Keep long recordings: spool, retry, chunked upload, progress ring

A long clip used to die on a fixed 30 s timeout and the audio went with it.
Now every conditioned clip is written to spool/ before upload and only
removed once its text is on the clipboard; failures keep it, and a tray item
retries spooled clips (copied together, never dispatched). Requests the API
rejects outright (4xx other than 408/429) are not kept.

Timeouts scale with the audio (30 s + 30 s/min, capped at 5 min). Clips over
5 min are cut inside pauses into ~4 min chunks uploaded three at a time and
stitched in order; failed chunks are spooled individually and the partial
transcript is copied with a gap marker. The tray disc fills clockwise as
chunks return.

mic_check.py passes the new timeout tuple.

Co-Authored-By: Claude Fable 5.1 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_016rLFNPygDpRkRwPQakdmYh

blurt.py

@@ -11,6 +11,7 @@ import sys
 import tempfile
 import threading
 import time
+from concurrent.futures import ThreadPoolExecutor
 from dataclasses import dataclass
 from logging.handlers import RotatingFileHandler
 from math import gcd
@@ -99,7 +100,18 @@ RAW_ALSA_DEVICE = re.compile(r"\(hw:\d+,\d+\)")
 SOUND_SERVER_DEVICES = ("pipewire", "pulse", "default")
 APP_NAME = "Blurt"
 APP_DIR = Path(__file__).resolve().parent
+SPOOL_DIR = APP_DIR / "spool"  # clips wait here until their transcript is delivered
 AGENT_PREFIX = "to my agent"
+TIMEOUT_CONNECT_SECONDS = 10.0  # reaching the API is fast or not happening
+TIMEOUT_BASE_SECONDS = 30.0  # enough for a short clip, upload included
+TIMEOUT_PER_AUDIO_MINUTE = 30.0  # LLM-based models take minutes per minute of audio
+TIMEOUT_MAX_SECONDS = 300.0  # past this the request is hung, not working
+CHUNK_TARGET_SECONDS = 240  # where we would like each cut to land
+CHUNK_MAX_SECONDS = 300  # OpenAI refuses uploads past 25 MB, and LLM models crawl
+CHUNK_SEARCH_SECONDS = 30  # how far either side of the target a pause may be
+CHUNK_MIN_LAST_SECONDS = 60  # a tail shorter than this is not worth its own request
+CHUNK_SMOOTH_FRAMES = 15  # 300 ms: cut inside a real pause, not between two words
+CHUNK_WORKERS = 3  # parallel uploads; the clip is recorded, only latency is left
 PID_FILE = Path(tempfile.gettempdir()) / "blurt.pid"
 LOG_FILE = Path(tempfile.gettempdir()) / "blurt.log"
 KEYRING_CREDENTIALS = [
@@ -413,6 +425,183 @@ def condition_audio(samples: np.ndarray) -> np.ndarray:
     return np.clip(amplified, -1.0, 1.0)
 
 
+def transcription_timeout(seconds_of_audio: float) -> tuple[float, float]:
+    """Connect and read timeouts for one upload. A fixed read timeout throws away
+    exactly the long recordings that took the most effort to make."""
+    read = TIMEOUT_BASE_SECONDS + TIMEOUT_PER_AUDIO_MINUTE * (seconds_of_audio / 60.0)
+    return TIMEOUT_CONNECT_SECONDS, min(read, TIMEOUT_MAX_SECONDS)
+
+
+def split_at_silence(samples: np.ndarray) -> list[tuple[int, int]]:
+    """Sample ranges to upload separately, in order and covering the whole clip.
+
+    Cutting is only worth its complexity because a long clip is slow and, past
+    25 MB, refused outright — so cut as rarely as the limit allows, and put each
+    cut in the middle of a pause where losing a few samples costs no word."""
+    total = len(samples)
+    if total <= CHUNK_MAX_SECONDS * SAMPLE_RATE:
+        return [(0, total)]
+
+    frame = SAMPLE_RATE // 50
+    # frame_levels reads dBFS off a float clip in [-1, 1]; the audio we cut is
+    # int16, so scale it or every level logged here is 90 dB too loud.
+    scaled = samples.astype(np.float32) / 32768.0 if samples.dtype == np.int16 else samples
+    levels = frame_levels(scaled)
+    smoothed = np.convolve(
+        levels, np.ones(CHUNK_SMOOTH_FRAMES) / CHUNK_SMOOTH_FRAMES, mode="same"
+    )
+
+    ranges: list[tuple[int, int]] = []
+    start = 0
+    while total - start > CHUNK_MAX_SECONDS * SAMPLE_RATE:
+        # Never exceed the upload limit, and never leave a tail too short to be
+        # worth a request of its own.
+        latest = min(
+            start + int((CHUNK_TARGET_SECONDS + CHUNK_SEARCH_SECONDS) * SAMPLE_RATE),
+            start + CHUNK_MAX_SECONDS * SAMPLE_RATE,
+            total - CHUNK_MIN_LAST_SECONDS * SAMPLE_RATE,
+        )
+        earliest = min(
+            start + int((CHUNK_TARGET_SECONDS - CHUNK_SEARCH_SECONDS) * SAMPLE_RATE),
+            latest,
+        )
+        first_frame = max(earliest // frame, 0)
+        last_frame = min(latest // frame, len(smoothed) - 1)
+        if last_frame <= first_frame:
+            cut, level = latest, float(smoothed[min(first_frame, len(smoothed) - 1)])
+        else:
+            window = smoothed[first_frame : last_frame + 1]
+            quietest = first_frame + int(np.argmin(window))
+            # Frames within 3 dB of the quietest are all the same pause; its
+            # centre is the furthest we can get from either neighbouring word.
+            floor = smoothed[quietest] + 3.0
+            left = right = quietest
+            while left > first_frame and smoothed[left - 1] <= floor:
+                left -= 1
+            while right < last_frame and smoothed[right + 1] <= floor:
+                right += 1
+            level = float(smoothed[quietest])
+            cut = min((left + right) // 2 * frame + frame // 2, latest)
+        cut = max(cut, start + 1)
+        logging.info(
+            "Chunk %d cut at %.1fs: quietest point in the window is %.1f dBFS, "
+            "%.1fs of clip left",
+            len(ranges) + 1,
+            cut / SAMPLE_RATE,
+            level,
+            (total - cut) / SAMPLE_RATE,
+        )
+        ranges.append((start, cut))
+        start = cut
+    ranges.append((start, total))
+    return ranges
+
+
+def _spool_path(name: str) -> Path:
+    """A free path for `name`. Two clips landing in the same millisecond is
+    unlikely, but overwriting one of them would lose it for good."""
+    path = SPOOL_DIR / f"{name}.wav"
+    counter = 1
+    while path.exists():
+        path = SPOOL_DIR / f"{name}-{counter}.wav"
+        counter += 1
+    return path
+
+
+def spool_stem() -> str:
+    """Timestamp down to the millisecond, zero-padded so names still sort oldest
+    first."""
+    now = time.time()
+    return f"{time.strftime('%Y%m%d-%H%M%S', time.localtime(now))}-{int(now * 1000) % 1000:03d}"
+
+
+def _write_spool(samples: np.ndarray, name: str) -> Path | None:
+    """Write one clip into the spool, or None if the spool is unwritable.
+
+    The WAV lands under a `.tmp` name and is renamed into place, so a retry
+    globbing the folder mid-write never picks up half a file."""
+    try:
+        SPOOL_DIR.mkdir(parents=True, exist_ok=True)
+        path = _spool_path(name)
+        partial = path.with_name(f"{path.name}.tmp")
+        wavfile.write(partial, SAMPLE_RATE, samples)
+        os.replace(partial, path)
+        return path
+    except Exception:
+        logging.exception("Could not write %s to the spool %s", name, SPOOL_DIR)
+        return None
+
+
+def spool_capture(samples: np.ndarray) -> Path | None:
+    """Park the clip on disk before uploading it, so a failed request costs a
+    retry instead of the words. Returns None if the spool is unwritable —
+    disk trouble must not stop us from transcribing what is already in memory."""
+    path = _write_spool(samples, spool_stem())
+    if path is None:
+        logging.error("Transcribing from memory without a safety net")
+        return None
+    logging.info("Spooled clip to %s: %d samples", path, len(samples))
+    return path
+
+
+def spool_chunk(samples: np.ndarray, stem: str, index: int) -> Path | None:
+    """Park one failed chunk under its own name, so the retry re-uploads only the
+    audio that is actually missing instead of the whole clip."""
+    path = _write_spool(samples, f"{stem}-part{index:02d}")
+    if path is None:
+        logging.error("Failed chunk %d is not in the spool; its audio is gone", index)
+        return None
+    logging.info("Spooled failed chunk %d to %s: %d samples", index, path, len(samples))
+    return path
+
+
+def load_spooled_capture(path: Path) -> np.ndarray | None:
+    """Read back a spooled clip, refusing anything we did not write ourselves:
+    a stray WAV in the folder would otherwise be uploaded at the wrong rate."""
+    try:
+        rate, samples = wavfile.read(path)
+    except Exception:
+        logging.exception("Could not read spooled clip %s; leaving it in place", path)
+        return None
+    if rate != SAMPLE_RATE or samples.dtype != np.int16 or samples.ndim != 1:
+        logging.warning(
+            "Skipping spooled clip %s: expected int16 mono at %d Hz, got %s %s at %d Hz",
+            path,
+            SAMPLE_RATE,
+            samples.dtype,
+            "mono" if samples.ndim == 1 else f"{samples.ndim}-D",
+            rate,
+        )
+        return None
+    return samples
+
+
+class TranscriptionError(Exception):
+    """The API answered but gave us no usable text, so the clip stays spooled."""
+
+
+def error_text(error: BaseException) -> str:
+    return f"{type(error).__name__}: {error}"
+
+
+def rejected_status(error: BaseException) -> int | None:
+    """The HTTP status if the API refused the request itself, else None.
+
+    A 4xx that is not 408 or 429 says the upload was wrong, not unlucky: the
+    same audio can only be rejected again, so keeping it would leave a clip in
+    the spool that no retry can ever clear."""
+    if not isinstance(error, requests.HTTPError):
+        return None
+    status = getattr(getattr(error, "response", None), "status_code", None)
+    if isinstance(status, int) and 400 <= status < 500 and status not in (408, 429):
+        return status
+    return None
+
+
+def response_snippet(error: BaseException) -> str:
+    return str(getattr(getattr(error, "response", None), "text", ""))[:200]
+
+
 def get_model_label(model: str) -> str:
     for model_id, label, _ in TRANSCRIPTION_MODELS:
         if model_id == model:
@@ -617,6 +806,9 @@ class BlurtApp:
         self.capture_rate = SAMPLE_RATE
         self.capture_channels = CHANNELS
         self.lock = threading.Lock()
+        # Redraws come from every chunk worker at once; some tray backends do not
+        # survive that. Never taken while self.lock is held, and never takes it.
+        self._icon_lock = threading.Lock()
         self.icon: pystray.Icon | None = None
         self.input_devices = self._get_input_devices()
         self.device_name = load_input_device_name()
@@ -640,6 +832,17 @@ class BlurtApp:
             AwakeKeeper() if sys.platform == "win32" else None
         )
         self.pending_transcriptions = 0
+        self.chunks_total = 0
+        self.chunks_done = 0
+        self._inflight_spool: set[Path] = set()
+        spooled = self._spooled_files()
+        if spooled:
+            logging.warning(
+                "%d clip(s) left in the spool %s by an earlier failure; "
+                "retry them from the tray menu",
+                len(spooled),
+                SPOOL_DIR,
+            )
         logging.info(
             "BlurtApp initialized with %d input devices, model=%s, language=%s, awake_available=%s",
             len(self.input_devices),
@@ -683,24 +886,45 @@ class BlurtApp:
         logging.warning("Configured input device %r is not connected; using system default", name)
         return None
 
-    def _create_icon_image(self, color: tuple[int, int, int]) -> Image.Image:
+    def _create_icon_image(
+        self, color: tuple[int, int, int], progress: float | None = None
+    ) -> Image.Image:
         img = Image.new("RGBA", (64, 64), (0, 0, 0, 0))
         draw = ImageDraw.Draw(img)
-        draw.ellipse([8, 8, 56, 56], fill=color)
+        if progress is None:
+            draw.ellipse([8, 8, 56, 56], fill=color)
+            return img
+        # Dim disc for the whole clip, full colour for the finished fraction,
+        # filling clockwise from 12 o'clock (Pillow measures from 3 o'clock).
+        dim = tuple(round(c * 0.45) for c in color)
+        draw.ellipse([8, 8, 56, 56], fill=dim)
+        progress = min(1.0, max(0.0, progress))
+        if progress > 0:
+            draw.pieslice([8, 8, 56, 56], -90, -90 + 360 * progress, fill=color)
         return img
 
     def _update_icon(self):
-        if self.icon:
+        if not self.icon:
+            return
+        with self._icon_lock:
+            progress = None
+            # One read of each counter: another thread's finally clause can zero
+            # both between two reads, and a fraction over zero raises.
+            done, total = self.chunks_done, self.chunks_total
             if self.recording:
                 color = (220, 40, 40)  # red
                 state = "Recording..."
             elif self.pending_transcriptions > 0:
                 color = (40, 100, 220)  # blue
-                state = "Transcribing..."
+                if total > 1:
+                    state = f"Transcribing {done}/{total}..."
+                    progress = done / total
+                else:
+                    state = "Transcribing..."
             else:
                 color = (120, 120, 120)  # gray
                 state = "Ready"
-            self.icon.icon = self._create_icon_image(color)
+            self.icon.icon = self._create_icon_image(color, progress)
             self.icon.title = f"{APP_NAME} - {state}"
             self.icon.update_menu()
 
@@ -749,18 +973,24 @@ class BlurtApp:
             return f"API key: {provider_label} (missing)"
         return f"API key: {provider_label} (…{key[-4:]})"
 
+    def _require_api_key(self, action: str) -> bool:
+        if self._current_api_key():
+            return True
+        provider = self._provider_for_model(self.transcription_model)
+        key_hint = PROVIDER_KEY_HINTS.get(provider, f"set the {provider} API key")
+        logging.error(
+            "%s blocked: model=%s provider=%s has no API key; "
+            "%s or select a model with an available key",
+            action,
+            self.transcription_model,
+            provider,
+            key_hint,
+        )
+        self.platform.notify("Error", f"No {provider} API key; {key_hint}.")
+        return False
+
     def _start_recording(self):
-        if not self._current_api_key():
-            provider = self._provider_for_model(self.transcription_model)
-            key_hint = PROVIDER_KEY_HINTS.get(provider, f"set the {provider} API key")
-            logging.error(
-                "Recording blocked: model=%s provider=%s has no API key; "
-                "%s or select a model with an available key",
-                self.transcription_model,
-                provider,
-                key_hint,
-            )
-            self.platform.notify("Error", f"No {provider} API key; {key_hint}.")
+        if not self._require_api_key("Recording"):
             return
         self.audio_frames = []
         try:
@@ -863,66 +1093,358 @@ class BlurtApp:
         dump_capture("sent", sent)
         return sent
 
-    def _transcribe(self, audio_data: np.ndarray):
-        self.platform.notify(
-            "Transcribing",
-            f"Using {get_model_label(self.transcription_model)} ({self.transcription_language})",
+    def _transcribe(
+        self,
+        audio_data: np.ndarray,
+        spool_path: Path | None = None,
+        collect: list[str] | None = None,
+    ):
+        """Transcribe one clip. With `collect`, the text is appended there
+        instead of being handed to the user: a retry run copies everything it
+        recovered in one go rather than overwriting the clipboard per clip."""
+        ranges = split_at_silence(audio_data)
+        detail = (
+            f"Using {get_model_label(self.transcription_model)} "
+            f"({self.transcription_language})"
         )
-        logging.info("Starting transcription: samples=%d", len(audio_data))
-
-        buffer = io.BytesIO()
-        wavfile.write(buffer, SAMPLE_RATE, audio_data)
-        wav_bytes = buffer.getvalue()
-        logging.info("Encoded WAV in memory: %d bytes", len(wav_bytes))
+        if len(ranges) > 1:
+            detail = f"{detail} in {len(ranges)} chunks"
+        self.platform.notify("Transcribing", detail)
+        with self.lock:
+            self.chunks_total += len(ranges)
+        self._update_icon()
 
         try:
-            if self._provider_for_model(self.transcription_model) == "openrouter":
-                result = self._transcribe_openrouter(wav_bytes)
+            if len(ranges) == 1:
+                buffer = io.BytesIO()
+                wavfile.write(buffer, SAMPLE_RATE, audio_data)
+                wav_bytes = buffer.getvalue()
+                logging.info("Encoded WAV in memory: %d bytes", len(wav_bytes))
+                try:
+                    text = self._request_transcript(
+                        wav_bytes, len(audio_data) / SAMPLE_RATE
+                    )
+                finally:
+                    self._chunk_finished()
+                self._hand_over(text, collect)
+                self._discard_spool(spool_path)
             else:
-                result = self._transcribe_openai(wav_bytes)
-            text = result.get("text", "").lstrip()
-            logging.info("Transcription text length: %d", len(text))
-            if "usage" in result:
-                logging.info("Transcription usage: %s", result["usage"])
-
-            if not text:
-                error_msg = result.get("error", {}).get("message", "Unknown error")
-                logging.error("Transcription response did not include text: %s", result)
-                self.platform.notify("Error", f"Transcription failed: {error_msg}")
-                return
-
-            if text.lower().startswith(AGENT_PREFIX):
-                task = text[len(AGENT_PREFIX):].lstrip(" ,.:;-")
-                if task:
-                    pyperclip.copy(task)
-                    try:
-                        self.platform.dispatch(task)
-                    except Exception as e:
-                        self.platform.notify("Dispatch Error", str(e))
-                    preview = task[:50] + ("..." if len(task) > 50 else "")
-                    self.platform.notify("Dispatched", preview)
-                    logging.info("Dispatched transcription task with %d characters", len(task))
+                texts, errors = self._transcribe_chunks(audio_data, ranges)
+                if errors:
+                    self._deliver_partial(
+                        audio_data, ranges, texts, errors, spool_path, collect
+                    )
                 else:
-                    pyperclip.copy(text)
-                    self.platform.notify("Error", f"No task after '{AGENT_PREFIX}'")
-                    logging.warning("Agent prefix detected with no task")
-            else:
-                pyperclip.copy(text)
-                preview = text[:50] + ("..." if len(text) > 50 else "")
-                self.platform.notify("Copied", preview)
-                logging.info("Copied transcription to clipboard")
+                    self._hand_over(" ".join(text.strip() for text in texts), collect)
+                    self._discard_spool(spool_path)
 
+        except TranscriptionError as e:
+            self._report_failure(str(e), spool_path)
         except requests.RequestException as e:
             logging.exception("API request failed")
-            self.platform.notify("Error", f"API request failed: {e}")
+            status = rejected_status(e)
+            if status is None:
+                self._report_failure(f"API request failed: {e}", spool_path)
+            else:
+                logging.error(
+                    "Request rejected with HTTP %d: %s", status, response_snippet(e)
+                )
+                self._discard_spool(spool_path, f"Request rejected with HTTP {status}")
+                self.platform.notify(
+                    "Error",
+                    f"API request failed: {e} — audio NOT kept, the request was "
+                    f"rejected (HTTP {status}).",
+                )
         except Exception as e:
             logging.exception("Unexpected transcription failure")
-            self.platform.notify("Error", f"Unexpected transcription failure: {e}")
+            self._report_failure(f"Unexpected transcription failure: {e}", spool_path)
         finally:
-            self.pending_transcriptions -= 1
+            with self.lock:
+                self.pending_transcriptions -= 1
+                if self.pending_transcriptions == 0:
+                    self.chunks_total = self.chunks_done = 0
+                if spool_path is not None:
+                    self._inflight_spool.discard(spool_path)
             self._update_icon()
 
-    def _transcribe_openai(self, wav_bytes: bytes) -> dict:
+    def _chunk_finished(self):
+        with self.lock:
+            self.chunks_done += 1
+        try:
+            self._update_icon()
+        except Exception:
+            # A tray backend that cannot draw must not turn a transcribed chunk
+            # into a failed one.
+            logging.exception("Could not update the tray icon after a finished chunk")
+
+    def _hand_over(self, text: str, collect: list[str] | None):
+        """Give the transcript to the user, or to the retry run collecting them."""
+        if collect is None:
+            self._deliver(text)
+        else:
+            collect.append(text)
+
+    def _deliver(self, text: str):
+        if text.lower().startswith(AGENT_PREFIX):
+            task = text[len(AGENT_PREFIX):].lstrip(" ,.:;-")
+            if task:
+                pyperclip.copy(task)
+                try:
+                    self.platform.dispatch(task)
+                except Exception as e:
+                    self.platform.notify("Dispatch Error", str(e))
+                preview = task[:50] + ("..." if len(task) > 50 else "")
+                self.platform.notify("Dispatched", preview)
+                logging.info("Dispatched transcription task with %d characters", len(task))
+            else:
+                pyperclip.copy(text)
+                self.platform.notify("Error", f"No task after '{AGENT_PREFIX}'")
+                logging.warning("Agent prefix detected with no task")
+        else:
+            pyperclip.copy(text)
+            preview = text[:50] + ("..." if len(text) > 50 else "")
+            self.platform.notify("Copied", preview)
+            logging.info("Copied transcription to clipboard")
+
+    def _transcribe_chunks(
+        self, audio_data: np.ndarray, ranges: list[tuple[int, int]]
+    ) -> tuple[list[str | None], dict[int, Exception]]:
+        """Upload every chunk in parallel; text per chunk, plus what went wrong
+        for each missing one. The clip is already recorded, so latency is all
+        that is left to save, and one dead chunk must not cost the other nine.
+        The exception itself is kept, not just its message: whether the audio is
+        worth spooling depends on why the request failed."""
+        texts: list[str | None] = [None] * len(ranges)
+        errors: dict[int, Exception] = {}
+
+        def upload(index: int) -> str:
+            start, end = ranges[index]
+            chunk = audio_data[start:end]
+            buffer = io.BytesIO()
+            wavfile.write(buffer, SAMPLE_RATE, chunk)
+            wav_bytes = buffer.getvalue()
+            logging.info(
+                "Encoded chunk %d of %d in memory: %d bytes, %.1fs",
+                index + 1,
+                len(ranges),
+                len(wav_bytes),
+                len(chunk) / SAMPLE_RATE,
+            )
+            try:
+                return self._request_transcript(wav_bytes, len(chunk) / SAMPLE_RATE)
+            finally:
+                self._chunk_finished()
+
+        with ThreadPoolExecutor(max_workers=CHUNK_WORKERS) as pool:
+            futures = [pool.submit(upload, index) for index in range(len(ranges))]
+        for index, future in enumerate(futures):
+            try:
+                texts[index] = future.result()
+            except Exception as e:
+                errors[index] = e
+                logging.exception(
+                    "Chunk %d of %d failed (%.1fs at %.1fs into the clip)",
+                    index + 1,
+                    len(ranges),
+                    (ranges[index][1] - ranges[index][0]) / SAMPLE_RATE,
+                    ranges[index][0] / SAMPLE_RATE,
+                )
+        return texts, errors
+
+    def _deliver_partial(
+        self,
+        audio_data: np.ndarray,
+        ranges: list[tuple[int, int]],
+        texts: list[str | None],
+        errors: dict[int, Exception],
+        spool_path: Path | None,
+        collect: list[str] | None = None,
+    ):
+        """Hand over what came back and keep only the audio that did not. The
+        transcript has holes in it, so it goes to the clipboard for the user to
+        read — never to an agent, which cannot see what is missing."""
+        for index in sorted(errors):
+            logging.error(
+                "Chunk %d of %d has no transcript: %s",
+                index + 1,
+                len(ranges),
+                error_text(errors[index]),
+            )
+        if len(errors) == len(ranges) and spool_path is not None and spool_path.exists():
+            logging.error("Every chunk failed; keeping the whole clip at %s", spool_path)
+            kept_note = "audio kept, retry from the tray menu"
+        else:
+            stem = spool_path.stem if spool_path is not None else spool_stem()
+            kept = unwritten = 0
+            for index in sorted(errors):
+                status = rejected_status(errors[index])
+                if status is not None:
+                    logging.error(
+                        "Not keeping chunk %d: rejected with HTTP %d, so re-uploading "
+                        "it can only be rejected again: %s",
+                        index + 1,
+                        status,
+                        response_snippet(errors[index]),
+                    )
+                    continue
+                start, end = ranges[index]
+                if spool_chunk(audio_data[start:end], stem, index + 1) is None:
+                    unwritten += 1
+                else:
+                    kept += 1
+            if unwritten == 0:
+                # Every chunk worth keeping is in the spool under its own name;
+                # the whole clip would only make the retry re-upload good audio.
+                self._discard_spool(spool_path)
+                kept_note = (
+                    f"{kept} of them kept, retry from the tray menu"
+                    if kept
+                    else "audio NOT kept, the request was rejected"
+                )
+            elif spool_path is not None and spool_path.exists():
+                logging.error(
+                    "Keeping the whole clip at %s: %d failed chunk(s) could not be "
+                    "spooled on their own",
+                    spool_path,
+                    unwritten,
+                )
+                kept_note = "whole clip kept, retry from the tray menu"
+            else:
+                logging.error(
+                    "%d failed chunk(s) could not be spooled and there is no whole "
+                    "clip to fall back on; their audio is gone",
+                    unwritten,
+                )
+                kept_note = f"audio of {unwritten} of them could NOT be kept"
+        if len(errors) == len(ranges):
+            # Nothing came back, so there is no partial transcript to hand over.
+            self.platform.notify(
+                "Error",
+                f"All {len(ranges)} chunks failed: {error_text(errors[min(errors)])} — "
+                f"{kept_note}.",
+            )
+            return
+
+        pieces: list[str] = []
+        for text in texts:
+            if text:
+                pieces.append(text.strip())
+            elif not pieces or pieces[-1] != "[…]":
+                pieces.append("[…]")
+        partial = " ".join(pieces)
+        message = f"{len(errors)} of {len(ranges)} chunks failed — {kept_note}"
+        if collect is not None:
+            collect.append(partial)
+            logging.info(
+                "Collected partial transcription for the retry run: %d characters",
+                len(partial),
+            )
+        else:
+            pyperclip.copy(partial)
+            if partial.lower().startswith(AGENT_PREFIX):
+                message = (
+                    f"{message}. Copied instead of dispatched: the transcript has holes"
+                )
+                logging.warning("Not dispatching a partial transcript; copied it instead")
+            logging.info(
+                "Copied partial transcription to clipboard: %d characters", len(partial)
+            )
+        self.platform.notify("Partial", message)
+
+    def _request_transcript(self, wav_bytes: bytes, seconds: float) -> str:
+        """Upload one WAV and return its text, raising if the API gave us none."""
+        timeout = transcription_timeout(seconds)
+        logging.info(
+            "Starting transcription: %.1fs of audio, connect_timeout=%.0fs read_timeout=%.0fs",
+            seconds,
+            timeout[0],
+            timeout[1],
+        )
+        if self._provider_for_model(self.transcription_model) == "openrouter":
+            result = self._transcribe_openrouter(wav_bytes, timeout)
+        else:
+            result = self._transcribe_openai(wav_bytes, timeout)
+        text = result.get("text", "").lstrip()
+        logging.info("Transcription text length: %d", len(text))
+        if "usage" in result:
+            logging.info("Transcription usage: %s", result["usage"])
+        if not text:
+            error_msg = result.get("error", {}).get("message", "Unknown error")
+            logging.error("Transcription response did not include text: %s", result)
+            raise TranscriptionError(f"Transcription failed: {error_msg}")
+        return text
+
+    def _report_failure(self, message: str, spool_path: Path | None):
+        if spool_path is not None and spool_path.exists():
+            logging.error("Keeping audio at %s after failure: %s", spool_path, message)
+            message = f"{message} — audio kept, retry from the tray menu."
+        self.platform.notify("Error", message)
+
+    def _discard_spool(self, spool_path: Path | None, reason: str = "Transcript delivered"):
+        if spool_path is None:
+            return
+        try:
+            spool_path.unlink(missing_ok=True)
+            logging.info("%s; removed spooled clip %s", reason, spool_path)
+        except OSError:
+            logging.exception("Could not remove spooled clip %s", spool_path)
+
+    def _spooled_files(self) -> list[Path]:
+        """Spooled clips, oldest first (their names are timestamps)."""
+        try:
+            return sorted(SPOOL_DIR.glob("*.wav"))
+        except OSError:
+            logging.exception("Could not list the spool %s", SPOOL_DIR)
+            return []
+
+    def _retryable_files(self) -> list[Path]:
+        """Spooled clips a retry would actually take on: not the one that is
+        being uploaded right now, or the menu offers to retry a clip whose first
+        attempt has not even finished. A stale copy of the in-flight set is fine
+        here — the worker checks it again under the lock."""
+        inflight = set(self._inflight_spool)
+        return [path for path in self._spooled_files() if path not in inflight]
+
+    def _retry_spooled(self, icon=None, item=None):
+        if not self._require_api_key("Retry"):
+            return
+        threading.Thread(target=self._retry_spooled_worker, daemon=True, name="RetrySpool").start()
+
+    def _retry_spooled_worker(self):
+        """Re-upload spooled clips one at a time: they failed once already, and a
+        burst of parallel requests is the least likely thing to fix that. Their
+        transcripts are collected and copied together at the end — one clipboard
+        holds one thing, and a per-clip copy would leave only the last clip."""
+        collected: list[str] = []
+        for path in self._spooled_files():
+            with self.lock:
+                if path in self._inflight_spool:
+                    logging.info("Not retrying %s: it is being transcribed right now", path)
+                    continue
+                self._inflight_spool.add(path)
+            audio_data = load_spooled_capture(path)
+            if audio_data is None:
+                with self.lock:
+                    self._inflight_spool.discard(path)
+                continue
+            with self.lock:
+                self.pending_transcriptions += 1
+            self._update_icon()
+            logging.info("Retrying spooled clip %s", path)
+            self._transcribe(audio_data, path, collected)
+        if not collected:
+            return
+        pyperclip.copy("\n\n".join(collected))
+        # Never dispatched: a retried clip may be one part of a longer recording,
+        # and an agent prefix on it would send a truncated task.
+        logging.info(
+            "Copied %d retried transcript(s) to the clipboard; retries are copied, "
+            "never dispatched",
+            len(collected),
+        )
+        self.platform.notify("Copied", f"Copied {len(collected)} retried transcript(s)")
+
+    def _transcribe_openai(self, wav_bytes: bytes, timeout: tuple[float, float]) -> dict:
         data = {
             "model": self.transcription_model,
             "language": self.transcription_language,
@@ -935,13 +1457,13 @@ class BlurtApp:
             headers={"Authorization": f"Bearer {self.api_keys['openai']}"},
             files={"file": ("blurt.wav", wav_bytes, "audio/wav")},
             data=data,
-            timeout=30,
+            timeout=timeout,
         )
         self._log_transcription_response(response)
         response.raise_for_status()
         return response.json()
 
-    def _transcribe_openrouter(self, wav_bytes: bytes) -> dict:
+    def _transcribe_openrouter(self, wav_bytes: bytes, timeout: tuple[float, float]) -> dict:
         audio_b64 = base64.b64encode(wav_bytes).decode("ascii")
         response = self.session.post(
             OPENROUTER_TRANSCRIPTIONS_URL,
@@ -955,7 +1477,7 @@ class BlurtApp:
                 "input_audio": {"data": audio_b64, "format": "wav"},
                 "language": self.transcription_language,
             },
-            timeout=30,
+            timeout=timeout,
         )
         self._log_transcription_response(response)
         response.raise_for_status()
@@ -978,10 +1500,15 @@ class BlurtApp:
             else:
                 audio_data = self._stop_recording()
                 if audio_data is not None:
+                    spool_path = spool_capture(audio_data)
+                    if spool_path is not None:
+                        self._inflight_spool.add(spool_path)
                     self.pending_transcriptions += 1
                     self._update_icon()
                     t = threading.Thread(
-                        target=self._transcribe, args=(audio_data,), daemon=True
+                        target=self._transcribe,
+                        args=(audio_data, spool_path),
+                        daemon=True,
                     )
                     t.start()
                 else:
@@ -1131,6 +1658,11 @@ class BlurtApp:
             pystray.MenuItem("Model", pystray.Menu(*model_items)),
             pystray.MenuItem(lambda item: self._api_key_label(), None, enabled=False),
             pystray.MenuItem("Language", pystray.Menu(*language_items)),
+            pystray.MenuItem(
+                lambda item: f"Retry failed transcriptions ({len(self._retryable_files())})",
+                self._retry_spooled,
+                enabled=lambda item: len(self._retryable_files()) > 0,
+            ),
             pystray.MenuItem("Show Logs", self._show_logs),
             *awake_items,
             pystray.Menu.SEPARATOR,