#275: abandon() sweeps an ASKING ticket only on a definite teardown

Confirmed reachable: a target torn down for good (fleet_stop / the idle
reaper) while its async ticket sits in fleet_ask (Phase.ASKING) got
permanently stuck. resolveQuestion already closes the forward waiter, the
question == null guard excluded the task from abandon()'s sweep, and by the
time the worker's own fleet_ask lapses (~55-115s) the released session no
longer appears in FleetHealthMonitor's roster, so nothing ever calls
abandon() again. fleet_poll{ticket} then reports PENDING forever.

Add abandon(target, reason, sweepAsking) — sessions.onRelease (a definite
teardown: the pane is being stopped right now) passes true and now fails the
ASKING ticket and closes its reverse-rendezvous ask. FleetHealthMonitor's
health-classification call keeps the 2-arg overload (sweepAsking=false):
a GONE/NEVER_READY reading is a guess from the live agent list, not a
teardown it performed, and abandonDoesNotFailAnAsyncTicketWaitingForAnAnswer
already covers why an active ask must survive that guess (the primary may
be mid-answer for the same turn). hasOrphanedDelegation is left unchanged
for the same reason — it must not flag a live, active ask as orphaned.

Proven with a test driving the real public sequence (sendAsync -> ask ->
abandon(..., true)), not a hand-built task map; reverted the widening to
confirm it goes red, then restored it.

fleetd/src/main/java/dev/ltms/fleet/Fleetd.java

@@ -593,7 +593,11 @@ public final class Fleetd {
             if (detail.agentSessionId() != null) {
                 reason += " agentSessionId=" + detail.agentSessionId();
             }
-            messages.abandon(detail.terminalId(), reason);
+            // fleetd #275: this is an explicit teardown (fleet_stop, or the idle reaper) — the
+            // worker's pane is being stopped right now, so an open fleet_ask has no turn left to
+            // resume into. Sweep it too, unlike FleetHealthMonitor's health-classification call
+            // (see MessageService.abandon's javadoc for why those two must differ).
+            messages.abandon(detail.terminalId(), reason, true);
             replyInbox.release(detail.terminalId());
             primaryRegistry.forgetDelegation(detail.terminalId()); // CB-532: don't leak the lead binding
         });

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

@@ -360,6 +360,18 @@ public final class MessageService {
      * {@link #ask} clears the ticket's question and returns it to {@code PENDING}, but {@link #send}
      * already closed the forward waiter the instant the question surfaced, so the target has
      * neither an accepted nor a queued delivery left to show for it.
+     *
+     * <p><strong>Deliberately still {@code question == null} only (fleetd #275).</strong> This
+     * method must not also report a still-{@link Phase#ASKING} task as orphaned: the worker may
+     * genuinely be waiting on a live primary that is about to (or already mid-{@link #answer})
+     * answer it, and {@link dev.ltms.fleet.health.FleetHealthMonitor} would classify that as
+     * {@code DELEGATION_ORPHANED} on nothing more than an active, healthy conversation. {@link
+     * #abandon(String, String, boolean)}'s {@code sweepAsking} path fixes the actual reachable gap
+     * (a target torn down for good while genuinely {@code ASKING}) at the point of teardown itself,
+     * by completing the task's future right there — so by the time this method would ever see it,
+     * {@code task.future.isDone()} is already {@code true} and it is excluded regardless of this
+     * guard. Widening this check instead of that one would trade a real fix for false positives on
+     * every ordinary in-flight question.
      */
     public boolean hasOrphanedDelegation(String target) {
         if (target == null || hasAcceptedDelivery(target) || hasQueuedDelivery(target)) {
@@ -580,6 +592,39 @@ public final class MessageService {
      *         reply — see the note above)
      */
     public boolean abandon(String target, String reason) {
+        return abandon(target, reason, false);
+    }
+
+    /**
+     * As {@link #abandon(String, String)}, with control over whether a task still paused in
+     * {@code fleet_ask} ({@link Phase#ASKING}) is swept too (fleetd #275).
+     *
+     * <p>{@code sweepAsking} must be {@code true} only when the caller has independent, certain
+     * knowledge that {@code target} can never resume its turn — today that is only
+     * {@code sessions.onRelease}'s teardown (an explicit {@code fleet_stop}, or the idle reaper):
+     * the worker's pane is being stopped right now, so whatever it was mid-{@code fleet_ask} about
+     * has no turn left to resume into. {@link dev.ltms.fleet.health.FleetHealthMonitor}'s
+     * health-classification call keeps passing {@code false} (via {@link #abandon(String, String)}):
+     * a GONE/NEVER_READY reading is the daemon's best guess from the live agent list, not a teardown
+     * it performed itself, and {@code abandonDoesNotFailAnAsyncTicketWaitingForAnAnswer} documents
+     * why an active ask must survive that guess — the primary may already be mid-{@link #answer} for
+     * the very same turn, and completing it here first would preempt a real answer with a misleading
+     * failure.
+     *
+     * <p><strong>Without {@code sweepAsking} on the release path, a target torn down while
+     * genuinely {@code ASKING} was unrecoverable.</strong> {@link #resolveQuestion} had already
+     * closed the forward waiter the instant the question surfaced (so the {@code waiter} branch
+     * below finds nothing to fail), the {@code question == null} guard excluded the task from
+     * {@code matching} (so the loop below skipped it too), and the worker's own {@code fleet_ask}
+     * clears {@link Task#question} back to {@code null} only once it lapses (the reverse-rendezvous
+     * window — up to {@code FleetMcp.ASK_DEFAULT_TIMEOUT_MS} / {@code FleetApp.MAX_ASK_TIMEOUT_MS},
+     * 55–115s) — by which point the released session no longer appears in {@code sessions.roster()}
+     * for {@link dev.ltms.fleet.health.FleetHealthMonitor} to ever re-observe, so nothing was ever
+     * left to call {@link #abandon} on this target again. The ticket then sat in {@link #tasks}
+     * forever: not terminal, so {@link #pruneTerminalTickets} never dropped it, and
+     * {@code fleet_poll} reported it stuck at {@link Phase#PENDING} for good.
+     */
+    public boolean abandon(String target, String reason, boolean sweepAsking) {
         boolean hadStrandedReply = hasStrandedReply(target);
         // CB-640: the session is gone — nothing will ever accept or deliver into it now.
         strandedReplies.remove(target);
@@ -590,7 +635,8 @@ public final class MessageService {
 
         List<Task> matching = new ArrayList<>();
         for (Task task : tasks.values()) {
-            if (target.equals(task.target) && task.question == null && !task.future.isDone()) {
+            if (target.equals(task.target) && (sweepAsking || task.question == null)
+                    && !task.future.isDone()) {
                 matching.add(task);
             }
         }
@@ -607,11 +653,20 @@ public final class MessageService {
         for (Task task : matching) {
             boolean isRecovery = task == recoveryTask && recovered != null;
             Reply outcome = isRecovery ? recovered : new Reply(Outcome.WORKER_FAILED, reason);
+            String turnId = task.turnId;
             if (task.future.complete(outcome)) {
                 if (outcome.outcome() == Outcome.WORKER_FAILED) {
                     asyncFailed = true;
-                } else if (task.turnId != null) {
-                    asyncTasksByTurn.remove(task.turnId, task);
+                }
+                if (turnId != null) {
+                    // #275: whether this task was swept out of ASKING or was already answered and
+                    // only waiting on its resumed turn's real reply (#137), nothing will ever
+                    // complete this turnId now — drop it from this class's own bookkeeping AND the
+                    // reverse-rendezvous itself, so hasAsyncQuestion(target) stops reporting a turn
+                    // that is actually done, and a late answer() sees it as lapsed rather than
+                    // resolving a question nothing is listening for any more.
+                    asyncTasksByTurn.remove(turnId, task);
+                    rendezvous.closeAsk(turnId);
                 }
             } else if (isRecovery) {
                 // The recovered reply was already drained out of the inbox, but this task resolved

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

@@ -828,6 +828,56 @@ class MessageServiceTest {
         assertEquals(MessageService.Outcome.REPLIED, answer.get(5, TimeUnit.SECONDS).outcome());
     }
 
+    // --- fleetd #275: a target torn down FOR GOOD while genuinely ASKING must not orphan --------
+    //
+    // sessions.onRelease (fleet_stop, or the idle reaper) is the one abandon() caller that knows
+    // for certain the target can never resume: its pane is being stopped right now. Unlike the
+    // health-classification caller above (a GONE/NEVER_READY guess, not a teardown it performed),
+    // it must sweep an ASKING ticket right here — see MessageService.abandon(String, String,
+    // boolean)'s javadoc for the full reachability chain this closes: without this, the forward
+    // waiter is already closed by the time the question surfaces, the ASKING guard skips the task,
+    // and by the time the worker's own fleet_ask lapses (~55-115s later) the released session no
+    // longer appears in FleetHealthMonitor's roster for anything to ever sweep it again — leaving
+    // fleet_poll{ticket} stuck PENDING forever.
+
+    @Test
+    void abandonWithSweepAskingFailsATornDownTargetsAskingTicket() throws Exception {
+        String ticket = messages.sendAsync(T, "task that asks");
+        awaitWaiting();
+        injectDelivery();
+
+        CompletableFuture<MessageService.AskResult> ask =
+                CompletableFuture.supplyAsync(() -> messages.ask(T, "which config?", 300));
+        MessageService.TaskView asking = awaitTicketPhase(ticket, MessageService.Phase.ASKING);
+
+        assertTrue(messages.abandon(T, "the worker session was released before it replied", true),
+                "a released target's open ask can never resume, so it must fail right here");
+
+        MessageService.TaskView failed = awaitTicketPhase(ticket, MessageService.Phase.FAILED);
+        assertEquals("the worker session was released before it replied", failed.detail());
+
+        // The reverse-rendezvous ask is torn down too: the worker's still-blocked fleet_ask rides
+        // out its own timeout (nothing completed its answer future), and a late answer() for the
+        // same turnId must see it as lapsed rather than resolving a question nobody is waiting on.
+        assertEquals(MessageService.AskOutcome.TIMED_OUT, ask.get(5, TimeUnit.SECONDS).outcome());
+        assertEquals(MessageService.Outcome.STALE_TURN,
+                messages.answer(asking.turnId(), "config.yaml", 200).outcome());
+    }
+
+    @Test
+    void abandonWithoutSweepAskingBehavesLikeTheTwoArgOverload() throws Exception {
+        String ticket = messages.sendAsync(T, "task that asks");
+        awaitWaiting();
+        injectDelivery();
+
+        CompletableFuture.supplyAsync(() -> messages.ask(T, "which config?", 5000));
+        awaitTicketPhase(ticket, MessageService.Phase.ASKING);
+
+        assertFalse(messages.abandon(T, "agent target term_a not found", false),
+                "sweepAsking=false must match the plain abandon(target, reason) overload");
+        assertEquals(MessageService.Phase.ASKING, messages.poll(ticket).phase());
+    }
+
     // --- #137: a fleet_ask round-trip must not orphan the ticket's own reply -------------------
     //
     // The primary's fleet_send{turnId} answer call is itself bounded (a real MCP call, capped well