diff --git a/python/tests/test_transcribe.py b/python/tests/test_transcribe.py
index b0af248..3d035b5 100644
--- a/python/tests/test_transcribe.py
+++ b/python/tests/test_transcribe.py
@@ -67,3 +67,57 @@ def test_on_segment_callback():
     # Verify the parameter exists by checking the signature
     sig = inspect.signature(service.transcribe)
     assert "on_segment" in sig.parameters
+
+
+def test_progress_every_segment(monkeypatch):
+    """Verify a progress message is sent for every segment, not just every 5th."""
+    from unittest.mock import MagicMock, patch
+    from voice_to_notes.services.transcribe import TranscribeService
+
+    # Mock WhisperModel
+    mock_model = MagicMock()
+
+    # Create mock segments (8 of them to test > 5)
+    mock_segments = []
+    for i in range(8):
+        seg = MagicMock()
+        seg.start = i * 1.0
+        seg.end = (i + 1) * 1.0
+        seg.text = f"Segment {i}"
+        seg.words = []
+        mock_segments.append(seg)
+
+    # Mock info object
+    mock_info = MagicMock()
+    mock_info.language = "en"
+    mock_info.language_probability = 0.99
+    mock_info.duration = 8.0
+
+    mock_model.transcribe.return_value = (iter(mock_segments), mock_info)
+
+    # Track write_message calls
+    written_messages = []
+
+    def mock_write(msg):
+        written_messages.append(msg)
+
+    service = TranscribeService()
+    service._model = mock_model
+    service._current_model_name = "base"
+    service._current_device = "cpu"
+    service._current_compute_type = "int8"
+
+    with patch("voice_to_notes.services.transcribe.write_message", mock_write):
+        service.transcribe("req-1", "/fake/audio.wav")
+
+    # Filter for "transcribing" stage progress messages
+    transcribing_msgs = [
+        m for m in written_messages
+        if m.type == "progress" and m.payload.get("stage") == "transcribing"
+    ]
+
+    # Should have one per segment (8) + the initial "Starting transcription..." message
+    # The initial "Starting transcription..." is also stage "transcribing" — so 8 + 1 = 9
+    assert len(transcribing_msgs) >= 8, (
+        f"Expected at least 8 transcribing progress messages (one per segment), got {len(transcribing_msgs)}"
+    )
diff --git a/python/voice_to_notes/services/transcribe.py b/python/voice_to_notes/services/transcribe.py
index 7a0b67c..1ed1904 100644
--- a/python/voice_to_notes/services/transcribe.py
+++ b/python/voice_to_notes/services/transcribe.py
@@ -150,16 +150,14 @@ class TranscribeService:
             if on_segment:
                 on_segment(result.segments[-1], segment_count - 1)
 
-            # Send progress every few segments
-            if segment_count % 5 == 0:
-                write_message(
-                    progress_message(
-                        request_id,
-                        progress_pct,
-                        "transcribing",
-                        f"Processed {segment_count} segments...",
-                    )
+            write_message(
+                progress_message(
+                    request_id,
+                    progress_pct,
+                    "transcribing",
+                    f"Transcribing segment {segment_count} ({progress_pct}% of audio)...",
                 )
+            )
 
         elapsed = time.time() - start_time
         print(