diff --git a/cli.py b/cli.py
index 2783ca31bf2..bd8696178d5 100644
--- a/cli.py
+++ b/cli.py
@@ -10221,6 +10221,7 @@ class HermesCLI:
             self._voice_processing = True
 
         submitted = False
+        transcription_failed = False
         wav_path = None
         try:
             if self._voice_recorder is None:
@@ -10269,18 +10270,24 @@ class HermesCLI:
             else:
                 error = result.get("error", "Unknown error")
                 _cprint(f"\n{_DIM}Transcription failed: {error}{_RST}")
+                transcription_failed = True
 
         except Exception as e:
             _cprint(f"\n{_DIM}Voice processing error: {e}{_RST}")
+            transcription_failed = wav_path is not None
         finally:
             with self._voice_lock:
                 self._voice_processing = False
             if hasattr(self, '_app') and self._app:
                 self._app.invalidate()
-            # Clean up temp file
+            # Clean up temp file unless transcription failed. On failure, keep
+            # the source recording so long dictation is not lost.
             try:
                 if wav_path and os.path.isfile(wav_path):
-                    os.unlink(wav_path)
+                    if transcription_failed:
+                        _cprint(f"{_DIM}Recording preserved at: {wav_path}{_RST}")
+                    else:
+                        os.unlink(wav_path)
             except Exception:
                 pass
 
diff --git a/tests/tools/test_voice_cli_integration.py b/tests/tools/test_voice_cli_integration.py
index a6cf5e36627..babdb4e7383 100644
--- a/tests/tools/test_voice_cli_integration.py
+++ b/tests/tools/test_voice_cli_integration.py
@@ -1214,6 +1214,11 @@ class TestVoiceStopAndTranscribeReal:
         cli = _make_voice_cli(_voice_recording=True, _voice_recorder=recorder)
         cli._voice_stop_and_transcribe()
         assert cli._pending_input.empty()
+        _unl.assert_not_called()
+        assert any(
+            "Recording preserved at: /tmp/test.wav" in str(call)
+            for call in _cp.call_args_list
+        )
 
     @patch("cli._cprint")
     @patch("cli.os.unlink")
@@ -1227,6 +1232,11 @@ class TestVoiceStopAndTranscribeReal:
         recorder.stop.return_value = "/tmp/test.wav"
         cli = _make_voice_cli(_voice_recording=True, _voice_recorder=recorder)
         cli._voice_stop_and_transcribe()  # Should not raise
+        _unl.assert_not_called()
+        assert any(
+            "Recording preserved at: /tmp/test.wav" in str(call)
+            for call in _cp.call_args_list
+        )
 
     @patch("cli._cprint")
     @patch("tools.voice_mode.play_beep")
diff --git a/tests/tools/test_voice_mode.py b/tests/tools/test_voice_mode.py
index 1d35c48625f..4c7ba74bd6e 100644
--- a/tests/tools/test_voice_mode.py
+++ b/tests/tools/test_voice_mode.py
@@ -586,6 +586,73 @@ class TestTranscribeRecording:
         assert result["transcript"] == "Thank you for helping me with this code."
         assert "filtered" not in result
 
+    def test_oversized_wav_is_chunked_and_stitched(self, tmp_path, monkeypatch):
+        wav_path = tmp_path / "long.wav"
+        n_frames = 50000
+        audio = struct.pack(f"<{n_frames}h", *([1000] * n_frames))
+        with wave.open(str(wav_path), "wb") as wf:
+            wf.setnchannels(1)
+            wf.setsampwidth(2)
+            wf.setframerate(16000)
+            wf.writeframes(audio)
+
+        temp_dir = tmp_path / "chunks"
+        temp_dir.mkdir()
+        monkeypatch.setattr("tools.voice_mode._TEMP_DIR", str(temp_dir))
+        monkeypatch.setattr("tools.transcription_tools.MAX_FILE_SIZE", 70 * 1024)
+
+        seen_paths = []
+
+        def fake_transcribe(path, model=None):
+            seen_paths.append(path)
+            assert model == "base"
+            assert path != str(wav_path)
+            assert os.path.getsize(path) <= 70 * 1024
+            return {
+                "success": True,
+                "transcript": f"part {len(seen_paths)}",
+                "provider": "local",
+            }
+
+        with patch("tools.transcription_tools.transcribe_audio", side_effect=fake_transcribe):
+            from tools.voice_mode import transcribe_recording
+            result = transcribe_recording(str(wav_path), model="base")
+
+        assert result["success"] is True
+        assert result["transcript"] == " ".join(
+            f"part {i}" for i in range(1, len(seen_paths) + 1)
+        )
+        assert result["chunks"] == len(seen_paths)
+        assert len(seen_paths) > 1
+        assert all(not os.path.exists(path) for path in seen_paths)
+
+    def test_oversized_wav_reports_failing_chunk(self, tmp_path, monkeypatch):
+        wav_path = tmp_path / "long.wav"
+        n_frames = 50000
+        audio = struct.pack(f"<{n_frames}h", *([1000] * n_frames))
+        with wave.open(str(wav_path), "wb") as wf:
+            wf.setnchannels(1)
+            wf.setsampwidth(2)
+            wf.setframerate(16000)
+            wf.writeframes(audio)
+
+        temp_dir = tmp_path / "chunks"
+        temp_dir.mkdir()
+        monkeypatch.setattr("tools.voice_mode._TEMP_DIR", str(temp_dir))
+        monkeypatch.setattr("tools.transcription_tools.MAX_FILE_SIZE", 70 * 1024)
+
+        def fake_transcribe(path, model=None):
+            return {"success": False, "transcript": "", "error": "provider rejected audio"}
+
+        with patch("tools.transcription_tools.transcribe_audio", side_effect=fake_transcribe):
+            from tools.voice_mode import transcribe_recording
+            result = transcribe_recording(str(wav_path), model="base")
+
+        assert result["success"] is False
+        assert result["error"].startswith("Chunk 1/")
+        assert "provider rejected audio" in result["error"]
+        assert list(temp_dir.iterdir()) == []
+
 
 class TestWhisperHallucinationFilter:
     def test_known_hallucinations(self):
diff --git a/tools/voice_mode.py b/tools/voice_mode.py
index cc691afad7d..d28775ac63a 100644
--- a/tools/voice_mode.py
+++ b/tools/voice_mode.py
@@ -800,9 +800,12 @@ def transcribe_recording(wav_path: str, model: Optional[str] = None) -> Dict[str
     Returns:
         Dict with ``success``, ``transcript``, and optionally ``error``.
     """
-    from tools.transcription_tools import transcribe_audio
+    from tools.transcription_tools import MAX_FILE_SIZE, transcribe_audio
 
-    result = transcribe_audio(wav_path, model=model)
+    if _should_chunk_for_transcription(wav_path, MAX_FILE_SIZE):
+        result = _transcribe_wav_in_chunks(wav_path, model=model, max_file_size=MAX_FILE_SIZE)
+    else:
+        result = transcribe_audio(wav_path, model=model)
 
     # Filter out Whisper hallucinations (common on silent/near-silent audio)
     if result.get("success") and is_whisper_hallucination(result.get("transcript", "")):
@@ -812,6 +815,114 @@ def transcribe_recording(wav_path: str, model: Optional[str] = None) -> Dict[str
     return result
 
 
+def _should_chunk_for_transcription(file_path: str, max_file_size: int) -> bool:
+    """Return whether a CLI WAV recording needs to be split before STT."""
+    if not file_path.lower().endswith(".wav"):
+        return False
+    try:
+        return os.path.getsize(file_path) > max_file_size
+    except OSError:
+        return False
+
+
+def _transcribe_wav_in_chunks(
+    wav_path: str,
+    *,
+    model: Optional[str],
+    max_file_size: int,
+) -> Dict[str, Any]:
+    """Split an oversized WAV into provider-sized chunks and join transcripts."""
+    from tools.transcription_tools import transcribe_audio
+
+    chunk_paths: List[str] = []
+    transcripts: List[str] = []
+
+    try:
+        chunk_paths = _split_wav_for_transcription(wav_path, max_file_size=max_file_size)
+        if not chunk_paths:
+            return {"success": False, "transcript": "", "error": "No audio chunks were created"}
+
+        logger.info("Transcribing oversized WAV in %d chunks: %s", len(chunk_paths), wav_path)
+        for index, chunk_path in enumerate(chunk_paths, start=1):
+            result = transcribe_audio(chunk_path, model=model)
+            if not result.get("success"):
+                error = result.get("error", "Unknown transcription error")
+                return {
+                    "success": False,
+                    "transcript": "",
+                    "error": f"Chunk {index}/{len(chunk_paths)} failed: {error}",
+                }
+
+            transcript = result.get("transcript", "").strip()
+            if transcript and not is_whisper_hallucination(transcript):
+                transcripts.append(transcript)
+
+        return {
+            "success": True,
+            "transcript": " ".join(transcripts).strip(),
+            "provider": result.get("provider"),
+            "chunks": len(chunk_paths),
+        }
+    except Exception as e:
+        logger.error("Chunked transcription failed for %s: %s", wav_path, e, exc_info=True)
+        return {"success": False, "transcript": "", "error": f"Chunked transcription failed: {e}"}
+    finally:
+        for chunk_path in chunk_paths:
+            try:
+                if os.path.isfile(chunk_path):
+                    os.unlink(chunk_path)
+            except OSError:
+                pass
+
+
+def _split_wav_for_transcription(wav_path: str, *, max_file_size: int) -> List[str]:
+    """Write WAV chunks small enough to pass the shared STT file-size gate."""
+    os.makedirs(_TEMP_DIR, exist_ok=True)
+    chunk_paths: List[str] = []
+    header_reserve = 64 * 1024
+
+    with wave.open(wav_path, "rb") as source:
+        params = source.getparams()
+        block_align = max(1, params.nchannels * params.sampwidth)
+        max_data_bytes = max_file_size - header_reserve
+        if max_data_bytes < block_align:
+            raise ValueError("STT max_file_size is too small for WAV chunking")
+
+        frames_per_chunk = max(1, max_data_bytes // block_align)
+        index = 0
+        while True:
+            frames = source.readframes(frames_per_chunk)
+            if not frames:
+                break
+
+            index += 1
+            temp = tempfile.NamedTemporaryFile(
+                prefix=f"{os.path.splitext(os.path.basename(wav_path))[0]}_chunk{index:03d}_",
+                suffix=".wav",
+                dir=_TEMP_DIR,
+                delete=False,
+            )
+            chunk_path = temp.name
+            temp.close()
+
+            try:
+                with wave.open(chunk_path, "wb") as chunk:
+                    chunk.setnchannels(params.nchannels)
+                    chunk.setsampwidth(params.sampwidth)
+                    chunk.setframerate(params.framerate)
+                    chunk.setcomptype(params.comptype, params.compname)
+                    chunk.writeframes(frames)
+                chunk_paths.append(chunk_path)
+            except Exception:
+                try:
+                    os.unlink(chunk_path)
+                except OSError:
+                    pass
+                raise
+
+    return chunk_paths
+
+
 # ============================================================================
 # Audio playback (interruptable)
 # ============================================================================