#338: cancel timed-out queued deliveries

memberHerdrSocket was missing from the prose. The #333 worker spotted it and
correctly left it alone as outside its scope.

Fixed by pointing the bullet at COLD_KEYS instead of re-listing its contents,
so the prose and the set cannot drift apart a second time.

fleetd/src/main/java/dev/ltms/fleet/config/ConfigRef.java

@@ -121,10 +121,12 @@ import java.util.function.Supplier;
  *       reload would leave the operator worse off than today. {@link Outcome#split()} names the
  *       key and says which half is which each time, rather than trying to score "how changed" a
  *       mixed key is or handle "both halves changed in one reload" as a special case.</li>
- *   <li><strong>Cold</strong> — cannot change at all under a running daemon: {@code bind:},
- *       {@code herdrSocket:}, {@code broker:} and {@code auth:}. The socket is bound, the broker
+ *   <li><strong>Cold</strong> — cannot change at all under a running daemon. All five of
+ *       {@link #COLD_KEYS}: {@code bind:}, {@code herdrSocket:}, {@code memberHerdrSocket:},
+ *       {@code broker:} and {@code auth:}. The sockets are already connected, the broker
  *       connection is open, and the auth mode decides who may reach the port that is already
- *       listening.</li>
+ *       listening. This bullet omitted {@code memberHerdrSocket:} until fleetd #333 — say "all
+ *       five of COLD_KEYS" rather than re-listing them, so prose and set cannot drift again.</li>
  * </ul>
  *
  * <p><strong>The denominator, measured on 2026-09-04 (fleetd #330; recounted for fleetd #333).</strong>

fleetd/src/main/java/dev/ltms/fleet/inject/Injector.java

@@ -145,8 +145,58 @@ public final class Injector {
         return router != null ? router.agentsFor(target) : agents;
     }
 
+    /** The result of trying to remove an undelivered message from the injector. */
+    public enum Cancellation {
+        CANCELLED,
+        DELIVERED,
+        NOT_DELIVERED
+    }
+
+    /**
+     * An identity handle for one queued delivery. It is the only value accepted by
+     * {@link #cancel(Delivery)}, so a caller cannot cancel a different message with the same target
+     * or text.
+     */
+    public static final class Delivery {
+        private final Pending pending;
+
+        private Delivery(Pending pending) {
+            this.pending = pending;
+        }
+
+        public CompletableFuture<Void> completion() {
+            return pending.delivered;
+        }
+    }
+
     /** A pending message and the future that completes when it has been delivered. */
-    private record Pending(String text, TurnToken token, CompletableFuture<Void> delivered) {
+    private static final class Pending {
+        enum State { QUEUED, DELIVERED, NOT_DELIVERED, CANCELLED }
+
+        final String target;
+        final String text;
+        final TurnToken token;
+        final CompletableFuture<Void> delivered;
+        volatile State state = State.QUEUED; // written under the owning Target monitor
+
+        Pending(String target, String text, TurnToken token, CompletableFuture<Void> delivered) {
+            this.target = target;
+            this.text = text;
+            this.token = token;
+            this.delivered = delivered;
+        }
+
+        String text() {
+            return text;
+        }
+
+        TurnToken token() {
+            return token;
+        }
+
+        CompletableFuture<Void> delivered() {
+            return delivered;
+        }
     }
 
     /** Per-worker delivery state, guarded by its own monitor (single writer per worker). */
@@ -177,15 +227,47 @@ public final class Injector {
      * <p>Uses an atomic map update so a concurrent {@link #drop} cannot slip between "find the
      * target" and "queue the message" and orphan it in a target it just removed.
      */
-    public CompletableFuture<Void> enqueue(String target, String text, TurnToken token) {
+    public Delivery enqueue(String target, String text, TurnToken token) {
         CompletableFuture<Void> delivered = new CompletableFuture<>();
-        Pending p = new Pending(text, token, delivered);
+        Pending p = new Pending(target, text, token, delivered);
         targets.compute(target, (_, existing) -> {
             Target t = (existing != null) ? existing : new Target();
             t.add(p); // synchronized on the Target monitor — atomic with a concurrent drop
             return t;
         });
-        return delivered;
+        return new Delivery(p);
+    }
+
+    /**
+     * Cancel this exact queued delivery. The target monitor serializes this operation with
+     * {@link #onStatus}: if delivery wins that race, this returns {@link Cancellation#DELIVERED}
+     * rather than claiming the message remained queued.
+     */
+    public Cancellation cancel(Delivery delivery) {
+        Pending p = delivery.pending;
+        Target t = targets.get(p.target);
+        if (t == null) {
+            return cancellationOf(p);
+        }
+        synchronized (t) {
+            if (p.state != Pending.State.QUEUED || !t.queue.remove(p)) {
+                return cancellationOf(p);
+            }
+            p.state = Pending.State.CANCELLED;
+            if (isQuiescent(t)) {
+                targets.remove(p.target, t);
+            }
+            return Cancellation.CANCELLED;
+        }
+    }
+
+    private static Cancellation cancellationOf(Pending p) {
+        return p.state == Pending.State.DELIVERED ? Cancellation.DELIVERED : Cancellation.NOT_DELIVERED;
+    }
+
+    private static boolean isQuiescent(Target t) {
+        return t.queue.isEmpty() && !t.awaitingPickup && !t.awaitingCompletion
+                && !t.postTurnPending && !t.awaitingPostTurnPickup && !t.postTurnObserved;
     }
 
     /**
@@ -274,6 +356,7 @@ public final class Injector {
                             try {
                                 agentsFor(target).send(target, p.text());
                                 t.queue.poll();
+                                p.state = Pending.State.DELIVERED;
                                 t.awaitingPickup = true;
                                 t.awaitingCompletion = true;
                                 t.turnObserved = false;
@@ -283,6 +366,7 @@ public final class Injector {
                                 // Delivery failed at herdr; drop the poisoned message and surface it
                                 // rather than blocking the queue behind it.
                                 t.queue.poll();
+                                p.state = Pending.State.NOT_DELIVERED;
                                 sent = p;
                                 sendError = e;
                             }
@@ -293,6 +377,9 @@ public final class Injector {
                             // fail every queued message and release the target (CB-114) instead of
                             // polling it indefinitely with the caller's future never completing.
                             notReady = new ArrayList<>(t.queue);
+                            for (Pending pending : notReady) {
+                                pending.state = Pending.State.NOT_DELIVERED;
+                            }
                             log.warn("readiness grace for {} expired after {} polls ({}s): target never "
                                     + "became deliverable, so failing {} queued message(s) that never "
                                     + "reached its pane",
@@ -340,8 +427,7 @@ public final class Injector {
 
             // Reclaim the entry once the worker is fully quiescent (nothing queued, no pickup or
             // completion awaited), so the map cannot grow without bound across short-lived workers.
-            if (t.queue.isEmpty() && !t.awaitingPickup && !t.awaitingCompletion
-                    && !t.postTurnPending && !t.awaitingPostTurnPickup && !t.postTurnObserved) {
+            if (isQuiescent(t)) {
                 targets.remove(target, t);
             }
         }
@@ -432,6 +518,9 @@ public final class Injector {
         boolean hadDeliveredTurn;
         synchronized (t) {
             pending = new ArrayList<>(t.queue);
+            for (Pending p : pending) {
+                p.state = Pending.State.NOT_DELIVERED;
+            }
             t.queue.clear();
             hadDeliveredTurn = t.awaitingCompletion;
             t.awaitingCompletion = false;

fleetd/src/main/java/dev/ltms/fleet/msg/MessageService.java

@@ -466,8 +466,18 @@ public final class MessageService {
         if (candidates.size() == 1) {
             Task orphan = candidates.get(0);
             if (orphan.future.complete(new Reply(Outcome.REPLIED, content))) {
-                if (orphan.turnId != null) {
-                    asyncTasksByTurn.remove(orphan.turnId, orphan);
+                // fleetd #329 (F3): read orphan.turnId once. It used to be read twice, under no
+                // lock — once for this null check, once as the removal key — the same double-read
+                // shape fleetd #324 fixed in finishAsyncTask. clearAsyncQuestion's unlocked
+                // forgetTurn=true path (ask()'s timeout cleanup) can null the field between the two
+                // reads; capturing it once removes the torn read here too.
+                String turnId = orphan.turnId;
+                if (turnId != null) {
+                    if (replyOrphanTurnIdRaceHookForTest != null) {
+                        // Test-only (fleetd #329, F3): see the field's own javadoc.
+                        replyOrphanTurnIdRaceHookForTest.run();
+                    }
+                    asyncTasksByTurn.remove(turnId, orphan);
                 }
                 count(FleetMetrics.REPLIES, "path", "async-recovered");
                 return true;                   // the ticket itself took it — no inbox stranding at all
@@ -853,16 +863,22 @@ public final class MessageService {
                 if (onAccepted != null) {
                     onAccepted.run();
                 }
-                CompletableFuture<Void> delivered = injector.enqueue(target, content, token);
+                Injector.Delivery delivery = injector.enqueue(target, content, token);
                 try {
                     Rendezvous.Resolution r = reply.get(remainingMillis(deadlineNanos), TimeUnit.MILLISECONDS);
                     return recorded(new Reply(outcomeOf(r.kind()), r.text(), r.turnId()));
                 } catch (TimeoutException e) {
-                    boolean wasDelivered = delivered.isDone() && !delivered.isCompletedExceptionally();
+                    boolean wasDelivered = delivery.completion().isDone()
+                            && !delivery.completion().isCompletedExceptionally();
+                    if (!wasDelivered) {
+                        // The target monitor makes cancellation atomic with onStatus picking this
+                        // Pending up. If pickup won, report TIMED_OUT_WORKING because the text landed.
+                        wasDelivered = injector.cancel(delivery) == Injector.Cancellation.DELIVERED;
+                    }
                     log.debug("send to {} timed out (delivered={})", target, wasDelivered);
                     if (!wasDelivered) {
-                        // CB-640: still sitting in the injector's queue, waiting for the member to
-                        // go idle — record the fact for fleet health (see queuedDeliveries).
+                        // CB-640: record that delivery did not happen for fleet health (see
+                        // queuedDeliveries). The exact Pending was cancelled, so it cannot arrive later.
                         queuedDeliveries.put(target, Boolean.TRUE);
                     }
                     return recorded(new Reply(
@@ -1002,13 +1018,49 @@ public final class MessageService {
                 // Measured when #282 was merged: this guard is DEFENCE IN DEPTH, not the thing
                 // that makes the chained ask work. ask() calls markAsyncQuestion (:860) before
                 // resolveQuestion (:861), so by the time this thread wakes, the task has already
-                // moved to the new turnId and finishAsyncTask(oldTurnId, ...) finds nothing. Removing
-                // this guard alone leaves the test green. Keep it anyway: it mirrors sendAsync's
-                // sibling guard, and that sibling's own comment (:1017) warns the two orderings are
-                // not something to rely on. Do NOT delete it as dead code without re-checking that
-                // ordering, and do not treat it as the sole protection either.
-                if (result.outcome() != Outcome.QUESTION) {
-                    finishAsyncTask(turnId, result);
+                // moved to the new turnId — this outcome check, not a Task lookup, is what tells the
+                // two cases apart (see fleetd #329 below). Removing this guard alone leaves the test
+                // green. Keep it anyway: it mirrors sendAsync's sibling guard, and that sibling's own
+                // comment (:1017) warns the two orderings are not something to rely on. Do NOT delete
+                // it as dead code without re-checking that ordering, and do not treat it as the sole
+                // protection either.
+                //
+                // fleetd #329 (F1): complete the SAME Task object this method already looked up at
+                // :991, rather than re-resolving it from turnId a second time. The old
+                // finishAsyncTask(turnId, result) did its own asyncTasksByTurn.get(turnId) here, and
+                // that second lookup races ask()'s own timeout path: ask()'s ticket.answer().get(...)
+                // can time out (or lose that exact race) at essentially the same instant this method's
+                // rendezvous.answerAsk(turnId, ...) above already succeeded, running
+                // markAskTimedOut + clearAsyncQuestion(turnId, true) with no lock at all — which
+                // forgets turnId (removes it from asyncTasksByTurn, nulls Task.turnId) before this
+                // thread ever gets here. The worker's real reply then arrived, this method's own wait
+                // woke up with it, and the by-turnId lookup found nothing: the async ticket's future
+                // was never completed, so fleet_poll{ticket} stayed PENDING forever even though
+                // answer() itself correctly returned REPLIED. Reusing the reference captured at :991
+                // — before that race window opens — sidesteps the second lookup entirely: it is the
+                // identical Task whatever asyncTasksByTurn or Task.turnId say by the time we reach
+                // this point, so finishAsyncTask(Task, Reply) can still complete its future and detach
+                // it using whatever turnId it now reads. The #282 chained-ask case is unaffected
+                // because it is still gated purely by result.outcome() == QUESTION above, which does
+                // not depend on this lookup — widening what "task" means here cannot complete a ticket
+                // the chained ask deliberately left open.
+                //
+                // A null task is NOT only "this was never an async ticket". That reading was in this
+                // comment when #329 merged and it is wrong. A genuine async ticket also lands here
+                // with task == null, because ask()'s timeout path runs clearAsyncQuestion(turnId,
+                // true) — which drops the asyncTasksByTurn entry — in its catch block, while
+                // rendezvous.closeAsk(turnId) runs later, in its finally. Between those two the ask
+                // is still answerable but the map entry is already gone, so the lookup at :991
+                // returns null and this ticket is never completed. Measured on 2026-09-04: a probe
+                // firing only that first half before answer() runs printed
+                // "answer=REPLIED phase=PENDING reply=null" — the same stranded ticket #329 set out
+                // to fix, one step earlier in the same race. The probe used forgetTurnForTest, which
+                // omits ask()'s markAskTimedOut; that cannot change the outcome, because askTimedOut
+                // is read only by askAnsweredAsyncTasks, and reply() never reaches it while this
+                // method's own waiter is live. So #329 narrows this window rather than closing it.
+                // Open as fleetd #334 — do not read this guard as complete.
+                if (result.outcome() != Outcome.QUESTION && task != null) {
+                    finishAsyncTask(task, result);
                 }
                 return result;
             } catch (TimeoutException e) {
@@ -1059,7 +1111,7 @@ public final class MessageService {
             // this fires exactly once, from whichever path completes it: finishAsyncTask(task, result)
             // below on any non-QUESTION outcome of send() — a worker's fleet_reply, the CB-106
             // completion fallback, a CB-109 wedge, TIMED_OUT, BUSY, or BACKEND_EXHAUSTED — the same
-            // finishAsyncTask reached via answer()'s finishAsyncTask(turnId, result) once a QUESTION
+            // finishAsyncTask reached via answer()'s own finishAsyncTask(task, result) once a QUESTION
             // is resolved, completeExceptionally(t) just below when send() itself throws, or a CB-516
             // abandon() on teardown. Without this, MessageService.reply's rendezvous fast path (the
             // one an async ticket always takes) never told the push loop anything happened — see the
@@ -1079,7 +1131,22 @@ public final class MessageService {
                     finishAsyncTask(task, result);
                 }
             } catch (Throwable t) {
-                task.future.completeExceptionally(t);
+                // fleetd #329 (F2): finishAsyncTask above already completes task.future — on its very
+                // first line — before doing anything else, so anything that throws afterward (inside
+                // finishAsyncTask's own cleanup, or from a future addition to this try block) lands
+                // here with the future already resolved. completeExceptionally on an already-completed
+                // future is a silent no-op: it returns false and does nothing, so without the check
+                // below the exception simply vanished — no log, no metric, nothing. Measured (see the
+                // ticket): temporarily reintroducing the fleetd #324 NPE reproduced 19 real exceptions
+                // on the ordinary path, with 74/74 tests staying green and not one log line produced.
+                // Do not stop completing the future first — finishAsyncTask completing before it
+                // cleans up is what makes a late failure harmless to the ticket's own result — only
+                // add the missing visibility for the case where that step, or whatever ran after it,
+                // has already lost the race to report through the future.
+                if (!task.future.completeExceptionally(t)) {
+                    log.error("async send {} -> {} threw after its ticket was already resolved",
+                            ticket, target, t);
+                }
             }
         });
         pruneTerminalTickets();
@@ -1247,6 +1314,10 @@ public final class MessageService {
      */
     private void finishAsyncTask(Task task, Reply result) {
         task.future.complete(result);
+        if (afterFinishAsyncTaskCompleteHookForTest != null) {
+            // Test-only (fleetd #329, F2): see the field's own javadoc.
+            afterFinishAsyncTaskCompleteHookForTest.run();
+        }
         String turnId = task.turnId;
         if (turnId != null) {
             if (finishAsyncTaskRaceHook != null) {
@@ -1276,6 +1347,49 @@ public final class MessageService {
         this.finishAsyncTaskRaceHook = hook;
     }
 
+    /**
+     * Null in production; test seam for fleetd #329 (F2) — invoked from {@link #finishAsyncTask(Task,
+     * Reply)} unconditionally, immediately after {@code task.future.complete(result)} runs (before
+     * {@link Task#turnId} is even read, so it fires regardless of whether this task was ever asked).
+     * A test installs this to force an exception into exactly the shape fleetd #329 identified:
+     * something throws inside {@link #sendAsync}'s executor task after the async ticket's future is
+     * already resolved, so the surrounding {@code catch (Throwable t)} can only report failure through
+     * {@code completeExceptionally} — a silent no-op on an already-completed future. Engineering a
+     * real exception to land in that exact post-completion window is what the ticket itself had to do
+     * by temporarily deleting a production guard (fleetd #324's {@code turnId != null} check); this
+     * hook drives the identical shape deterministically instead.
+     */
+    private volatile Runnable afterFinishAsyncTaskCompleteHookForTest;
+
+    /**
+     * Test-only (fleetd #329, F2): install {@link #afterFinishAsyncTaskCompleteHookForTest}.
+     * Package-private so the test, in the same package, can reach it without widening any production
+     * API.
+     */
+    void setAfterFinishAsyncTaskCompleteHookForTest(Runnable hook) {
+        this.afterFinishAsyncTaskCompleteHookForTest = hook;
+    }
+
+    /**
+     * Null in production; test seam for fleetd #329 (F3) — invoked from {@link #reply} right after
+     * the single local read of {@code orphan.turnId} passes its null-check and before that (now-local)
+     * value is used as the {@code asyncTasksByTurn} removal key. Mirrors {@link
+     * #finishAsyncTaskRaceHook} exactly, for the structurally identical double-read fleetd #324 fixed
+     * in {@link #finishAsyncTask}: a test installs this to force, deterministically, {@code
+     * clearAsyncQuestion}'s unlocked {@code forgetTurn=true} path nulling {@link Task#turnId} in that
+     * exact window, and to confirm the single-read fix tolerates it (the captured local is used
+     * unconditionally, so a hook that nulls the field afterward cannot affect this call).
+     */
+    private volatile Runnable replyOrphanTurnIdRaceHookForTest;
+
+    /**
+     * Test-only (fleetd #329, F3): install {@link #replyOrphanTurnIdRaceHookForTest}. Package-private
+     * so the test, in the same package, can reach it without widening any production API.
+     */
+    void setReplyOrphanTurnIdRaceHookForTest(Runnable hook) {
+        this.replyOrphanTurnIdRaceHookForTest = hook;
+    }
+
     /**
      * Test-only (fleetd #324): run the exact production cleanup {@link #ask}'s own timeout path runs
      * unlocked — {@link #clearAsyncQuestion(String, boolean)} with {@code forgetTurn=true} — so a test
@@ -1285,14 +1399,6 @@ public final class MessageService {
         clearAsyncQuestion(turnId, true);
     }
 
-    /** Complete the async ticket correlated to a specific answered turn. */
-    private void finishAsyncTask(String turnId, Reply result) {
-        Task task = asyncTasksByTurn.get(turnId);
-        if (task != null) {
-            finishAsyncTask(task, result);
-        }
-    }
-
     /** A new send must not open a waiter while an async ticket owns this worker's paused turn. */
     private boolean hasAsyncQuestion(String target) {
         return asyncTasksByTurn.values().stream().anyMatch(task -> target.equals(task.target));

fleetd/src/test/java/dev/ltms/fleet/inject/InjectorTest.java

@@ -48,7 +48,7 @@ class InjectorTest {
 
     @Test
     void deliversWhenIdle() {
-        CompletableFuture<Void> f = injector.enqueue(T, "hello", TestTurnTokens.inert(T));
+        CompletableFuture<Void> f = injector.enqueue(T, "hello", TestTurnTokens.inert(T)).completion();
         assertFalse(f.isDone(), "not delivered until an injectable status arrives");
         injector.onStatus(T, AgentStatus.IDLE);
         assertTrue(f.isDone());
@@ -170,6 +170,32 @@ class InjectorTest {
         assertEquals(List.of("a", "b", "c"), sent());
     }
 
+    @Test
+    void cancellingTheMiddleDeliveryKeepsTheFollowingDeliveryReachable() {
+        Injector.Delivery first = injector.enqueue(T, "same text", TestTurnTokens.inert(T));
+        Injector.Delivery cancelled = injector.enqueue(T, "same text", TestTurnTokens.inert(T));
+        injector.enqueue(T, "after cancelled", TestTurnTokens.inert(T));
+
+        assertEquals(Injector.Cancellation.CANCELLED, injector.cancel(cancelled));
+        injector.onStatus(T, AgentStatus.IDLE);
+        injector.onStatus(T, AgentStatus.WORKING);
+        injector.onStatus(T, AgentStatus.IDLE);
+
+        assertEquals(List.of("same text", "after cancelled"), sent(),
+                "cancellation must match the exact Delivery and preserve the remaining FIFO queue");
+        assertTrue(first.completion().isDone());
+    }
+
+    @Test
+    void cancellationReportsDeliveredWhenPickupWonTheRace() {
+        Injector.Delivery delivery = injector.enqueue(T, "already sent", TestTurnTokens.inert(T));
+        injector.onStatus(T, AgentStatus.IDLE);
+
+        assertEquals(Injector.Cancellation.DELIVERED, injector.cancel(delivery),
+                "a cancellation after pickup must not claim that the text stayed queued");
+        assertEquals(List.of("already sent"), sent());
+    }
+
     @Test
     void activeWhileQueuedOrInFlightThenQuietAfterTurnCompletes() {
         assertTrue(injector.activeTargets().isEmpty());
@@ -378,7 +404,7 @@ class InjectorTest {
     void sendFailureDropsMessageAndFailsItsFuture() {
         FakeHerdr failing = new FakeHerdr().agentSendFailsWith("send_failed");
         Injector inj = new Injector(new AgentControl(failing));
-        CompletableFuture<Void> f = inj.enqueue(T, "boom", TestTurnTokens.inert(T));
+        CompletableFuture<Void> f = inj.enqueue(T, "boom", TestTurnTokens.inert(T)).completion();
 
         inj.onStatus(T, AgentStatus.IDLE);
         assertTrue(f.isCompletedExceptionally());
@@ -387,7 +413,7 @@ class InjectorTest {
 
     @Test
     void dropFailsPendingWaiters() {
-        CompletableFuture<Void> f = injector.enqueue(T, "orphan", TestTurnTokens.inert(T));
+        CompletableFuture<Void> f = injector.enqueue(T, "orphan", TestTurnTokens.inert(T)).completion();
         injector.drop(T, new HerdrException("worker gone", "pane_not_found", null));
         assertTrue(f.isCompletedExceptionally(), "queued waiters unblock when the worker vanishes");
     }
@@ -396,8 +422,8 @@ class InjectorTest {
     void dropPassesTheRealCauseForQueuedAndDeliveredWork() {
         Captor cap = new Captor();
         Injector inj = new Injector(new AgentControl(herdr), cap);
-        CompletableFuture<Void> delivered = inj.enqueue(T, "delivered", TestTurnTokens.inert(T));
-        CompletableFuture<Void> queued = inj.enqueue(T, "queued", TestTurnTokens.inert(T));
+        CompletableFuture<Void> delivered = inj.enqueue(T, "delivered", TestTurnTokens.inert(T)).completion();
+        CompletableFuture<Void> queued = inj.enqueue(T, "queued", TestTurnTokens.inert(T)).completion();
 
         inj.onStatus(T, AgentStatus.IDLE);    // deliver the first message
         inj.onStatus(T, AgentStatus.WORKING); // its turn is now in flight; one remains queued
@@ -449,7 +475,7 @@ class InjectorTest {
         Captor cap = new Captor();
         List<String> forgotten = new ArrayList<>();
         Injector inj = new Injector(new AgentControl(herdr), cap, _ -> false, forgotten::add);
-        CompletableFuture<Void> f = inj.enqueue(T, "task", TestTurnTokens.inert(T));
+        CompletableFuture<Void> f = inj.enqueue(T, "task", TestTurnTokens.inert(T)).completion();
 
         for (int i = 0; i < READINESS_SAMPLES; i++) inj.onStatus(T, AgentStatus.IDLE);
 
@@ -563,7 +589,7 @@ class InjectorTest {
         StatusPoller poller = new StatusPoller(new AgentControl(idle), inj, 10);
         poller.start();
         try {
-            CompletableFuture<Void> delivered = inj.enqueue(T, "via-poller", TestTurnTokens.inert(T));
+            CompletableFuture<Void> delivered = inj.enqueue(T, "via-poller", TestTurnTokens.inert(T)).completion();
             delivered.get(2, TimeUnit.SECONDS); // completes when the poller drives the send
         } finally {
             poller.stop();
@@ -582,7 +608,7 @@ class InjectorTest {
     void deliveredFutureCarriesSendFailure() {
         FakeHerdr failing = new FakeHerdr().agentSendFailsWith("send_failed");
         Injector inj = new Injector(new AgentControl(failing));
-        CompletableFuture<Void> f = inj.enqueue(T, "boom", TestTurnTokens.inert(T));
+        CompletableFuture<Void> f = inj.enqueue(T, "boom", TestTurnTokens.inert(T)).completion();
         inj.onStatus(T, AgentStatus.IDLE);
         ExecutionException ex = assertThrows(ExecutionException.class, f::get);
         assertInstanceOf(HerdrException.class, ex.getCause());

fleetd/src/test/java/dev/ltms/fleet/inject/StatusPollerRoutingTest.java

@@ -41,7 +41,7 @@ class StatusPollerRoutingTest {
         poller.start();
         try {
             CompletableFuture<Void> delivered =
-                    injector.enqueue(LEAD_TARGET, "via-poller", TestTurnTokens.inert(LEAD_TARGET));
+                    injector.enqueue(LEAD_TARGET, "via-poller", TestTurnTokens.inert(LEAD_TARGET)).completion();
             // Must resolve quickly: refining against the WRONG daemon (member) never classifies
             // out of UNKNOWN, so this would time out under the bug.
             delivered.get(2, TimeUnit.SECONDS);
@@ -65,7 +65,7 @@ class StatusPollerRoutingTest {
         poller.start();
         try {
             CompletableFuture<Void> delivered =
-                    injector.enqueue(LEAD_TARGET, "via-poller", TestTurnTokens.inert(LEAD_TARGET));
+                    injector.enqueue(LEAD_TARGET, "via-poller", TestTurnTokens.inert(LEAD_TARGET)).completion();
             assertThrows(TimeoutException.class, () -> delivered.get(500, TimeUnit.MILLISECONDS),
                     "a lead target must never be refined from the member daemon's pane content");
         } finally {

fleetd/src/test/java/dev/ltms/fleet/msg/MessageServiceTest.java

@@ -1,5 +1,9 @@
 package dev.ltms.fleet.msg;
 
+import ch.qos.logback.classic.Level;
+import ch.qos.logback.classic.Logger;
+import ch.qos.logback.classic.spi.ILoggingEvent;
+import ch.qos.logback.core.read.ListAppender;
 import dev.ltms.fleet.herdr.AgentControl;
 import dev.ltms.fleet.herdr.AgentStatus;
 import dev.ltms.fleet.herdr.FakeHerdr;
@@ -11,6 +15,7 @@ import dev.ltms.fleet.mcp.PrimaryRegistry;
 import dev.ltms.fleet.inject.Injector;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
+import org.slf4j.LoggerFactory;
 
 import java.util.concurrent.CompletableFuture;
 import java.util.concurrent.TimeUnit;
@@ -253,7 +258,7 @@ class MessageServiceTest {
         injector.onStatus(T, AgentStatus.IDLE);    // first delivery
         injector.onStatus(T, AgentStatus.WORKING); // first turn in flight
 
-        CompletableFuture<Void> queued = injector.enqueue(T, "second task", TestTurnTokens.inert(T));
+        CompletableFuture<Void> queued = injector.enqueue(T, "second task", TestTurnTokens.inert(T)).completion();
         CompletableFuture<Rendezvous.Resolution> waiter = rendezvous.currentWaiter(T);
         injector.drop(T, new HerdrException("agent target sol not found", "agent_not_found", null));
 
@@ -1041,6 +1046,105 @@ class MessageServiceTest {
                 "the reply completed its own ticket directly and never touched the inbox");
     }
 
+    /**
+     * fleetd #329 (F1). {@code answer()} completes the async ticket by looking {@code turnId} up in
+     * {@code asyncTasksByTurn} a SECOND time (the first is at :991, purely to re-register the
+     * {@code asyncTasksByWaiter} entry for #282's chained-ask case). That second lookup races
+     * {@code ask()}'s own unlocked timeout cleanup ({@code clearAsyncQuestion(turnId, true)}, run from
+     * {@code markAskTimedOut} + forgetting): {@code ask()}'s {@code ticket.answer().get(timeoutMillis)}
+     * can time out at essentially the same instant {@code answer()}'s {@code rendezvous.answerAsk}
+     * call above already succeeded and unblocked the worker. fleetd #324's single-read fix does not
+     * help here — that fixed a torn read of one already-held {@link MessageService} internal
+     * {@code Task}; this is a second, independent map lookup by a caller that no longer holds the
+     * {@code Task} it already found once.
+     *
+     * <p>This test does not wait for that real race to land on its own schedule — it drives the exact
+     * sequence the ticket describes (worker asks, primary answers, worker's real reply arrives) and
+     * fires the identical production cleanup {@code ask()}'s timeout path runs
+     * ({@code clearAsyncQuestion(turnId, true)}, via the {@code forgetTurnForTest} seam fleetd #324
+     * already merged) at the point between "the worker's own {@code ask()} call has unblocked" and
+     * "the worker's real {@code fleet_reply} arrives" — the exact window fleetd #329 names.
+     *
+     * <p>What this proves: given that exact interleaving, the async ticket must still resolve to the
+     * worker's real reply, not stay stuck {@link MessageService.Phase#PENDING} forever. What it does
+     * not prove: that the interleaving itself is reachable in production on its own timing — that is
+     * established by reading the code (see the ticket's "path in"), not by this test, for the same
+     * reason fleetd #324's own race test says so.
+     */
+    @Test
+    void aReplyRacingAsksTimeoutCleanupStillCompletesTheAsyncTicket() throws Exception {
+        String ticket = messages.sendAsync(T, "task that asks");
+        awaitWaiting();
+        injectDelivery();
+
+        CompletableFuture<MessageService.AskResult> ask =
+                CompletableFuture.supplyAsync(() -> messages.ask(T, "which config?", 5000));
+        MessageService.TaskView asking = awaitTicketPhase(ticket, MessageService.Phase.ASKING);
+        String turnId = asking.turnId();
+
+        CompletableFuture<MessageService.Reply> answer =
+                CompletableFuture.supplyAsync(() -> messages.answer(turnId, "config.yaml", 5000));
+        assertEquals("config.yaml", ask.get(5, TimeUnit.SECONDS).answer(),
+                "the worker's own ask() call must have already unblocked with the primary's answer "
+                        + "before we force the race below");
+
+        // ask()'s own unlocked timeout cleanup can forget this exact turnId at essentially the same
+        // instant answer() has already unblocked the worker and is now waiting on the resumed turn's
+        // real reply — reproduce that interleaving directly instead of trying to win a real race.
+        messages.forgetTurnForTest(turnId);
+
+        assertTrue(messages.reply(T, "PR opened: https://example/pulls/42"));
+
+        assertEquals(MessageService.Outcome.REPLIED, answer.get(5, TimeUnit.SECONDS).outcome(),
+                "the primary's own answer() call must still see the worker's real reply");
+        MessageService.TaskView done = awaitTicketPhase(ticket, MessageService.Phase.DONE);
+        assertEquals("PR opened: https://example/pulls/42", done.reply(),
+                "fleet_poll{ticket} must return the worker's real reply, not stay PENDING forever "
+                        + "just because ask()'s timeout cleanup forgot this turnId first");
+    }
+
+    /**
+     * fleetd #329 (F3). {@link MessageService#reply} reads the same orphan {@code Task}'s {@code
+     * turnId} twice on this path (once to check it is non-null, once as the {@code
+     * asyncTasksByTurn.remove} key) — the exact double-read shape fleetd #324 fixed in {@code
+     * finishAsyncTask}. This test drives the same real sequence as {@code
+     * aReplyAfterAnswerTimesOutStillCompletesTheAsyncTicket} (worker asks, primary answers, the
+     * primary's own bounded wait for the resumed turn expires) to reach a task with {@code turnId}
+     * genuinely stamped and no live rendezvous waiter open — the state {@code askAnsweredAsyncTasks}
+     * matches here — then fires the identical production cleanup {@code ask()}'s own timeout path
+     * runs ({@code clearAsyncQuestion(turnId, true)}, via the {@code forgetTurnForTest} seam fleetd
+     * #324 merged) at the point between the check and the removal use, via a dedicated test hook
+     * mirroring {@code finishAsyncTaskRaceHook}.
+     */
+    @Test
+    void replyToAnOrphanedTaskSurvivesTurnIdGoingNullBetweenItsTwoReads() throws Exception {
+        String ticket = messages.sendAsync(T, "task that asks");
+        awaitWaiting();
+        injectDelivery();
+
+        CompletableFuture<MessageService.AskResult> ask =
+                CompletableFuture.supplyAsync(() -> messages.ask(T, "which config?", 5000));
+        MessageService.TaskView asking = awaitTicketPhase(ticket, MessageService.Phase.ASKING);
+        String turnId = asking.turnId();
+
+        MessageService.Reply answerReply = messages.answer(turnId, "config.yaml", 150);
+        assertEquals("config.yaml", ask.get(5, TimeUnit.SECONDS).answer());
+        assertEquals(MessageService.Outcome.TIMED_OUT_WORKING, answerReply.outcome(),
+                "the primary's own bounded wait must give up first, leaving turnId stamped with no "
+                        + "live waiter — the state reply()'s F3 code path matches");
+
+        messages.setReplyOrphanTurnIdRaceHookForTest(() -> messages.forgetTurnForTest(turnId));
+        try {
+            assertTrue(messages.reply(T, "PR opened: https://example/pulls/42"));
+
+            MessageService.TaskView done = awaitTicketPhase(ticket, MessageService.Phase.DONE);
+            assertEquals("PR opened: https://example/pulls/42", done.reply(),
+                    "the ticket must still resolve to the worker's real reply despite the forced race");
+        } finally {
+            messages.setReplyOrphanTurnIdRaceHookForTest(null);
+        }
+    }
+
     /**
      * fleetd #307's ambiguity guard: an ask timeout frees its target ({@code hasAsyncQuestion}
      * becomes false the instant it lapses — proven above), so a second, independent delegation can
@@ -1151,6 +1255,63 @@ class MessageServiceTest {
         assertEquals("done", done.reply());
     }
 
+    // --- fleetd #329 (F2): an exception after the ticket's future completes must reach a log -----
+    //
+    // sendAsync's own executor task ends with catch (Throwable t) { task.future.completeExceptionally(t); }
+    // — but finishAsyncTask completes that same future on its first line, so anything that throws
+    // afterward hits an already-completed future: completeExceptionally returns false and does
+    // nothing, and (before this fix) nothing logged it either. Measured on the ticket: temporarily
+    // reintroducing the fleetd #324 NPE reproduced 19 real exceptions on the ordinary path with
+    // 74/74 tests staying green and zero log lines. There is no reachable production call site where
+    // finishAsyncTask throws after completing the future (fleetd #324 already closed the one that
+    // used to), so this test drives the shape directly via a dedicated test-only hook
+    // (afterFinishAsyncTaskCompleteHookForTest) rather than trying to engineer a real exception into
+    // that narrow window — the same technique fleetd #324's own race test and this ticket's F1/F3
+    // tests use for their own races.
+
+    private static ListAppender<ILoggingEvent> attachMessageServiceLog() {
+        Logger logger = (Logger) LoggerFactory.getLogger(MessageService.class);
+        ListAppender<ILoggingEvent> appender = new ListAppender<>();
+        appender.start();
+        logger.addAppender(appender);
+        return appender;
+    }
+
+    private static void detachMessageServiceLog(ListAppender<ILoggingEvent> appender) {
+        ((Logger) LoggerFactory.getLogger(MessageService.class)).detachAppender(appender);
+    }
+
+    @Test
+    void anExceptionAfterTheTicketFutureCompletesStillReachesTheLog() throws Exception {
+        ListAppender<ILoggingEvent> appender = attachMessageServiceLog();
+        try {
+            messages.setAfterFinishAsyncTaskCompleteHookForTest(() -> {
+                throw new RuntimeException("PROBE-329-F2");
+            });
+
+            String ticket = messages.sendAsync(T, "do the task");
+            awaitWaiting();
+            assertTrue(rendezvous.resolve(T, "done"));
+
+            // finishAsyncTask's own first line already completed the future with the real result
+            // BEFORE the hook threw — F2 is a visibility gap, not a correctness gap for the ticket
+            // itself, so the ticket's own outcome must be unaffected by the swallowed exception.
+            MessageService.TaskView done = awaitTicketPhase(ticket, MessageService.Phase.DONE);
+            assertEquals("done", done.reply());
+
+            assertTrue(appender.list.stream().anyMatch(e ->
+                            e.getLevel() == Level.ERROR
+                                    && e.getFormattedMessage().contains(ticket)
+                                    && e.getThrowableProxy() != null
+                                    && "PROBE-329-F2".equals(e.getThrowableProxy().getMessage())),
+                    "an exception thrown after the ticket's future already completed must still "
+                            + "reach the log, not vanish silently");
+        } finally {
+            messages.setAfterFinishAsyncTaskCompleteHookForTest(null);
+            detachMessageServiceLog(appender);
+        }
+    }
+
     // --- CB-582: fleet_status pendingAsk() ------------------------------------------------------
 
     @Test
@@ -1607,7 +1768,10 @@ class MessageServiceTest {
         assertEquals(MessageService.Outcome.TIMED_OUT_QUEUED, r.outcome());
 
         assertTrue(messages.hasQueuedDelivery(T),
-                "a TIMED_OUT_QUEUED send leaves the message still queued in the injector");
+                "a TIMED_OUT_QUEUED send still records the undelivered delivery for fleet health");
+        injector.onStatus(T, AgentStatus.IDLE);
+        assertTrue(herdr.calls.stream().noneMatch(c -> c.method().equals("agent.prompt")),
+                "a TIMED_OUT_QUEUED send must be cancelled, not delivered when the worker later goes idle");
     }
 
     @Test