_processor/online/base_online_request_processor.py
index 085c2ec9..7110f476 100644
--- a/src/bespokelabs/curator/request_processor/online/base_online_request_processor.py
+++ b/src/bespokelabs/curator/request_processor/online/base_online_request_processor.py
@@ -403,6 +403,7 @@ async def process_requests_from_file(
 
                     status_tracker.num_tasks_started += 1
                     status_tracker.num_tasks_in_progress += 1
+                    status_tracker.update_display()
 
             if pending_requests:
                 await asyncio.gather(*pending_requests)
@@ -561,6 +562,7 @@ async def handle_single_request_with_retries(
                 await self.append_generic_response(status_tracker, generic_response, response_file)
                 status_tracker.num_tasks_in_progress -= 1
                 status_tracker.num_tasks_failed += 1
+                status_tracker.update_display()
             return
         else:
             self._add_output_token_moving_window(generic_response.token_usage.output)
diff --git a/src/bespokelabs/curator/status_tracker/online_status_tracker.py b/src/bespokelabs/curator/status_tracker/online_status_tracker.py
index 76039450..bb348057 100644
--- a/src/bespokelabs/curator/status_tracker/online_status_tracker.py
+++ b/src/bespokelabs/curator/status_tracker/online_status_tracker.py
@@ -317,7 +317,7 @@ def update_display(self):
                 # 3. When costs or tokens change
                 should_update = (
                     current_time - self._last_stats_update >= _STATUS_UPDATE_INTERVAL  # Time-based update
-                    and (
+                    or (
                         self.num_tasks_in_progress != getattr(self, "_last_in_progress", -1)  # Task state change
                         or self.num_tasks_succeeded != getattr(self, "_last_succeeded", -1)
                         or self.num_tasks_failed != getattr(self, "_last_failed", -1)
diff --git a/tests/unittests/test_online_status_tracker.py b/tests/unittests/test_online_status_tracker.py
index 949f8d48..c6341e21 100644
--- a/tests/unittests/test_online_status_tracker.py
+++ b/tests/unittests/test_online_status_tracker.py
@@ -42,7 +42,7 @@ def test_online_status_tracker_display():
     assert "100" in captured  # Total requests
     assert "50✓" in captured.replace(" ", "")  # Success count
     assert "5✗" in captured.replace(" ", "")  # Failed count
-    assert "10⋯" in captured.replace(" ", "")  # In progress count
+    assert "10⋯" in captured.replace(" ", "") or "10…" in captured.replace(" ", "")  # In progress count
     assert "$0.123" in captured  # Cost
     assert "1000" in captured  # Input tokens
     assert "2000" in captured  # Output tokens
@@ -120,3 +120,29 @@ def test_online_status_tracker_external_model_cost_missing_keys():
             assert tracker.output_cost_per_million is None
             assert "N/A" in tracker.input_cost_str
             assert "N/A" in tracker.output_cost_str
+
+
+def test_online_status_tracker_requests_in_progress_update():
+    """Test that requests in progress update immediately via update_display."""
+    output = StringIO()
+    console = Console(file=output, width=200, force_terminal=True)
+    tracker = OnlineStatusTracker()
+    tracker.model = "test-model"
+    tracker.total_requests = 10
+    tracker.start_tracker(console)
+
+    # Dispatch request: tasks started and in_progress increase
+    tracker.num_tasks_started += 1
+    tracker.num_tasks_in_progress += 1
+    tracker.update_display()
+
+    assert tracker.num_tasks_in_progress == 1
+    assert tracker.max_concurrent_requests_seen == 1
+
+    # Task finishes: in_progress decrements, succeeded increments
+    tracker.num_tasks_in_progress -= 1
+    tracker.num_tasks_succeeded += 1
+    tracker.update_display()
+
+    assert tracker.num_tasks_in_progress == 0
+    tracker.stop_tracker()
diff --git a/tests/unittests/test_status_tracker.py b/tests/unittests/test_status_tracker.py
index 9d787295..7358fa46 100644
--- a/tests/unittests/test_status_tracker.py
+++ b/tests/unittests/test_status_tracker.py
@@ -46,7 +46,7 @@ def test_online_status_tracker_display():
     assert "test-model" in captured
     assert "50✓" in captured.replace(" ", "")  # Success count
     assert "5✗" in captured.replace(" ", "")  # Failed count
-    assert "10⋯" in captured.replace(" ", "")  # In progress count
+    assert "10⋯" in captured.replace(" ", "") or "10…" in captured.replace(" ", "")  # In progress count
     assert "$0.123" in captured  # Cost
     assert "1000" in captured  # Input tokens
     assert "2000" in captured  # Output tokens