diff --git a/CLAUDE.md b/CLAUDE.md
index 9a9ab05..264aa08 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -93,22 +93,69 @@ Voices are interleaved for perceptual diversity: American female → British mal
 
 ## `speak()` Progress Lifecycle
 
-`speak()` blocks until playback finishes, reporting progress throughout:
+`speak()` blocks until playback finishes, reporting progress throughout. Each progress notification includes a `message` field that LLM clients can read to understand the current phase.
 
-| Progress | Phase |
-|----------|-------|
-| 5% | Entry tone played — audible "I heard you" |
-| 30% | Synthesis complete |
-| 35% | Enqueued for playback |
-| 35-99% | Playing — progress tracks elapsed time vs expected duration |
-| 100% | Playback finished |
+| Progress | Phase | Message |
+|----------|-------|---------|
+| 5% | Entry tone played — audible "I heard you" | `Entry tone` |
+| 30% | Synthesis complete | `Synthesizing...` |
+| 35% | Enqueued for playback | `Playing audio — you can continue working` |
+| 35-99% | Playing — progress tracks elapsed time vs expected duration | `Playing audio — you can continue working` |
+| 100% | Playback finished | `Playback complete` |
 
 MCP-aware clients see a live progress bar. The entry tone fires before synthesis, covering the 1-3s latency gap.
 
+### Concurrency guidance
+
+The `speak()` call completes when playback finishes (10-60s for typical text), but the audio plays through physical speakers — the return value doesn't feed into subsequent reasoning. LLM clients like Claude Code can call `speak()` alongside other tools in the same message. The server instructions and tool docstring explicitly encourage this. Tool annotations (`openWorldHint=True`, `idempotentHint=True`) provide structured signals to clients that support them.
+
 `speech_status(speech_id)` is still available for checking outcomes after the fact. Possible statuses: `completed`, `playing`, `queued`, `unknown`.
 
 Outcomes are stored in a bounded ring (last 100 items) — old entries are evicted automatically.
 
+## Chunked Synthesis (Pipelined Playback)
+
+Long texts (>= 20 words with sentence boundaries) are automatically split into sentence-sized chunks and pipelined — synthesis of chunk N+1 overlaps playback of chunk N.
+
+```
+Single-shot:  [---12s synthesis---][----------48s playback----------]  First audio at T+12s
+Chunked:      [~1s synth][play 1][~1s synth][play 2][~1s synth][play 3]...  First audio at T+1s
+```
+
+### Why no gaps
+
+Kokoro synthesizes ~4x realtime on CPU, so synthesis always outpaces playback. `pw-play` adds ~10ms startup per chunk — imperceptible. Slower engines (Orpheus) may have brief gaps but still beat the full-synthesis-first approach.
+
+### Short text bypass
+
+Texts under 20 words or without sentence boundaries (`.!?` followed by whitespace) take the single-shot path — zero overhead, identical to pre-chunking behavior.
+
+### Tone behavior
+
+- Entry tone plays once at the start (before first chunk synthesis)
+- Exit/standby tones are suppressed between chunks (`suppress_exit_tone` flag on `_WorkItem`)
+- Final chunk plays the normal exit tone (roger) or standby tone
+
+### Cancellation in chunked mode
+
+- **Explicit `cancel_speech(speech_id)`** — cancels the returned speech_id (the final chunk). Already-playing earlier chunks finish naturally.
+- **MCP disconnect** — the synthesis loop stops (remaining chunks aren't synthesized). Already-enqueued chunks play through.
+
+### Progress lifecycle (chunked)
+
+| Progress | Phase | Message |
+|----------|-------|---------|
+| 5% | Entry tone played | `Entry tone` |
+| 5-30% | Synthesis progress across all chunks | `Synthesizing chunk N/M...` |
+| 35% | All chunks enqueued | `Playing audio — you can continue working` |
+| 35-99% | Playing — tracks elapsed time vs total duration | `Playing audio — you can continue working` |
+| 100% | Final chunk playback finished | `Playback complete` |
+
+### Files
+
+- `server.py` — `split_text()`, `_speak_single()`, `_speak_chunked()`, `_await_with_progress()`
+- `queue.py` — `suppress_exit_tone` field on `_WorkItem`
+
 ## Cancellation
 
 Speech can be cancelled two ways:
diff --git a/src/tts_mcp/queue.py b/src/tts_mcp/queue.py
index 4ccdf3e..4195659 100644
--- a/src/tts_mcp/queue.py
+++ b/src/tts_mcp/queue.py
@@ -41,6 +41,7 @@ class _WorkItem:
     future: asyncio.Future = field(compare=False)
     speech_id: str = field(default="", compare=False)
     enqueued_at: float = field(default_factory=time.time, compare=False)
+    suppress_exit_tone: bool = field(default=False, compare=False)
 
 
 class SpeechQueue:
@@ -213,15 +214,17 @@ class SpeechQueue:
                 )
 
                 # Play exit tone — "standby" if more queued, "roger" if done
-                exit_t = (
-                    self._standby_tone if self._queue.qsize() > 0
-                    else self._exit_tone
-                )
-                if exit_t:
-                    try:
-                        await play_audio(exit_t, expected_seconds=0.3)
-                    except PlaybackError:
-                        pass  # Non-fatal
+                # suppress_exit_tone skips tones between chunks of the same message
+                if not item.suppress_exit_tone:
+                    exit_t = (
+                        self._standby_tone if self._queue.qsize() > 0
+                        else self._exit_tone
+                    )
+                    if exit_t:
+                        try:
+                            await play_audio(exit_t, expected_seconds=0.3)
+                        except PlaybackError:
+                            pass  # Non-fatal
 
                 self._resolve_outcome(item, {
                     "played": True,
@@ -282,6 +285,7 @@ class SpeechQueue:
         self,
         result: TTSResult,
         priority: Priority = Priority.NORMAL,
+        suppress_exit_tone: bool = False,
     ) -> dict:
         """Enqueue a TTSResult for playback. Returns immediately with enqueue metadata.
 
@@ -308,6 +312,7 @@ class SpeechQueue:
             result=result,
             future=future,
             speech_id=speech_id,
+            suppress_exit_tone=suppress_exit_tone,
         )
 
         try:
diff --git a/src/tts_mcp/server.py b/src/tts_mcp/server.py
index fd66584..7580928 100644
--- a/src/tts_mcp/server.py
+++ b/src/tts_mcp/server.py
@@ -1,6 +1,7 @@
 """FastMCP 3.0 server — tools, lifespan, and resource definitions."""
 
 import asyncio
+import re
 import sys
 import time
 from contextlib import asynccontextmanager
@@ -9,6 +10,7 @@ from typing import Literal
 
 from fastmcp import Context, FastMCP
 from fastmcp.server.dependencies import CurrentContext
+from mcp.types import ToolAnnotations
 
 from .audio import play_audio
 from .engines.base import TTSEngine
@@ -115,9 +117,11 @@ async def app_lifespan(server: FastMCP):
 mcp = FastMCP(
     "tts-mcp",
     instructions=(
-        "Multi-engine text-to-speech server. Use 'speak' to synthesize and enqueue audio "
-        "for playback through the host speakers — returns immediately with a speech_id. "
-        "Use 'speech_status' to check if playback completed, is in progress, or still queued. "
+        "Multi-engine text-to-speech server. Use 'speak' to synthesize and play audio "
+        "through the host speakers. The call completes when playback finishes, but you "
+        "can safely call speak alongside other tools — audio plays through physical "
+        "speakers and doesn't need your attention. Progress updates arrive every second "
+        "during playback. Use 'speech_status' to check outcomes after the fact. "
         "Use 'generate_audio' to synthesize without playing. "
         "Engines: kokoro (fast ONNX, ~50 voices), piper (Wyoming/Docker), "
         "orpheus (LLM via llama-server, supports <laugh> etc.). "
@@ -142,6 +146,43 @@ async def _play_tone(tone_path: Path) -> None:
         print(f"  Entry tone failed (non-fatal): {e}", file=sys.stderr)
 
 
+_CHUNK_WORD_THRESHOLD = 20  # texts shorter than this bypass chunking
+
+
+def split_text(text: str) -> list[str]:
+    """Split text into sentence-sized chunks for pipelined synthesis.
+
+    Splits on sentence-ending punctuation (.!?) followed by whitespace.
+    Merges short fragments (< 5 words) with their neighbor.
+    Returns [text] unchanged if under the word threshold.
+    """
+    words = text.split()
+    if len(words) < _CHUNK_WORD_THRESHOLD:
+        return [text]
+
+    # Split on sentence boundaries — require uppercase after split to avoid
+    # false positives on abbreviations (Dr.), decimals (3.0), URLs, etc.
+    raw = re.split(r"(?<=[.!?])\s+(?=[A-Z])", text.strip())
+    if len(raw) <= 1:
+        return [text]
+
+    # Merge short fragments (< 5 words) with next chunk.
+    # First chunk is allowed to be short — minimizes time-to-first-audio.
+    chunks: list[str] = [raw[0]]
+    for fragment in raw[1:]:
+        if len(chunks[-1].split()) < 5:
+            chunks[-1] = chunks[-1] + " " + fragment
+        else:
+            chunks.append(fragment)
+
+    # If the last chunk is very short, merge it into its predecessor
+    if len(chunks) > 1 and len(chunks[-1].split()) < 5:
+        tail = chunks.pop()
+        chunks[-1] = chunks[-1] + " " + tail
+
+    return chunks
+
+
 async def _resolve_project_voice(
     ctx: Context,
     engine_name: str,
@@ -171,7 +212,196 @@ async def _resolve_project_voice(
 # Tools
 # ---------------------------------------------------------------------------
 
-@mcp.tool
+async def _speak_single(
+    eng: TTSEngine,
+    engine: str,
+    text: str,
+    voice: str | None,
+    queue: SpeechQueue,
+    entry_tone: Path | None,
+    priority: Priority,
+    ctx: Context,
+) -> dict:
+    """Single-shot speak path — synthesize full text, then enqueue.
+
+    Used for short texts (< 20 words) and as the fallback when text has
+    no sentence boundaries.
+    """
+    try:
+        if entry_tone:
+            await _play_tone(entry_tone)
+        await ctx.report_progress(progress=5, total=100, message="Entry tone")
+
+        await ctx.info(f"Synthesizing with {engine}...")
+        result = await eng.synthesize(text, voice)
+        await ctx.report_progress(progress=30, total=100, message="Synthesizing...")
+
+        await ctx.info(f"Synthesized {result.duration_seconds:.1f}s audio, enqueueing...")
+        enqueue_result = await queue.enqueue(result, priority=priority)
+
+        if not enqueue_result.get("queued"):
+            return enqueue_result
+
+        speech_id = enqueue_result["speech_id"]
+        duration = result.duration_seconds
+        await ctx.report_progress(
+            progress=35, total=100,
+            message="Playing audio \u2014 you can continue working",
+        )
+
+        await ctx.info("Playing...")
+        # NOTE: Do NOT use asyncio.wait_for() — see CLAUDE.md Python 3.13 pitfall
+        outcome = await _await_with_progress(queue, speech_id, duration, ctx, 35)
+
+        await ctx.report_progress(progress=100, total=100, message="Playback complete")
+        return outcome
+
+    except asyncio.CancelledError:
+        # speak() was cancelled (server shutdown or MCP client disconnect).
+        # Do NOT cancel the consumer — let it finish the current audio.
+        # Shutdown: queue.stop() in the lifespan finalizer handles graceful drain.
+        # Client cancel: use cancel_speech(speech_id) for explicit mid-playback stop.
+        raise
+
+
+async def _speak_chunked(
+    eng: TTSEngine,
+    engine: str,
+    chunks: list[str],
+    voice: str | None,
+    queue: SpeechQueue,
+    entry_tone: Path | None,
+    priority: Priority,
+    ctx: Context,
+) -> dict:
+    """Chunked speak path — pipeline synthesis with playback.
+
+    Synthesizes sentence chunks one at a time and enqueues each immediately.
+    Playback of chunk N overlaps synthesis of chunk N+1. Non-final chunks
+    suppress exit/standby tones for seamless playback.
+    """
+    n_chunks = len(chunks)
+    total_duration = 0.0
+    all_speech_ids: list[str] = []
+    first_enqueue_time: float | None = None
+
+    try:
+        if entry_tone:
+            await _play_tone(entry_tone)
+        await ctx.report_progress(progress=5, total=100, message="Entry tone")
+
+        for i, chunk in enumerate(chunks):
+            is_last = i == n_chunks - 1
+            pct_synth = 5 + int(25 * (i + 1) / n_chunks)  # 5-30% across all chunks
+
+            await ctx.info(f"Synthesizing chunk {i + 1}/{n_chunks} with {engine}...")
+            result = await eng.synthesize(chunk, voice)
+            total_duration += result.duration_seconds
+            await ctx.report_progress(
+                progress=pct_synth, total=100,
+                message=f"Synthesizing chunk {i + 1}/{n_chunks}...",
+            )
+
+            enqueue_result = await queue.enqueue(
+                result,
+                priority=priority,
+                suppress_exit_tone=not is_last,
+            )
+
+            if not enqueue_result.get("queued"):
+                # Queue full mid-message — already-enqueued chunks play through
+                if all_speech_ids:
+                    await ctx.info(f"Queue full at chunk {i + 1}/{n_chunks}, waiting for enqueued chunks...")
+                    elapsed = time.time() - first_enqueue_time if first_enqueue_time else 0
+                    remaining = max(total_duration - elapsed, 0.1)
+                    outcome = await _await_with_progress(queue, all_speech_ids[-1], remaining, ctx, 35)
+                    outcome["chunks_enqueued"] = len(all_speech_ids)
+                    outcome["chunks_total"] = n_chunks
+                    return outcome
+                return enqueue_result
+
+            all_speech_ids.append(enqueue_result["speech_id"])
+            if first_enqueue_time is None:
+                first_enqueue_time = time.time()
+
+        # All chunks enqueued — wait for final chunk to finish playing
+        if not all_speech_ids:
+            return {"error": "No chunks were successfully enqueued", "chunks_total": n_chunks}
+
+        await ctx.report_progress(
+            progress=35, total=100,
+            message="Playing audio \u2014 you can continue working",
+        )
+        await ctx.info(f"Playing {n_chunks} chunks ({total_duration:.1f}s total)...")
+
+        # Subtract time already elapsed since first chunk started playing
+        elapsed = time.time() - first_enqueue_time if first_enqueue_time else 0
+        remaining = max(total_duration - elapsed, 0.1)
+        outcome = await _await_with_progress(queue, all_speech_ids[-1], remaining, ctx, 35)
+        await ctx.report_progress(progress=100, total=100, message="Playback complete")
+
+        # Check for partial failures in earlier chunks
+        failed_chunks = []
+        for idx, sid in enumerate(all_speech_ids[:-1]):
+            chunk_status = queue.get_status(sid)
+            if chunk_status.get("status") == "completed" and not chunk_status.get("played", True):
+                failed_chunks.append(idx + 1)
+
+        outcome["chunks"] = n_chunks
+        outcome["total_duration_seconds"] = total_duration
+        if failed_chunks:
+            outcome["partial_failure"] = True
+            outcome["failed_chunks"] = failed_chunks
+        return outcome
+
+    except asyncio.CancelledError:
+        # speak() was cancelled (server shutdown or MCP client disconnect).
+        # Do NOT cancel the consumer — let already-enqueued chunks play through.
+        # Shutdown: queue.stop() in the lifespan finalizer handles graceful drain.
+        # Client cancel: use cancel_speech(speech_id) for explicit mid-playback stop.
+        raise
+
+
+async def _await_with_progress(
+    queue: SpeechQueue,
+    speech_id: str,
+    duration: float,
+    ctx: Context,
+    base_pct: int,
+) -> dict:
+    """Await playback completion with a progress ticker.
+
+    Uses a background task for progress — NOT asyncio.wait_for polling
+    (see CLAUDE.md for the Python 3.13 pitfall).
+    """
+    async def _progress_ticker():
+        t0 = time.time()
+        while True:
+            await asyncio.sleep(0.5)
+            elapsed = time.time() - t0
+            pct = min(base_pct + int((99 - base_pct) * elapsed / max(duration, 0.1)), 99)
+            await ctx.report_progress(
+                progress=pct, total=100,
+                message="Playing audio \u2014 you can continue working",
+            )
+
+    ticker = asyncio.create_task(_progress_ticker())
+    try:
+        return await queue.wait_for_completion(speech_id)
+    finally:
+        ticker.cancel()
+        try:
+            await ticker
+        except asyncio.CancelledError:
+            pass
+
+
+@mcp.tool(annotations=ToolAnnotations(
+    readOnlyHint=False,
+    destructiveHint=False,
+    idempotentHint=True,
+    openWorldHint=True,
+))
 async def speak(
     text: str,
     engine: ENGINE_NAMES = "kokoro",
@@ -182,8 +412,14 @@ async def speak(
 ) -> dict:
     """Synthesize text and play it through the host speakers.
 
-    Blocks until playback finishes, reporting progress throughout:
-    entry tone → synthesis → queued → playing → done.
+    Audio plays through physical speakers — you don't need to wait for the
+    result to continue your work. Feel free to call this alongside other tools
+    in the same message. Progress notifications report playback status every
+    second.
+
+    Long texts are automatically split into sentences and pipelined — the
+    first sentence plays within ~1-2s while remaining sentences synthesize
+    in the background.
 
     Audio is queued so agents don't talk over each other. Urgent messages
     jump ahead of normal-priority items.
@@ -205,70 +441,15 @@ async def speak(
         ctx, engine, eng, voice, text, voice_cache, project,
     )
 
-    speech_id = None
-    try:
-        # Entry tone — audible "I heard you" before synthesis begins
-        if entry_tone:
-            await _play_tone(entry_tone)
-        await ctx.report_progress(progress=5, total=100)
+    priority = Priority.URGENT if urgent else Priority.NORMAL
 
-        # Synthesize audio (multiple agents can synthesize simultaneously)
-        await ctx.info(f"Synthesizing with {engine}...")
-        result = await eng.synthesize(text, voice)
-        await ctx.report_progress(progress=30, total=100)
-
-        # Enqueue for serialized playback
-        await ctx.info(f"Synthesized {result.duration_seconds:.1f}s audio, enqueueing...")
-        enqueue_result = await queue.enqueue(
-            result,
-            priority=Priority.URGENT if urgent else Priority.NORMAL,
-        )
-
-        if not enqueue_result.get("queued"):
-            return enqueue_result
-
-        speech_id = enqueue_result["speech_id"]
-        duration = result.duration_seconds
-        await ctx.report_progress(progress=35, total=100)
-
-        # Wait for playback with progress via a background ticker.
-        # NOTE: Do NOT use asyncio.wait_for() with the future — Python 3.13's
-        # wait_for cancels its inner task on timeout, and repeated cancel/re-await
-        # on the same Future causes a stale CancelledError to propagate to the
-        # consumer task, killing pw-play mid-sentence.
-        await ctx.info("Playing...")
-
-        async def _progress_ticker():
-            """Send progress updates while playback runs."""
-            t0 = time.time()
-            while True:
-                await asyncio.sleep(0.5)
-                elapsed = time.time() - t0
-                pct = min(35 + int(64 * elapsed / max(duration, 0.1)), 99)
-                await ctx.report_progress(progress=pct, total=100)
-
-        ticker = asyncio.create_task(_progress_ticker())
-        try:
-            outcome = await queue.wait_for_completion(speech_id)
-        finally:
-            ticker.cancel()
-            try:
-                await ticker
-            except asyncio.CancelledError:
-                pass
-
-        await ctx.report_progress(progress=100, total=100)
-        return outcome
-
-    except asyncio.CancelledError:
-        # speak() was cancelled (server shutdown or MCP client disconnect).
-        # Do NOT cancel the consumer — let it finish the current audio.
-        # Shutdown: queue.stop() in the lifespan finalizer handles graceful drain.
-        # Client cancel: use cancel_speech(speech_id) to explicitly stop playback.
-        raise
+    chunks = split_text(text)
+    if len(chunks) <= 1:
+        return await _speak_single(eng, engine, text, voice, queue, entry_tone, priority, ctx)
+    return await _speak_chunked(eng, engine, chunks, voice, queue, entry_tone, priority, ctx)
 
 
-@mcp.tool
+@mcp.tool(annotations=ToolAnnotations(readOnlyHint=True))
 async def speech_status(
     speech_id: str,
     ctx: Context = CurrentContext(),
@@ -285,7 +466,11 @@ async def speech_status(
     return queue.get_status(speech_id)
 
 
-@mcp.tool
+@mcp.tool(annotations=ToolAnnotations(
+    readOnlyHint=False,
+    destructiveHint=True,
+    idempotentHint=True,
+))
 async def cancel_speech(
     speech_id: str,
     ctx: Context = CurrentContext(),
@@ -302,7 +487,11 @@ async def cancel_speech(
     return queue.cancel(speech_id)
 
 
-@mcp.tool
+@mcp.tool(annotations=ToolAnnotations(
+    readOnlyHint=False,
+    destructiveHint=False,
+    idempotentHint=True,
+))
 async def generate_audio(
     text: str,
     engine: ENGINE_NAMES = "kokoro",
@@ -343,7 +532,7 @@ async def generate_audio(
     }
 
 
-@mcp.tool
+@mcp.tool(annotations=ToolAnnotations(readOnlyHint=True))
 async def list_voices(
     engine: ENGINE_NAMES,
     ctx: Context = CurrentContext(),
@@ -364,7 +553,7 @@ async def list_voices(
     return await engines[engine].list_voices()
 
 
-@mcp.tool
+@mcp.tool(annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True))
 async def list_engines(
     ctx: Context = CurrentContext(),
 ) -> list[dict]: