#317: refuse an unresolved caller instead of promoting it to primary

ConnectionIdentity.resolve() called pids.pidForLocalPort(remotePort),
which returns -1 both on a real failure and (silently, no log line)
when lsof just finds no matching process. terminalForPid(-1) then
matches no pane, so CallerResolver's loopback-trust fallback could not
tell that caller apart from a genuine primary and handed it
Principal.primary(...) — granting SPAWN, STOP, SEND and DRAIN to a
worker whose PID lookup failed. This is the escalation PaneLocator's
own javadoc already names; CB-161's ancestry walk only helps once a
candidate pid exists, and a failed lookup has none.

Fix: ConnectionIdentity.Caller gets a resolved() predicate (pid > 0),
centralised next to the -1 sentinel it tests for the same reason
isLoopback() is centralised (fleetd #305: two independent copies of
one rule already drifted once). CallerResolver's loopback-trust
fallback now requires c.resolved() before granting PRIMARY; an
unresolved caller gets Principal.anonymous() — the same already-tested
"authenticated as nothing" outcome used everywhere else in that
method, so the refusal is a clean, named, unsurprising result rather
than something that looks like a bug.

Also logs the previously-silent "lsof ran clean, found no match" case
in LsofPeerPidLookup at DEBUG, since that (not a slow lsof — the
waitFor result was already discarded) is the likelier real trigger.

loopbackTrustTreatsANonWorkerLoopbackCallerAsThePrimary is untouched
and still green: a real pid that owns no pane (the actual primary) is
still resolved() and still PRIMARY. Token mode is unaffected — it
never consults c.pid() at all.

Mutation-tested: reverting only the CallerResolver.java guard
reproduces the escalation exactly (aFailedPeerPidLookupIsRefusedNotPromotedToPrimary
fails with "expected: <ANONYMOUS> but was: <PRIMARY>").

fleetd/src/main/java/dev/ltms/fleet/auth/CallerResolver.java

@@ -236,7 +236,15 @@ public final class CallerResolver {
         // loopback-trust: same-host callers that are not workers are the primary. A non-loopback
         // caller is anonymous even here — and startup refuses that combination anyway
         // (FleetConfig.validateAuthExposure), so this is defence in depth, not the control.
-        return isLoopback(remoteAddr) ? Principal.primary(c.pid()) : Principal.anonymous();
+        //
+        // fleetd #317: "not a worker" must not be conflated with "identity unresolved". The real
+        // primary is a real process — its pid resolves (c.resolved()), it just owns no herdr pane.
+        // A caller whose peer-PID lookup failed (LsofPeerPidLookup's -1 sentinel — on any failure,
+        // silently including "lsof found no match") has no such pid, and PaneLocator's own javadoc
+        // already names what happens if that case is handed the primary role: a worker→primary
+        // escalation. So an unresolved caller is refused (ANONYMOUS — the same clean, already-tested
+        // "authenticated as nothing" outcome used everywhere else in this method), never promoted.
+        return isLoopback(remoteAddr) && c.resolved() ? Principal.primary(c.pid()) : Principal.anonymous();
     }
 
     private boolean presentedTokenMatches(String authorizationHeader) {
@@ -262,11 +270,15 @@ public final class CallerResolver {
         return token.isEmpty() ? null : token;
     }
 
+    /**
+     * fleetd #305: delegates to {@link ConnectionIdentity#isLoopback}. This used to be a second,
+     * independent copy of the same rule, and the two drifted: this one accepted all of
+     * {@code 127.0.0.0/8}, {@code ConnectionIdentity}'s accepted only {@code 127.0.0.1}. A caller
+     * from {@code 127.0.0.2} therefore had its identity skipped (so it had no terminal) and was
+     * then read as loopback here — which under loopback-trust is the primary. Sharing the inputs
+     * would not have prevented that; only sharing the computation does.
+     */
     private static boolean isLoopback(String remoteAddr) {
-        if (remoteAddr == null) {
-            return false;
-        }
-        return remoteAddr.equals("127.0.0.1") || remoteAddr.equals("::1")
-                || remoteAddr.equals("0:0:0:0:0:0:0:1") || remoteAddr.startsWith("127.");
+        return ConnectionIdentity.isLoopback(remoteAddr);
     }
 }

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

@@ -157,6 +157,7 @@ public final class Injector {
         boolean awaitingCompletion; // a delivered message's turn is not yet known-complete
         boolean turnObserved;      // saw a real `working` sample since that delivery (turn ran)
         int unknownSinceTurn;      // consecutive `unknown` samples while a delegation is outstanding (CB-109)
+        int unknownSincePostTurn;  // the same, for the post-turn housekeeping phase (fleetd #306)
         int notReadySincePoll;     // consecutive injectable samples a queued message waited on the readiness gate (CB-114)
         boolean postTurnPending;   // completion observed; adapter housekeeping has not started yet
         boolean awaitingPostTurnPickup;
@@ -217,10 +218,12 @@ public final class Injector {
                 t.awaitingPickup = false;
                 t.injectableSincePickup = 0;
                 t.unknownSinceTurn = 0;
+                t.unknownSincePostTurn = 0;
                 t.notReadySincePoll = 0;
                 if (t.awaitingCompletion) t.turnObserved = true;
             } else if (status.injectable()) { // IDLE or BLOCKED
                 t.unknownSinceTurn = 0;
+                t.unknownSincePostTurn = 0;
                 if (t.awaitingPostTurnPickup) {
                     if (++t.injectableSincePostTurnPickup >= PICKUP_GRACE_POLLS) {
                         t.awaitingPostTurnPickup = false;
@@ -315,6 +318,24 @@ public final class Injector {
                     t.unknownSinceTurn = 0;
                     turnFailed = true;
                 }
+                // fleetd #306: the same escape for the post-turn housekeeping phase. Four latches
+                // gate delivery (awaitingCompletion, postTurnPending, awaitingPostTurnPickup,
+                // postTurnObserved) and only the first had a way out of a sustained unknown streak —
+                // a gate that closed one direction only. The other two below are released here as
+                // well; postTurnPending needs no escape because it is cleared unconditionally on the
+                // line after the listener call that sets it.
+                //
+                // This does NOT set turnFailed. The delegated turn already completed and its waiter
+                // already resolved — what is outstanding is adapter housekeeping (the `/clear`).
+                // Reporting a turn failure here would drive SessionManager.onFailed on a session
+                // that genuinely finished its work, which is a worse lie than the wedge.
+                if ((t.awaitingPostTurnPickup || t.postTurnObserved)
+                        && ++t.unknownSincePostTurn >= TURN_STALL_GRACE_POLLS) {
+                    t.awaitingPostTurnPickup = false;
+                    t.postTurnObserved = false;
+                    t.injectableSincePostTurnPickup = 0;
+                    t.unknownSincePostTurn = 0;
+                }
             }
 
             // Reclaim the entry once the worker is fully quiescent (nothing queued, no pickup or

fleetd/src/main/java/dev/ltms/fleet/mcp/ConnectionIdentity.java

@@ -36,6 +36,25 @@ public final class ConnectionIdentity {
      * primary / an off-host client) and its {@code pid} (or {@code -1} if not resolvable).
      */
     public record Caller(String terminal, long pid) {
+
+        /**
+         * Whether the OS peer-PID lookup actually succeeded — {@code false} means {@code pid} is
+         * the {@code -1} sentinel, not a real process id, so this caller's identity could not be
+         * established at all. That is a different fact from a real pid that simply owns no worker
+         * pane (the primary's own connection): the primary is {@code resolved()} and has a
+         * {@code null terminal}; an unresolvable caller is {@code !resolved()} and also has a
+         * {@code null terminal}. The two look identical through {@link #terminal} alone, which is
+         * exactly how fleetd #317 happened — a failed {@code lsof} lookup and a genuine primary both
+         * fell through to {@code Principal.primary(...)}.
+         *
+         * <p>Centralised here, next to the sentinel it tests, for the same reason
+         * {@link ConnectionIdentity#isLoopback} is centralised rather than left for each caller to
+         * reimplement: a raw {@code pid > 0} check duplicated at every call site is precisely the
+         * "one rule, two copies" shape that let #305 drift.
+         */
+        public boolean resolved() {
+            return pid > 0;
+        }
     }
 
     /** Resolve the caller's terminal and PID from one peer-PID lookup. */
@@ -60,7 +79,30 @@ public final class ConnectionIdentity {
         return pid > 0 ? cwds.cwdForPid(pid) : null;
     }
 
-    private static boolean isLoopback(String addr) {
-        return "127.0.0.1".equals(addr) || "::1".equals(addr) || "0:0:0:0:0:0:0:1".equals(addr);
+    /**
+     * Whether {@code addr} is a same-host address, and therefore one whose peer PID is worth
+     * looking up. <strong>This is the one definition of loopback in the daemon</strong> —
+     * {@code CallerResolver} calls it rather than keeping its own, because the two used to differ
+     * and that difference was a privilege escalation (fleetd #305).
+     *
+     * <p>The whole of {@code 127.0.0.0/8} counts, not just {@code 127.0.0.1}. On Linux every
+     * address in that range is bound to {@code lo} by default, so a process can connect to
+     * {@code 127.0.0.1:8765} with a source address of {@code 127.0.0.2} — measured on the Linux
+     * fleet host, where binding that source succeeds.
+     *
+     * <p><strong>Being strict here does not make the daemon safer; it makes it unsafe.</strong>
+     * That reads backwards, so it is worth stating plainly. This predicate does not decide whether
+     * a caller is trusted — it decides whether the caller's identity is <em>resolved at all</em>.
+     * Returning false means {@link #resolve} answers "no terminal", and downstream a caller with no
+     * terminal is treated as the primary under loopback-trust. So every address excluded here is an
+     * address on which a worker silently becomes the lead. Widening a check normally weakens it;
+     * widening this one is what closes the hole.
+     */
+    public static boolean isLoopback(String addr) {
+        if (addr == null) {
+            return false;
+        }
+        String a = addr.startsWith("::ffff:") ? addr.substring(7) : addr; // IPv4-mapped IPv6
+        return a.startsWith("127.") || "::1".equals(a) || "0:0:0:0:0:0:0:1".equals(a);
     }
 }

fleetd/src/main/java/dev/ltms/fleet/mcp/FleetMcp.java

@@ -22,6 +22,7 @@ import dev.ltms.fleet.placement.BackendQuarantine;
 import dev.ltms.fleet.placement.PlacementException;
 import dev.ltms.fleet.session.SessionManager;
 import dev.ltms.fleet.session.MemberSession;
+import dev.ltms.fleet.session.ShuttingDownException;
 import dev.ltms.fleet.session.WorktreeRequest;
 import dev.ltms.fleet.peer.MemberRole;
 import dev.ltms.fleet.peer.PeerLauncher;
@@ -813,7 +814,12 @@ public final class FleetMcp {
             return error("fleet_reply is for workers only — could not identify the calling worker "
                     + "from the connection");
         }
-        if (content == null) {
+        // fleetd #302: isBlank, not == null, to match fleet_send's own guard above. MessageService
+        // .reply now REJECTS blank content, and this handler is a bare BiFunction with no try/catch
+        // around it — so a whitespace-only fleet_reply would leave here as an uncaught
+        // IllegalArgumentException instead of this clean tool error. Null and whitespace are the
+        // same mistake by the caller and must get the same answer.
+        if (isBlank(content)) {
             return error("content is required");
         }
         messages.reply(callerTerminal, content);
@@ -957,6 +963,10 @@ public final class FleetMcp {
             return text(json(memberView(member)));
         } catch (GuardException e) {
             return error("subscription boundary: " + e.getMessage());
+        } catch (ShuttingDownException e) {
+            // fleetd #308: the daemon's shutdown drain has already started — refuse loudly rather
+            // than register a session drainAll will never see again.
+            return error("shutting down: " + e.getMessage());
         } catch (PlacementException e) {
             // CB-599: no candidate had capacity (maxLoad, quarantine, or all-exhausted) — distinct
             // from "profile does not exist" below.

fleetd/src/main/java/dev/ltms/fleet/mcp/LsofPeerPidLookup.java

@@ -41,6 +41,14 @@ public final class LsofPeerPidLookup implements PeerPidLookup {
             if (!p.waitFor(2, TimeUnit.SECONDS)) {
                 p.destroyForcibly();
             }
+            if (found < 0) {
+                // fleetd #317: this is the silent path — lsof ran clean and simply reported no
+                // matching process (e.g. queried before the OS socket table settles). Previously
+                // this logged nothing at all, which is exactly why the escalation went unnoticed;
+                // the exception path below already logs. A caller now refused because of this is
+                // still refused (never promoted) — this line only makes the refusal diagnosable.
+                log.debug("lsof peer-pid lookup for port {} found no matching process", port);
+            }
             return found;
         } catch (Exception e) {
             log.debug("lsof peer-pid lookup for port {} failed: {}", port, e.getMessage());

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

@@ -187,6 +187,24 @@ public final class MessageService {
         private volatile Long completedNanos;
         private volatile Reply question;
         private volatile String turnId;
+        /**
+         * Set when this task's {@code fleet_ask} lapsed with no answer (fleetd #307):
+         * {@link #clearAsyncQuestion} then forgets {@link #turnId} (nulls it and drops the task from
+         * {@code asyncTasksByTurn}) so {@link #hasAsyncQuestion} stops reporting the target BUSY — a
+         * later {@code fleet_send} to it must be accepted, not refused. But the worker's turn is
+         * still genuinely live: it resumed on its own and will eventually call its real
+         * {@code fleet_reply}. Losing {@link #turnId} loses {@link #askAnsweredAsyncTasks}' only
+         * signal that such a reply belongs to this task, so that reply used to fall straight to the
+         * inbox and strand — {@code fleet_poll} stayed {@code PENDING} forever, later force-failed by
+         * {@link #abandon} with the misleading "session released before it replied". This flag is a
+         * second, independent signal that survives the forgetting: {@link #askAnsweredAsyncTasks}
+         * accepts it in place of a live {@link #turnId}, without ever re-adding the task to
+         * {@code asyncTasksByTurn} (so the BUSY release is untouched). Cleared implicitly once
+         * {@link #future} resolves — every match in {@link #askAnsweredAsyncTasks} already requires
+         * {@code !future.isDone()}, so a task that recovered (or was later failed by
+         * {@link #abandon}) can never match again regardless of this flag's value.
+         */
+        private volatile boolean askTimedOut;
 
         private Task(String ticket, String target, LongSupplier nowNanos) {
             this.ticket = ticket;
@@ -395,18 +413,16 @@ public final class MessageService {
      * {@link Rendezvous#resolveQuestion} must keep today's {@code NO_WAITER} behaviour — questions
      * are interactive and must never be queued.
      *
-     * <p><strong>Ambiguous match also falls to the inbox.</strong> {@link #askAnsweredAsyncTasks}
-     * cannot actually return more than one entry today (see its own javadoc for why — in short,
-     * {@link #hasAsyncQuestion} keeps a target BUSY, so no second task can reach this state, for as
-     * long as an earlier one's {@code turnId} is still stamped). That is an emergent guarantee from
-     * two other facts, not one this method enforces, so this branch stays in as defence in depth
-     * rather than being removed as dead code: if it ever weakens, returning whichever candidate a
-     * {@code ConcurrentHashMap} iteration reaches first would let a genuine reply complete the
-     * <em>wrong</em> ticket — silently handing the lead something that reads like a correct answer to
-     * a delegation the worker never touched, which is worse than a failure because the lead acts on
-     * it. When more than one candidate exists, guessing is not safe: fall back to the inbox exactly
-     * as the zero-candidate case does, and let {@link #abandon} apply the eventual recovery
-     * deterministically instead.
+     * <p><strong>Ambiguous match also falls to the inbox.</strong> {@link #askAnsweredAsyncTasks} can
+     * return more than one entry — a reachable state, not a hypothetical one (see its own javadoc:
+     * an {@code fleet_ask} that lapsed with no answer, fleetd #307, frees the target for a completely fresh
+     * delegation, which can itself go on to ask-and-lapse before the first worker's real reply
+     * arrives). Returning whichever candidate a {@code ConcurrentHashMap} iteration reaches first
+     * would let a genuine reply complete the <em>wrong</em> ticket — silently handing the lead
+     * something that reads like a correct answer to a delegation the worker never touched, which is
+     * worse than a failure because the lead acts on it. When more than one candidate exists, guessing
+     * is not safe: fall back to the inbox exactly as the zero-candidate case does, and let
+     * {@link #abandon} apply the eventual recovery deterministically instead.
      *
      * <p><strong>{@code content} is required (fleetd #302).</strong> Both doors that reach this
      * method must reject a missing/blank reply the same way, so the check lives here rather than in
@@ -434,15 +450,18 @@ public final class MessageService {
             count(FleetMetrics.REPLIES, "path", "rendezvous");
             return true;                       // a live send took it — unchanged fast path
         }
-        // #137: no live rendezvous waiter, but this may be the worker's real fleet_reply resuming a
-        // turn that {@link #answer} already gave up waiting on. answer()'s own bounded wait (the
-        // primary's fleet_send{turnId} call, capped well under a minute) can time out and close its
-        // waiter long before the worker — now actually resuming real work — finishes and replies. That
-        // reply used to have nowhere to land but the session inbox, leaving the async ticket's future
-        // unresolved forever: fleet_poll{ticket} stayed PENDING until fleet_stop's abandon() forced it
-        // FAILED with a misleading "session released before it replied" reason, even though the reply
-        // had, in fact, arrived. Completing the matching ticket directly here means fleet_poll{ticket}
-        // sees the real reply instead.
+        // #137/fleetd #307: no live rendezvous waiter, but this may be the worker's real fleet_reply resuming
+        // a turn that either answer() (#137) or ask() (fleetd #307) already gave up waiting on:
+        //  - answer()'s own bounded wait (the primary's fleet_send{turnId} call, capped well under a
+        //    minute) can time out and close its waiter long before the worker — now actually resuming
+        //    real work — finishes and replies.
+        //  - ask()'s own wait for the primary can time out first, with the worker resuming on its own
+        //    and finishing unanswered.
+        // Either way that reply used to have nowhere to land but the session inbox, leaving the async
+        // ticket's future unresolved forever: fleet_poll{ticket} stayed PENDING until fleet_stop's
+        // abandon() forced it FAILED with a misleading "session released before it replied" reason,
+        // even though the reply had, in fact, arrived. Completing the matching ticket directly here
+        // means fleet_poll{ticket} sees the real reply instead.
         List<Task> candidates = askAnsweredAsyncTasks(session);
         if (candidates.size() == 1) {
             Task orphan = candidates.get(0);
@@ -473,34 +492,42 @@ public final class MessageService {
     }
 
     /**
-     * Every still-open async task on {@code target} whose {@code fleet_ask} was already answered —
-     * its {@link Task#turnId} is stamped but its {@link Task#question} was cleared by {@link #answer}
-     * — yet whose future is not resolved yet (#137). Empty if no such task exists, including the
-     * common case where {@code target}'s worker never used {@code fleet_ask} at all (a task that was
-     * never asked has {@code turnId == null}, so it can never match here and only ever completes
-     * through the ordinary rendezvous fast path in {@link #reply}).
+     * Every still-open async task on {@code target} whose worker is genuinely expected to send a
+     * real {@code fleet_reply} next with nothing left registered to catch it: either its
+     * {@code fleet_ask} was already answered — {@link Task#turnId} is stamped but {@link
+     * Task#question} was cleared by {@link #answer} — or its {@code fleet_ask} lapsed unanswered and
+     * {@link Task#askTimedOut} marks that (fleetd #307; {@link Task#turnId} is {@code null} by then, forgotten
+     * so the target is not left BUSY — see {@link Task#askTimedOut}'s own javadoc). Either way the
+     * task's future is not resolved yet. Empty if no such task exists, including the common case
+     * where {@code target}'s worker never used {@code fleet_ask} at all (a task that was never asked
+     * has both {@code turnId == null} and {@code askTimedOut == false}, so it can never match here and
+     * only ever completes through the ordinary rendezvous fast path in {@link #reply}).
      *
-     * <p><strong>Returns at most one entry today — verified, not assumed.</strong> {@link #send}
-     * refuses to open a waiter on {@code target} while {@link #hasAsyncQuestion} is true, and that
-     * check matches ANY task whose {@code turnId} is still stamped in {@code asyncTasksByTurn} —
-     * not only while its question is still open. {@link #answer} deliberately leaves that stamp in
-     * place ({@code clearAsyncQuestion(turnId, false)}) until the resumed turn's own future actually
-     * resolves, at which point {@link #finishAsyncTask} both removes the stamp AND completes that
-     * task's future in the same call. So a second task can never reach "{@code turnId} stamped, future
-     * still open" — the exact pair this method matches on — while a first one already holds it: by
-     * the time the stamp is gone, so is the eligibility. This is an emergent property of those two
-     * facts holding together, not something this method (or its callers) enforces on its own — flip
-     * {@code forgetTurn} to {@code true} in that one {@link #answer} call and it silently stops being
-     * true, with nothing left to fail loudly. The callers below still handle "more than one" as
-     * defence in depth against exactly that, not because they exercise it today: {@link #reply}
-     * treats it as unresolvable and falls back to the inbox; {@link #abandon} would pick the oldest
-     * deterministically (its own {@code matching} list has no such guarantee — see its javadoc).
+     * <p><strong>Can return more than one entry — reachable, not just defence in depth.</strong>
+     * {@link #send} refuses to open a waiter on {@code target} while {@link #hasAsyncQuestion} is
+     * true, and that check matches ANY task whose {@code turnId} is still stamped in
+     * {@code asyncTasksByTurn}. While a task's {@code turnId} stays stamped — {@link #answer} leaves
+     * it in place ({@code clearAsyncQuestion(turnId, false)}) until {@link #finishAsyncTask} removes
+     * the stamp and completes the future in the same call — no second task on the same target can
+     * reach an eligible state, because {@link #send} would refuse it as BUSY first. That single-task
+     * guarantee holds only for the {@code turnId}-stamped half of this method's match: an
+     * {@link Task#askTimedOut} task is, by construction, no longer stamped in {@code asyncTasksByTurn}
+     * (that is the whole point of forgetting {@code turnId} in {@link #clearAsyncQuestion}), so the
+     * target is free the moment one ask lapses. A fresh, independent {@code sendAsync} to the same
+     * target can then be dispatched, itself pause on {@code fleet_ask}, and itself time out — landing
+     * a second {@code askTimedOut} task on the very target the first one is still waiting to answer
+     * for. Two (or more) genuinely open tasks on one target is therefore a real, reachable state
+     * today, not a hypothetical: {@link #reply} treats it as unresolvable and falls back to the
+     * inbox rather than guess which task a reply belongs to (guessing wrong would hand the lead a
+     * plausible-looking answer to a delegation the worker never touched — worse than a failure,
+     * because the lead acts on it); {@link #abandon} instead picks the oldest deterministically (its
+     * own {@code matching} list has a different, wider match — see its javadoc).
      */
     private List<Task> askAnsweredAsyncTasks(String target) {
         List<Task> candidates = new ArrayList<>();
         for (Task task : tasks.values()) {
-            if (target.equals(task.target) && task.question == null && task.turnId != null
-                    && !task.future.isDone()) {
+            if (target.equals(task.target) && task.question == null && !task.future.isDone()
+                    && (task.turnId != null || task.askTimedOut)) {
                 candidates.add(task);
             }
         }
@@ -898,6 +925,12 @@ public final class MessageService {
             return new AskResult(AskOutcome.ANSWERED, answer);
         } catch (TimeoutException e) {
             log.debug("fleet_ask from {} went unanswered in {}ms", workerSession, timeoutMillis);
+            // fleetd #307: mark the task BEFORE clearAsyncQuestion(forgetTurn=true) below drops it out of
+            // asyncTasksByTurn and nulls its turnId — that forgetting is deliberate and stays (it is
+            // what keeps the target from staying BUSY forever), but it would otherwise also erase
+            // askAnsweredAsyncTasks' only signal that the worker's eventual real fleet_reply still
+            // belongs to this task, stranding it in the inbox with a false "never replied" verdict.
+            markAskTimedOut(ticket.turnId());
             clearAsyncQuestion(ticket.turnId(), true);
             return new AskResult(AskOutcome.TIMED_OUT, null);
         } catch (ExecutionException e) {
@@ -1162,6 +1195,23 @@ public final class MessageService {
         return task;
     }
 
+    /**
+     * Mark {@code turnId}'s task as having a {@code fleet_ask} that lapsed with no answer (fleetd #307), so
+     * {@link #askAnsweredAsyncTasks} still recognizes the worker's eventual real {@code fleet_reply}
+     * as belonging to it after {@link #clearAsyncQuestion}'s {@code forgetTurn=true} erases
+     * {@link Task#turnId} — see {@link Task#askTimedOut}. Must be called before that forgetting, while
+     * {@code turnId} can still resolve the task in {@code asyncTasksByTurn}; a lookup afterward would
+     * find nothing. Only when it matches the task's current turn — same guard as
+     * {@link #clearAsyncQuestion} — so a chained second {@code fleet_ask} (#282) that already moved
+     * the task to a fresh {@code turnId} cannot mark it for a turn that is no longer its own.
+     */
+    private void markAskTimedOut(String turnId) {
+        Task task = asyncTasksByTurn.get(turnId);
+        if (task != null && turnId.equals(task.turnId)) {
+            task.askTimedOut = true;
+        }
+    }
+
     /** Clear an answered or lapsed question, but only when it matches the ticket's current turn. */
     private void clearAsyncQuestion(String turnId, boolean forgetTurn) {
         // CB-582: tell the push loop first — like ticketCollected, a removal for a turnId it never

fleetd/src/main/java/dev/ltms/fleet/rest/FleetApp.java

@@ -19,6 +19,7 @@ import dev.ltms.fleet.peer.PeerUnreachableException;
 import dev.ltms.fleet.placement.PlacementException;
 import dev.ltms.fleet.msg.MessageService;
 import dev.ltms.fleet.session.SessionManager;
+import dev.ltms.fleet.session.ShuttingDownException;
 import dev.ltms.fleet.peer.MemberRole;
 import dev.ltms.fleet.session.MemberSession;
 import dev.ltms.fleet.session.WorktreeRequest;
@@ -501,6 +502,11 @@ public final class FleetApp {
             ctx.status(201).json(view(member));
         } catch (GuardException e) {
             ctx.status(403).json(Map.of("error", "subscription_boundary", "detail", e.getMessage()));
+        } catch (ShuttingDownException e) {
+            // fleetd #308: the daemon's shutdown drain has already started — 503, not a bare 500,
+            // so this reads the same as PlacementException below: valid request, refused because
+            // of a transient daemon state rather than a bad argument.
+            ctx.status(503).json(Map.of("error", "shutting_down", "detail", e.getMessage()));
         } catch (PlacementException e) {
             // CB-599: no candidate had capacity (maxLoad, quarantine, or all-exhausted) — a benign,
             // likely-transient refusal, distinct from "profile does not exist" below. 503: the
@@ -510,6 +516,12 @@ public final class FleetApp {
             ctx.status(400).json(Map.of("error", "unknown_profile", "detail", e.getMessage()));
         } catch (PeerUnreachableException e) {
             ctx.status(502).json(Map.of("error", "spawn_timeout", "detail", e.getMessage()));
+        } catch (HerdrException e) {
+            // fleetd #304: not every herdr failure on the spawn path is a readiness timeout, so
+            // PeerUnreachableException above does not cover this. Without this catch the exception
+            // escapes to Javalin's default 500, while fleet_spawn reports the same failure as a
+            // clean named error (FleetMcp.spawn) — the #297 one-door-guarded shape.
+            herdrError(ctx, e);
         }
     }
 
@@ -530,13 +542,29 @@ public final class FleetApp {
         return (s == null || s.isBlank()) ? null : s;
     }
 
-    /** Tear a worker down by pane id. */
+    /**
+     * Tear a worker down by pane id.
+     *
+     * <p>fleetd #304: the {@code HerdrException} catch is not cosmetic. {@code release} deregisters
+     * the session, notifies the release listener and preserves a dirty worktree <em>before</em> it
+     * calls {@code launcher.stop}, so a throw from that stop arrives after the teardown the caller
+     * asked for has already happened. Letting it escape gave Javalin's default 500, which tells the
+     * caller to retry — and the retry finds nothing in the registry, reaches the same stop, and
+     * throws again, so it can never succeed. {@code herdrError} instead answers 404 ("the pane is
+     * gone, stop retrying") or 502 ("herdr is upstream and broken, a retry may help"), matching what
+     * {@code fleet_stop} reports for the same failure.
+     */
     private void stopMember(Context ctx) {
         String paneId = ctx.pathParam("paneId");
         if (!allow(ctx, routeAction("DELETE /members/{paneId}"), paneId)) {
             return;
         }
-        sessions.release(paneId);
+        try {
+            sessions.release(paneId);
+        } catch (HerdrException e) {
+            herdrError(ctx, e);
+            return;
+        }
         ctx.status(204);
     }
 

fleetd/src/main/java/dev/ltms/fleet/session/GitWorktrees.java

@@ -93,6 +93,9 @@ public final class GitWorktrees implements Worktrees {
     /** OS group name for {@link #shareWithGroup} (fleetd #185 stage 3); {@code null} ⇒ feature off. */
     private final String group;
     private final Consumer<String> afterWorktreeAdded;
+    /** How the initial {@code git worktree add} command runs. Package-private test seam for an
+     *  interrupted command after Git has made worktree state. */
+    private final Function<String[], String> worktreeAddRunner;
     /** How {@link #shareWithGroup}'s processes (git config / chgrp / chmod / find) actually run.
      *  Defaults to the real {@link #exec(String...)}. Package-private test seam so a unit test can
      *  prove "no group configured ⇒ zero processes spawned" and inspect exactly what a configured
@@ -132,7 +135,13 @@ public final class GitWorktrees implements Worktrees {
 
     /** Test seam combining a configurable {@code group} with {@link #afterWorktreeAdded}. */
     GitWorktrees(String configuredRoot, String group, Consumer<String> afterWorktreeAdded) {
-        this(configuredRoot, group, afterWorktreeAdded, null);
+        this(configuredRoot, group, afterWorktreeAdded, null, null);
+    }
+
+    /** Test seam for changing how {@link #shareWithGroup}'s processes run. */
+    GitWorktrees(String configuredRoot, String group, Consumer<String> afterWorktreeAdded,
+                  Function<String[], String> shareGroupRunner) {
+        this(configuredRoot, group, afterWorktreeAdded, shareGroupRunner, null);
     }
 
     /**
@@ -141,13 +150,15 @@ public final class GitWorktrees implements Worktrees {
      * exactly what commands a configured group runs, without a real second OS user/group.
      *
      * @param shareGroupRunner {@code null} ⇒ the real {@link #exec(String...)}.
+     * @param worktreeAddRunner {@code null} ⇒ the real {@link #exec(String...)}.
      */
     GitWorktrees(String configuredRoot, String group, Consumer<String> afterWorktreeAdded,
-                 Function<String[], String> shareGroupRunner) {
+                  Function<String[], String> shareGroupRunner, Function<String[], String> worktreeAddRunner) {
         this.configuredRoot = configuredRoot;
         this.group = (group == null || group.isBlank()) ? null : group;
         this.afterWorktreeAdded = afterWorktreeAdded == null ? _ -> {} : afterWorktreeAdded;
         this.shareGroupRunner = shareGroupRunner != null ? shareGroupRunner : this::exec;
+        this.worktreeAddRunner = worktreeAddRunner != null ? worktreeAddRunner : this::exec;
     }
 
     @Override
@@ -166,8 +177,8 @@ public final class GitWorktrees implements Worktrees {
         String wt = path.toAbsolutePath().toString();
         log.info("adding worktree branch={} path={} base={}", branch, wt, base);
         removeUserInfoFromHttpsOrigin(repoRoot);
-        exec("git", "-C", repoRoot, "worktree", "add", wt, "-b", branch, base);
         try {
+            worktreeAddRunner.apply(new String[] {"git", "-C", repoRoot, "worktree", "add", wt, "-b", branch, base});
             afterWorktreeAdded.accept(wt);
             requireCredentialFreeHttpsOrigin(wt);
             configureEnvironmentCredentialHelper(repoRoot, wt);
@@ -181,10 +192,11 @@ public final class GitWorktrees implements Worktrees {
     }
 
     /**
-     * {@code add()} has already created the worktree and its branch by the time any step from
-     * {@link #afterWorktreeAdded} through {@link #isolateToolSurface} can throw — including
+     * {@code git worktree add} may have created the worktree and its branch by the time it, or any
+     * later step through {@link #isolateToolSurface}, throws. This includes
      * {@link #requireCredentialFreeHttpsOrigin}, an intended security refusal, not only an IO
-     * accident. Without this, {@code add()} never returns, so its caller
+     * accident. A Git-reported {@code worktree add} failure usually creates nothing, but an
+     * interrupted command can leave partial state. Without cleanup, {@code add()} never returns, so its caller
      * ({@code SessionManager#acquireWithWorktree}) never receives a path to register or clean up:
      * its local {@code path} stays null, the {@code if (path != null)} guard in its own catch block
      * never runs, and the worktree directory and branch leak on disk forever with nothing tracking
@@ -204,6 +216,10 @@ public final class GitWorktrees implements Worktrees {
      * used in {@code SessionManager#acquireWithWorktree}'s own catch block.
      */
     private void cleanupAfterAddFailure(String repoRoot, String worktreePath, String branch, RuntimeException original) {
+        if (!Files.exists(Path.of(worktreePath))) {
+            log.debug("provisioning failed before worktree {} existed; nothing to clean up", worktreePath);
+            return;
+        }
         log.warn("provisioning failed for branch={} path={}: {} — cleaning up before rethrowing",
                 branch, worktreePath, original.getMessage());
         try {

fleetd/src/main/java/dev/ltms/fleet/session/SessionManager.java

@@ -21,6 +21,7 @@ import java.util.Optional;
 import java.util.Set;
 import java.util.concurrent.ConcurrentHashMap;
 import java.util.concurrent.TimeUnit;
+import java.util.concurrent.atomic.AtomicBoolean;
 import java.util.concurrent.atomic.AtomicLong;
 import java.util.function.Consumer;
 import java.util.function.LongSupplier;
@@ -61,6 +62,8 @@ public final class SessionManager implements TurnListener {
     private final LongSupplier nowNanos;
     private final int contextCap;
     private final boolean clearAfterTurn;
+    /** Null in production; test seam for the interval before an idle session's conditional release. */
+    private final Consumer<MemberSession> beforeIdleRelease;
     private volatile MemberLifecycle memberLifecycle = MemberLifecycle.NONE;
     /**
      * CB-586: the repo root the fleet actually works in, remembered the first time a worktree
@@ -71,6 +74,16 @@ public final class SessionManager implements TurnListener {
      */
     private volatile String fleetRepoRoot;
 
+    /**
+     * fleetd #308: flips true the instant {@link #drainAll} starts, before its registry snapshot
+     * is even taken — so a spawn already in flight sees the refusal as early as a plain flag can
+     * make it. This alone cannot close the race completely: a caller that read {@code false} just
+     * before the flip can still land in the registry after the snapshot. {@link #drainAll}'s
+     * post-loop sweep is what catches that straggler; the two mechanisms are deliberately paired,
+     * see {@link #drainAll}'s javadoc.
+     */
+    private final AtomicBoolean draining = new AtomicBoolean(false);
+
     /** CB-520: notified with a terminalId on every acquire; no-op until wired. */
     private final List<Consumer<String>> acquireListeners = new java.util.concurrent.CopyOnWriteArrayList<>();
     /** CB-516: notified with a {@link ReleaseDetail} on every release; no-op until wired. */
@@ -102,13 +115,23 @@ public final class SessionManager implements TurnListener {
     }
 
     public SessionManager(PeerLauncher launcher, Worktrees worktrees, LongSupplier nowNanos,
-                          int contextCap, boolean clearAfterTurn) {
+                           int contextCap, boolean clearAfterTurn) {
+        this(launcher, worktrees, nowNanos, contextCap, clearAfterTurn, null);
+    }
+
+    /**
+     * Package-private constructor for a deterministic reap/delivery race test. Production callers
+     * use the constructor above, whose null hook adds no callback or lock to an ordinary reap.
+     */
+    SessionManager(PeerLauncher launcher, Worktrees worktrees, LongSupplier nowNanos,
+                   int contextCap, boolean clearAfterTurn, Consumer<MemberSession> beforeIdleRelease) {
         this.launcher = launcher;
         this.worktrees = worktrees;
         this.presence = new PresenceFleet(this);
         this.nowNanos = nowNanos;
         this.contextCap = contextCap;
         this.clearAfterTurn = clearAfterTurn;
+        this.beforeIdleRelease = beforeIdleRelease;
     }
 
     /**
@@ -181,6 +204,14 @@ public final class SessionManager implements TurnListener {
     public MemberSession acquire(String profile, MemberRole role, String requestedCwd, String callerCwd,
                                  String ownerTerminal, WorktreeRequest wt,
                                  String sessionName, String resumeSessionId) {
+        // fleetd #308: refuse before anything else runs — no slot reservation, no launcher spawn —
+        // so a caller learns the daemon is going down instead of getting a session drainAll will
+        // never see again. Checked here because every other acquire(...) overload delegates to
+        // this one, so this is the single point every spawn path passes through.
+        if (draining.get()) {
+            throw new ShuttingDownException("fleetd is shutting down; refusing to spawn a session "
+                    + "the shutdown drain would never see");
+        }
         MemberRole memberRole = (role == null) ? MemberRole.DEV : role;
         requireResumeCapability(profile, resumeSessionId);
         // CB-619 / fleetd #123: an explicit profile bypasses placement (CompositePeerLauncher only
@@ -272,10 +303,32 @@ public final class SessionManager implements TurnListener {
      */
     private void release(String paneId, ReleaseCause cause) {
         MemberSession removed = registry.remove(paneId);
+        releaseRemoved(paneId, removed, handles.remove(paneId), cause);
+    }
+
+    /**
+     * Tear a session down only while {@code expected} is still its registry value. A lifecycle
+     * transition replaces the immutable record, so this prevents a reap based on an old READY or
+     * DONE record from stopping a worker that delivery has made BUSY.
+     */
+    private boolean releaseIfCurrent(MemberSession expected, ReleaseCause cause) {
+        if (!registry.remove(expected.paneId(), expected)) {
+            // A lifecycle transition replaced the record between the caller's check and this remove.
+            // Log it: this race is by definition unobservable otherwise, and a reaper that silently
+            // declines to reap is the hardest kind of behaviour to diagnose after the fact.
+            log.debug("skipping reap of pane={}: its registry record changed after the idle check "
+                    + "(most likely a delivery made it BUSY)", expected.paneId());
+            return false;
+        }
+        releaseRemoved(expected.paneId(), expected, handles.remove(expected.paneId()), cause);
+        return true;
+    }
+
+    private void releaseRemoved(String paneId, MemberSession removed, PeerHandle removedHandle,
+                                ReleaseCause cause) {
         // fleetd #209: remove right alongside the registry entry so a released session's handle is
         // never leaked — but keep the local reference below, so the id can still be resolved for
         // the ReleaseDetail this teardown notifies with.
-        PeerHandle removedHandle = handles.remove(paneId);
         boolean preserveWorktree = cause == ReleaseCause.SHUTDOWN;
         String snapshotRef = null;
         if (removed != null) {
@@ -846,14 +899,18 @@ public final class SessionManager implements TurnListener {
             }
             long idleNanos = now - s.lastActivityAtNanos();
             if (idleNanos > idleTtlNanos) {
-                log.debug("reaping idle session terminal={} pane={}: idle {}s exceeds the {}s ttl",
-                        s.terminalId(), s.paneId(), TimeUnit.NANOSECONDS.toSeconds(idleNanos),
-                        TimeUnit.NANOSECONDS.toSeconds(idleTtlNanos));
                 // CB-581: one session that fails to release must not abort the whole reaping pass —
                 // match drainAll's per-session try/catch so the rest of the roster still gets reaped.
                 try {
-                    release(s.paneId());
-                    reaped++;
+                    if (beforeIdleRelease != null) {
+                        beforeIdleRelease.accept(s);
+                    }
+                    if (releaseIfCurrent(s, ReleaseCause.COMPLETED)) {
+                        log.debug("reaping idle session terminal={} pane={}: idle {}s exceeds the {}s ttl",
+                                s.terminalId(), s.paneId(), TimeUnit.NANOSECONDS.toSeconds(idleNanos),
+                                TimeUnit.NANOSECONDS.toSeconds(idleTtlNanos));
+                        reaped++;
+                    }
                 } catch (RuntimeException e) {
                     log.warn("reap failed for pane={} terminal={} worktree={}; continuing with "
                             + "remaining sessions", s.paneId(), s.terminalId(), s.worktree(), e);
@@ -884,10 +941,40 @@ public final class SessionManager implements TurnListener {
      * a reason to delete a worker's only copy of its uncommitted work. A session still {@code BUSY}
      * when the timeout expired is abandoned mid-turn and logged loudly so an operator can find its
      * kept worktree.
+     *
+     * <p>fleetd #308: {@code roster()} is a one-shot snapshot (see its javadoc), and nothing used
+     * to stop a new session from registering after it was taken — {@link #acquire} stayed open for
+     * as long as this drain waited on a {@code BUSY} session, up to the whole {@code timeoutNanos}
+     * budget. Two things close that window, deliberately paired because neither alone is complete:
+     * {@link #draining} is flipped true before the snapshot is even taken, so {@link #acquire}
+     * refuses (invariant 3: loudly, via {@link ShuttingDownException}) as much of the window as a
+     * plain flag can close; and the sweep below re-reads the registry once the initial snapshot has
+     * fully drained and drains whatever a straggler — a caller that read the flag as {@code false}
+     * a moment before it flipped — still managed to register. The sweep shares the same
+     * {@code deadline} rather than getting its own: {@code timeoutNanos} is a budget for the WHOLE
+     * drain (see above), and a straggler must not buy the drain more time than the flag it lost the
+     * race against would have. In the ordinary case the sweep finds nothing and costs one empty
+     * {@link #roster()} call.
      */
     void drainAll(long timeoutNanos) {
         long deadline = System.nanoTime() + timeoutNanos;
-        for (MemberSession s : roster()) {
+        draining.set(true);
+        drainSnapshot(roster(), deadline);
+        List<MemberSession> stragglers = roster();
+        if (!stragglers.isEmpty()) {
+            log.warn("drain sweep found {} session(s) registered after the drain snapshot was "
+                    + "taken (raced past the shutdown guard); draining them too", stragglers.size());
+            drainSnapshot(stragglers, deadline);
+        }
+    }
+
+    /**
+     * Drain exactly the sessions in {@code snapshot}, waiting out a {@code BUSY} one against the
+     * shared whole-drain {@code deadline} before releasing it. Shared by {@link #drainAll}'s main
+     * pass and its post-loop straggler sweep (fleetd #308) so both honor the same one budget.
+     */
+    private void drainSnapshot(List<MemberSession> snapshot, long deadline) {
+        for (MemberSession s : snapshot) {
             try {
                 if (s.state() == MemberSession.State.BUSY) {
                     while (System.nanoTime() < deadline) {

fleetd/src/main/java/dev/ltms/fleet/session/ShuttingDownException.java

@@ -0,0 +1,18 @@
+package dev.ltms.fleet.session;
+
+/**
+ * Thrown by {@link SessionManager#acquire} when a spawn is requested after the daemon's shutdown
+ * drain has already begun (fleetd #308).
+ *
+ * <p>{@link SessionManager#drainAll} snapshots the registry once and tears down exactly what is
+ * in that snapshot. A session registered after the snapshot is invisible to the drain loop: its
+ * pane is left running and its worktree is never preserved, and nothing else ever reclaims
+ * either — the daemon's in-memory registry dies with the process. Refusing the spawn here,
+ * loudly, is what stops that session from ever being created in the first place, rather than
+ * silently handing the caller a session the daemon can no longer manage.
+ */
+public final class ShuttingDownException extends RuntimeException {
+    public ShuttingDownException(String message) {
+        super(message);
+    }
+}

fleetd/src/test/java/dev/ltms/fleet/auth/CallerResolverTest.java

@@ -103,6 +103,54 @@ class CallerResolverTest {
         assertEquals(Role.PRIMARY, p.role(), "the historical behaviour, now an explicit choice");
     }
 
+    // ── fleetd #317: an unresolvable caller must never be promoted to the primary ──────────────────
+    // #305 closed the trigger where a resolved pid matched no pane *and* had no ancestry walk to
+    // save it. This is the other trigger PaneLocator's javadoc names: the pid never resolves at
+    // all — LsofPeerPidLookup returns -1 on any failure, including (silently) "lsof found no
+    // match" — so there is no candidate pid for an ancestry walk to even attempt.
+
+    /**
+     * The failing-without-the-fix case. Before #317's fix, {@code c.terminal() == null} was the
+     * only test in the loopback-trust fallback, and an unresolved pid produces exactly that same
+     * {@code null} terminal as a genuine primary — so this caller was handed
+     * {@code Principal.primary(...)}, a real worker's failed lookup becoming indistinguishable from
+     * the lead.
+     */
+    @Test
+    void aFailedPeerPidLookupIsRefusedNotPromotedToPrimary() {
+        ConnectionIdentity unresolved = new ConnectionIdentity(new PaneLocator(herdr), _ -> -1);
+        Principal p = new CallerResolver(unresolved).resolve("127.0.0.1", 55555, null);
+
+        assertEquals(Role.ANONYMOUS, p.role(),
+                "an unresolvable caller must never be silently promoted to the primary");
+    }
+
+    /**
+     * The companion invariant #317 must not break: a caller whose lookup genuinely succeeded, and
+     * who simply owns no herdr pane — the real primary's own connection — is still the primary.
+     * This is {@link #loopbackTrustTreatsANonWorkerLoopbackCallerAsThePrimary} pinned again here,
+     * named for #317 and placed next to the test it must be distinguished from: same {@code null}
+     * terminal, opposite verdict, because {@code Caller.resolved()} tells them apart.
+     */
+    @Test
+    void aRealPidThatOwnsNoPaneIsStillThePrimaryNotRefused() {
+        Principal p = new CallerResolver(nonWorkerIdentity()).resolve("127.0.0.1", 55555, null);
+
+        assertEquals(Role.PRIMARY, p.role());
+    }
+
+    /** #317 point 4: token mode never consults {@code c.pid()}, so a failed lookup must not change it. */
+    @Test
+    void tokenModeIsUndisturbedByAnUnresolvedLookup() {
+        ConnectionIdentity unresolved = new ConnectionIdentity(new PaneLocator(herdr), _ -> -1);
+        CallerResolver r = new CallerResolver(unresolved, true, "s3cret");
+
+        assertEquals(Role.ANONYMOUS, r.resolve("127.0.0.1", 55555, null).role(),
+                "no credential is still just ANONYMOUS, as before #317 — unchanged by the lookup failing");
+        assertEquals(Role.PRIMARY, r.resolve("127.0.0.1", 55555, "Bearer s3cret").role(),
+                "a valid token still authenticates the primary even though the peer-pid lookup failed");
+    }
+
     @Test
     void tokenModeRefusesANonWorkerCallerThatPresentsNoToken() {
         Principal p = new CallerResolver(nonWorkerIdentity(), true, "s3cret")
@@ -413,4 +461,29 @@ class CallerResolverTest {
         assertThrows(IllegalArgumentException.class, () -> new CallerResolver(id, true, null));
         assertThrows(IllegalArgumentException.class, () -> new CallerResolver(id, true, "  "));
     }
+    @Test
+    void aWorkerOnAnyLoopbackSourceAddressIsStillAWorkerNotThePrimary() {
+        // fleetd #305: the escalation. ConnectionIdentity used to accept only 127.0.0.1, so a
+        // worker connecting from 127.0.0.2 resolved to no terminal, and this resolver's own
+        // (wider) loopback check then made it the PRIMARY — granting spawn, stop, send and drain.
+        // Measured on the Linux fleet host: binding a source of 127.0.0.2 succeeds there, so the
+        // path is real and not theoretical.
+        CallerResolver r = new CallerResolver(workerIdentity(), false, null);
+        for (String src : new String[]{"127.0.0.1", "127.0.0.2", "127.1.2.3", "::ffff:127.0.0.2"}) {
+            Principal p = r.resolve(src, 55555, null);
+            assertEquals(Role.WORKER, p.role(), "a worker must stay a worker from source " + src);
+            assertEquals("term_a", p.terminal(), "worker terminal from source " + src);
+        }
+    }
+
+    @Test
+    void aNonWorkerOnAnyLoopbackSourceAddressIsStillThePrimary() {
+        // The other direction of the same fix: widening the identity check must not demote a
+        // legitimate same-host primary that happens to connect from another 127.* address.
+        CallerResolver r = new CallerResolver(nonWorkerIdentity(), false, null);
+        for (String src : new String[]{"127.0.0.1", "127.0.0.2", "::ffff:127.0.0.1"}) {
+            assertEquals(Role.PRIMARY, r.resolve(src, 55555, null).role(), "source " + src);
+        }
+    }
+
 }

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

@@ -297,6 +297,68 @@ class InjectorTest {
         assertTrue(inj.activeTargets().isEmpty(), "the wedged target is reclaimed, not polled forever");
     }
 
+    /** A listener whose post-turn housekeeping always starts, as SessionManager's does with clearAfterTurn on. */
+    private static final class PostTurnListener implements TurnListener {
+        @Override public void onTurnComplete(String target) { }
+        @Override public boolean hasPostTurnAction(String target) { return true; }
+        @Override public boolean onTurnCompleteWithPostAction(String target) { return true; }
+    }
+
+    @Test
+    void aWorkerThatWedgesInUnknownAwaitingPostTurnPickupIsReleased() {
+        // fleetd #306: the post-turn phase had no way out of a sustained unknown streak, so the
+        // pickup latch stayed set, the target was polled forever, and every later message to it was
+        // blocked by the delivery gate — while the session still looked healthy.
+        Captor cap = new Captor();
+        Injector inj = new Injector(new AgentControl(herdr), new PostTurnListener());
+        inj.enqueue(T, "task", TestTurnTokens.inert(T));
+
+        inj.onStatus(T, AgentStatus.IDLE);    // deliver
+        inj.onStatus(T, AgentStatus.WORKING); // turn starts
+        inj.onStatus(T, AgentStatus.IDLE);    // turn completes; housekeeping dispatched
+        for (int i = 0; i < STALL_SAMPLES; i++) inj.onStatus(T, AgentStatus.UNKNOWN); // then wedges
+
+        assertTrue(inj.activeTargets().isEmpty(),
+                "a target wedged awaiting post-turn pickup must be reclaimed, not polled forever");
+        assertEquals(List.of(), cap.failed,
+                "the delegated turn already completed — a stuck /clear must not be reported as a failed turn");
+    }
+
+    @Test
+    void aWorkerThatWedgesInUnknownAfterPickingUpTheResetIsReleased() {
+        // The sibling latch. postTurnObserved is set when the reset is seen picked up (WORKING) and
+        // is cleared only on a later injectable sample, so a wedge right after pickup sticks too.
+        Captor cap = new Captor();
+        Injector inj = new Injector(new AgentControl(herdr), new PostTurnListener());
+        inj.enqueue(T, "task", TestTurnTokens.inert(T));
+
+        inj.onStatus(T, AgentStatus.IDLE);
+        inj.onStatus(T, AgentStatus.WORKING);
+        inj.onStatus(T, AgentStatus.IDLE);    // turn complete; reset dispatched
+        inj.onStatus(T, AgentStatus.WORKING); // reset picked up -> postTurnObserved
+        for (int i = 0; i < STALL_SAMPLES; i++) inj.onStatus(T, AgentStatus.UNKNOWN);
+
+        assertTrue(inj.activeTargets().isEmpty(), "a wedge after reset pickup must also be reclaimed");
+        assertEquals(List.of(), cap.failed, "still not a turn failure");
+    }
+
+    @Test
+    void aBriefUnknownDuringPostTurnHousekeepingDoesNotDropTheLatch() {
+        // The other direction: the escape must not fire on a glitch, or the queued next delegation
+        // would overtake housekeeping that is still running.
+        Injector inj = new Injector(new AgentControl(herdr), new PostTurnListener());
+        inj.enqueue(T, "first", TestTurnTokens.inert(T));
+        inj.enqueue(T, "second", TestTurnTokens.inert(T));
+
+        inj.onStatus(T, AgentStatus.IDLE);
+        inj.onStatus(T, AgentStatus.WORKING);
+        inj.onStatus(T, AgentStatus.IDLE);    // first completes; reset dispatched
+        for (int i = 0; i < 10; i++) inj.onStatus(T, AgentStatus.UNKNOWN); // well under the grace
+
+        assertFalse(inj.activeTargets().isEmpty(), "a brief glitch must not release the post-turn latch");
+        assertEquals(List.of("first"), sent(), "the queued delegation must not overtake housekeeping");
+    }
+
     @Test
     void aTransientUnknownGlitchNeitherFailsNorBlocksCompletion() {
         Captor cap = new Captor();

fleetd/src/test/java/dev/ltms/fleet/mcp/ConnectionIdentityTest.java

@@ -20,6 +20,17 @@ class ConnectionIdentityTest {
         assertEquals("term_a", with(_ -> FakeHerdr.WORKER_PID).callerTerminal("127.0.0.1", 55555));
     }
 
+    @Test
+    void resolvesWorkerFromAnyLoopbackSourceAddressNotJust127001() {
+        // fleetd #305. On Linux the whole 127.0.0.0/8 is bound to lo, so a worker can connect with
+        // a source address of 127.0.0.2. If identity resolution skips that address the caller has
+        // no terminal, and a caller with no terminal is the primary under loopback-trust — so this
+        // must resolve the worker, not null.
+        assertEquals("term_a", with(_ -> FakeHerdr.WORKER_PID).callerTerminal("127.0.0.2", 55555));
+        assertEquals("term_a", with(_ -> FakeHerdr.WORKER_PID).callerTerminal("127.1.2.3", 55555));
+        assertEquals("term_a", with(_ -> FakeHerdr.WORKER_PID).callerTerminal("::ffff:127.0.0.2", 55555));
+    }
+
     @Test
     void nullForOffHostCaller() {
         // A non-loopback peer can't be an on-host worker → treat as primary/unknown.
@@ -32,6 +43,22 @@ class ConnectionIdentityTest {
         assertNull(with(_ -> 999_999).callerTerminal("127.0.0.1", 55555));
     }
 
+    @Test
+    void callerIsUnresolvedWhenThePeerPidLookupFails() {
+        // fleetd #317: LsofPeerPidLookup returns -1 on any failure — a fork error, or (silently)
+        // simply no matching lsof line. Caller.resolved() is the one place that sentinel is tested.
+        ConnectionIdentity.Caller c = with(_ -> -1).resolve("127.0.0.1", 55555);
+        assertFalse(c.resolved(), "a -1 pid means the lookup failed, not that this pid owns no pane");
+    }
+
+    @Test
+    void callerIsResolvedWhenThePidIsRealEvenThoughItOwnsNoPane() {
+        // The primary's own connection: a real, lsof-found pid that just isn't a worker pane. This
+        // must read as "resolved" — the distinction #317 turns on.
+        ConnectionIdentity.Caller c = with(_ -> 999_999).resolve("127.0.0.1", 55555);
+        assertTrue(c.resolved());
+    }
+
     @Test
     void resolvesTheCallersPidAndCwd() {
         // CB-112: the primary maps to no pane, but its PID and cwd are still readable.

fleetd/src/test/java/dev/ltms/fleet/mcp/FleetMcpTest.java

@@ -189,7 +189,7 @@ class FleetMcpTest {
     }
 
     @Test
-    void unansweredAsyncAskReturnsTheTicketToPending() throws Exception {
+    void unansweredAsyncAskReturnsTheTicketToPendingThenAWorkersLateReplyStillCompletesIt() throws Exception {
         McpSchema.CallToolResult accepted = FleetMcp.sendAsync(messages, "term_a", "do it", null, Set.of());
         String ticket = textOf(accepted).substring(textOf(accepted).indexOf("ticket=") + "ticket=".length()).trim();
 
@@ -203,8 +203,15 @@ class FleetMcpTest {
         assertTrue(textOf(ask).contains("no answer"), textOf(ask));
         assertTrue(textOf(FleetMcp.poll(messages, ticket, null)).startsWith("[pending"));
 
+        // fleetd #307: the worker resumed on its own after the primary never answered, and its real
+        // fleet_reply must complete its OWN async ticket — not strand in the inbox with
+        // fleet_poll{ticket} stuck PENDING forever and later force-failed with a false "session
+        // released before it replied" reason. This used to land in the inbox instead (see the old
+        // assertion this replaced: messages.drainReplies("term_a").getFirst()...) — that was the bug.
         FleetMcp.reply(messages, "term_a", "finished after timeout");
-        assertEquals("finished after timeout", messages.drainReplies("term_a").getFirst().content());
+        assertEquals("finished after timeout", textOf(FleetMcp.poll(messages, ticket, null)));
+        assertTrue(messages.drainReplies("term_a").isEmpty(),
+                "the reply completed its own ticket directly and never touched the inbox");
     }
 
     @Test
@@ -326,6 +333,26 @@ class FleetMcpTest {
         assertEquals("orphan", drained.getFirst().content());
     }
 
+    @Test
+    void replyWithBlankContentIsACleanToolErrorNotAnUncaughtException() {
+        // fleetd #302: MessageService.reply now REJECTS blank content by throwing. fleet_reply's
+        // handler is a bare BiFunction with no try/catch around it, so if this guard only checked
+        // `== null` (as it did), a whitespace-only reply would leave the handler as an uncaught
+        // IllegalArgumentException instead of a tool error the caller can read. Null and whitespace
+        // are the same caller mistake and must get the same answer — the sibling fleet_send guard
+        // has always used isBlank for exactly this reason.
+        for (String blank : new String[] {null, "", "   ", "\n\t"}) {
+            McpSchema.CallToolResult res = assertDoesNotThrow(
+                    () -> FleetMcp.reply(messages, "term_a", blank),
+                    "blank content must be refused as a tool error, never thrown out of the handler");
+            assertEquals(Boolean.TRUE, res.isError(), "blank content is an error result");
+            assertTrue(textOf(res).contains("content is required"),
+                    "the error names the missing argument: " + textOf(res));
+        }
+        assertEquals(0, messages.drainReplies("term_a").size(),
+                "a refused reply must not reach the inbox");
+    }
+
     @Test
     void bridgePollWithTargetDrainsReplies() {
         // A reply with no open send queues it in the inbox.

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

@@ -957,6 +957,76 @@ class MessageServiceTest {
         assertEquals(MessageService.Phase.DONE, awaitTicketPhase(next, MessageService.Phase.DONE).phase());
     }
 
+    /**
+     * fleetd #307: a worker's {@code fleet_ask} can time out because the primary never answers —
+     * distinct from {@link #aReplyAfterAnswerTimesOutStillCompletesTheAsyncTicket}, where the
+     * primary DID answer and only its own bounded wait for the resumed turn expired.
+     * {@code ask()}'s timeout path deliberately forgets the task's {@code turnId} (so
+     * {@code hasAsyncQuestion} stops reporting the target BUSY — see
+     * {@code unansweredAsyncQuestionReturnsTheTicketToPendingAndReleasesItsTarget} above), which used
+     * to also erase the one signal {@code askAnsweredAsyncTasks} needed to recognize the worker's
+     * eventual real {@code fleet_reply}. That reply then had nowhere to land but the inbox, and
+     * {@code fleet_poll{ticket}} stayed PENDING forever — later force-failed with the false reason
+     * "session released before it replied", even though the worker had, in fact, replied.
+     */
+    @Test
+    void aReplyAfterAnAskTimeoutStillCompletesTheAsyncTicket() throws Exception {
+        String ticket = messages.sendAsync(T, "task that asks then finishes alone");
+        awaitWaiting();
+        injectDelivery();
+
+        assertEquals(MessageService.AskOutcome.TIMED_OUT,
+                messages.ask(T, "which config?", 200).outcome());
+        assertEquals(MessageService.Phase.PENDING, messages.poll(ticket).phase(),
+                "only the question wait ended; the delegated turn may still finish");
+
+        // The worker keeps working past the timeout and only now calls fleet_reply — with no live
+        // rendezvous waiter open (ask()'s timeout already closed it) and no new send() having
+        // reopened one for this target.
+        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(),
+                "fleet_poll{ticket} must return the worker's real reply, not stay pending forever");
+        assertEquals("reply", done.replySource());
+        assertFalse(messages.hasStrandedReply(T),
+                "the reply completed its own ticket directly and never touched the inbox");
+    }
+
+    /**
+     * 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
+     * be dispatched to the same target and itself go on to ask-and-lapse before the first worker's
+     * real reply ever arrives. Two open tasks are then both eligible candidates on one target with
+     * no live waiter to disambiguate them. A reply arriving now must not guess which one it answers
+     * — guessing wrong would hand the lead a plausible-looking answer to a delegation the worker
+     * never touched, worse than a failure because the lead acts on it — so it must fall back to the
+     * inbox exactly as the zero-candidate case does.
+     */
+    @Test
+    void twoAskTimedOutTicketsOnOneTargetFallBackToTheInboxRatherThanGuess() throws Exception {
+        String ticket1 = messages.sendAsync(T, "first task that asks");
+        awaitWaiting();
+        injectDelivery();
+        assertEquals(MessageService.AskOutcome.TIMED_OUT, messages.ask(T, "Q1?", 200).outcome());
+
+        String ticket2 = messages.sendAsync(T, "second task that asks");
+        awaitWaiting();
+        injectDelivery();
+        assertEquals(MessageService.AskOutcome.TIMED_OUT, messages.ask(T, "Q2?", 200).outcome());
+
+        assertTrue(messages.reply(T, "which task does this answer?"));
+
+        assertEquals(MessageService.Phase.PENDING, messages.poll(ticket1).phase(),
+                "an ambiguous reply must not guess ticket1");
+        assertEquals(MessageService.Phase.PENDING, messages.poll(ticket2).phase(),
+                "an ambiguous reply must not guess ticket2");
+        assertTrue(messages.hasStrandedReply(T));
+        var drained = messages.drainReplies(T);
+        assertEquals(1, drained.size());
+        assertEquals("which task does this answer?", drained.get(0).content());
+    }
+
     @Test
     void asyncQuestionBelongsToTheTaskThatOwnsItsForwardWaiter() throws Exception {
         String first = messages.sendAsync(T, "first task");

fleetd/src/test/java/dev/ltms/fleet/rest/FleetAppTest.java

@@ -415,7 +415,11 @@ class FleetAppTest {
         FakeHerdr herdr = new FakeHerdr().agentNameTakenTimes(99);
         int port = start(herdr, "http://gx00.gw:8000", Set.of("gx00.gw"));
 
-        assertEquals(500, req(port, "POST", "/members").statusCode());
+        // fleetd #304: 502, not Javalin's default 500 — the herdr failure is named, and the body
+        // carries herdr's own message, matching what fleet_spawn reports for the same failure.
+        HttpResponse<String> res = req(port, "POST", "/members");
+        assertEquals(502, res.statusCode());
+        assertEquals("herdr_error", mapper.readTree(res.body()).get("error").asText());
         assertTrue(herdr.called("tab.create"), "a tab was created before the failed start");
         assertEquals("w9:t2", params(herdr, "tab.close").get("tab_id"), "orphaned tab must be closed");
     }
@@ -733,7 +737,12 @@ class FleetAppTest {
         int port = start(herdr, "http://gx00.gw:8000", Set.of("gx00.gw"));
 
         // A genuine teardown failure must surface, not be reported as a successful 204.
-        assertEquals(500, req(port, "DELETE", "/members/w9:pW").statusCode());
+        // fleetd #304: it surfaces as a named 502 rather than Javalin's default 500. The property
+        // this test guards is "not 204" and the herdr detail reaching the caller — a bare 500 gave
+        // the body "Server Error" and said nothing about herdr.
+        HttpResponse<String> res = req(port, "DELETE", "/members/w9:pW");
+        assertEquals(502, res.statusCode());
+        assertEquals("herdr_error", mapper.readTree(res.body()).get("error").asText());
         assertFalse(herdr.called("tab.close"), "tab is not removed when the pane close failed");
     }
 
@@ -746,4 +755,5 @@ class FleetAppTest {
         assertEquals(204, req(port, "DELETE", "/members/w9:pW").statusCode());
         assertTrue(herdr.called("tab.close"));
     }
+
 }

fleetd/src/test/java/dev/ltms/fleet/session/GitWorktreesTest.java

@@ -403,6 +403,52 @@ class GitWorktreesTest {
         assertTrue(heads.isBlank(), "the branch leaked after a post-creation step threw:\n" + heads);
     }
 
+    /**
+     * fleetd #309. The add runner is a narrow seam for the case where Git has created state but
+     * the caller then kills the process. The runner first performs the real add in this throwaway
+     * repo, then throws the same kind of exception that {@link GitWorktrees#exec} uses for a timeout.
+     * This proves the failure path cleans both real Git objects without waiting for a slow checkout.
+     */
+    @Test
+    void addCleansUpWhenTheWorktreeAddRunnerFailsAfterCreatingState(@TempDir Path tmp) throws Exception {
+        Path repo = initRepo(tmp.resolve("repo"));
+        String branch = "cb-309-timeout";
+        WorktreeException timeout = new WorktreeException("command timed out: synthetic git worktree add");
+        AtomicReference<String> createdPath = new AtomicReference<>();
+        GitWorktrees worktrees = new GitWorktrees(tmp.resolve("wts").toString(), null, null, null, command -> {
+            createdPath.set(command[5]);
+            try {
+                git(repo, "worktree", "add", command[5], "-b", command[7], command[8]);
+            } catch (Exception e) {
+                throw new AssertionError("test setup could not create the worktree", e);
+            }
+            throw timeout;
+        });
+
+        WorktreeException thrown = assertThrows(WorktreeException.class,
+                () -> worktrees.add(repo.toString(), branch, "HEAD"));
+
+        assertSame(timeout, thrown, "cleanup must not replace the add failure");
+        assertNotNull(createdPath.get(), "the add runner must receive the worktree path");
+        assertFalse(Files.exists(Path.of(createdPath.get())),
+                "the worktree directory leaked after the add runner failed");
+        assertFalse(refExists(repo, "refs/heads/" + branch), "the branch leaked after the add runner failed");
+    }
+
+    /** An ordinary Git refusal must not delete the existing branch or log a cleanup warning. */
+    @Test
+    void addFailureBeforeCreatingAWorktreeIsQuiet(@TempDir Path tmp) throws Exception {
+        Path repo = initRepo(tmp.resolve("repo"));
+        String branch = "already-exists";
+        git(repo, "branch", branch);
+
+        assertThrows(WorktreeException.class, () -> new GitWorktrees(tmp.resolve("wts").toString())
+                .add(repo.toString(), branch, "HEAD"));
+
+        assertTrue(refExists(repo, "refs/heads/" + branch), "the existing branch must remain");
+        assertTrue(capturedMessages().isEmpty(), "an ordinary Git refusal logged a warning: " + capturedMessages());
+    }
+
     // ---- CB-189: broader remote-URL coverage — every remote, both fetch and push URLs, any
     // non-SSH scheme. Reporting only, additive to the origin/https strip-and-refuse tests above. ----
 

fleetd/src/test/java/dev/ltms/fleet/session/SessionManagerTest.java

@@ -26,7 +26,12 @@ import org.slf4j.LoggerFactory;
 import java.util.List;
 import java.util.Map;
 import java.util.Set;
+import java.util.concurrent.CountDownLatch;
+import java.util.concurrent.ExecutorService;
+import java.util.concurrent.Executors;
+import java.util.concurrent.Future;
 import java.util.concurrent.TimeUnit;
+import java.util.concurrent.atomic.AtomicInteger;
 import java.util.function.LongSupplier;
 
 import static org.junit.jupiter.api.Assertions.*;
@@ -178,14 +183,19 @@ class SessionManagerTest {
     }
 
     private SessionManager sessionManager(FakeHerdr herdr, LongSupplier clock, int contextCap,
-                                          boolean clearAfterTurn) {
+                                           boolean clearAfterTurn) {
+        return sessionManager(herdr, clock, contextCap, clearAfterTurn, null);
+    }
+
+    private SessionManager sessionManager(FakeHerdr herdr, LongSupplier clock, int contextCap,
+                                           boolean clearAfterTurn, java.util.function.Consumer<MemberSession> hook) {
         FleetConfig.Profile cfg = new FleetConfig.Profile(
                 "ltms-local", "http://gx00.gw:8000", "coder", null, "FLEETD_WORKER_TOKEN",
                 List.of("ccs", "ltms-local"), "tab", "fleetd-workers",
                 "worker: {profile} #{n}", null, null, null);
         ClaudeCodeLauncher workers = new ClaudeCodeLauncher(new AgentControl(herdr), new WorkspaceControl(herdr),
                 new SubscriptionGuard(Set.of("gx00.gw")), Map.of(cfg.profile(), cfg), cfg.profile(), _ -> null);
-        return new SessionManager(workers, new GitWorktrees(), clock, contextCap, clearAfterTurn);
+        return new SessionManager(workers, new GitWorktrees(), clock, contextCap, clearAfterTurn, hook);
     }
 
     @Test
@@ -670,6 +680,24 @@ class SessionManagerTest {
                 "BUSY session remains");
     }
 
+    @Test
+    void reapIdleDoesNotReleaseSessionDeliveredAfterItsEligibilityCheck() {
+        long[] clock = {0};
+        FakeHerdr herdr = new FakeHerdr();
+        SessionManager[] manager = new SessionManager[1];
+        SessionManager sessions = sessionManager(herdr, () -> clock[0], 0, false,
+                session -> manager[0].onDelivered(session.terminalId(), TestTurnTokens.inert(session.terminalId())));
+        manager[0] = sessions;
+        MemberSession session = sessions.acquire("ltms-local", null, "/caller", "term_primary");
+        sessions.asPresence().markPresent(session.terminalId());
+
+        clock[0] = 11;
+        assertEquals(0, sessions.reapIdle(10), "delivery replaces the idle snapshot before release");
+        assertEquals(MemberSession.State.BUSY, sessions.get(session.paneId()).orElseThrow().state(),
+                "a just-delivered session stays registered and busy");
+        assertFalse(herdr.called("pane.close"), "the busy session pane is not stopped");
+    }
+
     @Test
     void doneSessionPastIdleTtlIsReaped() {
         long[] clock = {0};
@@ -824,6 +852,186 @@ class SessionManagerTest {
                 .count();
     }
 
+    // --- fleetd #308: a spawn accepted while the shutdown drain is running must not orphan ---
+
+    @Test
+    void acquireRefusesANewSpawnOnceDrainAllHasStarted() {
+        FakeHerdr herdr = new FakeHerdr();
+        SessionManager sessions = sessionManager(herdr);
+
+        sessions.drainAll(TimeUnit.MILLISECONDS.toNanos(50)); // empty roster — returns immediately,
+        // but the shutdown guard it flips must stay tripped for the life of the process.
+
+        ShuttingDownException e = assertThrows(ShuttingDownException.class,
+                () -> sessions.acquire("ltms-local", null, "/caller", "term_primary"),
+                "a spawn requested after the drain has begun must be refused loudly (invariant 3), "
+                        + "not silently registered into a registry the drain will never revisit");
+        assertNotNull(e.getMessage());
+        assertFalse(e.getMessage().isBlank(), "the refusal must say why, not just that it failed");
+        assertTrue(sessions.roster().isEmpty(), "the refused spawn must never reach the registry");
+    }
+
+    /**
+     * fleetd #308: the guard above closes most of the shutdown-race window, but it cannot close
+     * all of it — a caller that already passed the {@code draining} check before {@code drainAll}
+     * flips it can still be mid-{@code launcher.spawn()} (a real herdr round trip, not
+     * instantaneous) when {@code drainAll} takes its registry snapshot. This test forces exactly
+     * that interleaving with a launcher double that blocks the second {@code spawn()} call and the
+     * first {@code stop()} call until released, then proves the post-loop sweep in {@code
+     * drainAll} still finds and tears down the straggler that lands in the registry afterward.
+     */
+    @Test
+    void drainAllSweepsAStragglerThatRegisteredAfterTheInitialSnapshot() throws Exception {
+        FakeHerdr herdr = new FakeHerdr();
+        FleetConfig.Profile cfg = new FleetConfig.Profile(
+                "ltms-local", "http://gx00.gw:8000", "coder", null, "FLEETD_WORKER_TOKEN",
+                List.of("ccs", "ltms-local"), "tab", "fleetd-workers",
+                "worker: {profile} #{n}", null, null, null);
+        ClaudeCodeLauncher delegate = new ClaudeCodeLauncher(new AgentControl(herdr), new WorkspaceControl(herdr),
+                new SubscriptionGuard(Set.of("gx00.gw")), Map.of(cfg.profile(), cfg), cfg.profile(), _ -> null);
+        RaceLauncher race = new RaceLauncher(delegate);
+        SessionManager sessions = new SessionManager(race);
+
+        // Registered normally, before the drain starts — the first spawn call, never blocked.
+        MemberSession ready = sessions.acquire("ltms-local", "/ready", "/caller", "ownerR");
+
+        ExecutorService exec = Executors.newFixedThreadPool(2);
+        try {
+            // The straggler's acquire() reads `draining == false` (checked before this call ever
+            // touches the launcher) and then blocks inside its own spawn() — the second spawn call.
+            Future<MemberSession> straggler = exec.submit(() ->
+                    sessions.acquire("ltms-local", "/late", "/caller", "ownerLate"));
+
+            assertTrue(race.enteredSecondSpawn.await(5, TimeUnit.SECONDS),
+                    "the straggler must have passed the shutdown guard and reached spawn() before "
+                            + "drainAll ever runs");
+            assertEquals(1, sessions.roster().size(),
+                    "the straggler is still inside spawn() — not registered yet");
+
+            // drainAll flips `draining`, snapshots the registry (only `ready` is in it), and starts
+            // releasing that snapshot — its first release() call stops `ready`'s pane, which this
+            // launcher double blocks on so the interleaving below is deterministic, not a timing bet.
+            Future<?> drain = exec.submit(() -> sessions.drainAll(TimeUnit.SECONDS.toNanos(5)));
+
+            assertTrue(race.enteredFirstStop.await(5, TimeUnit.SECONDS),
+                    "drainAll must be stopping the ready session's pane — proof its initial "
+                            + "registry snapshot has already been taken");
+
+            // Only now does the straggler's spawn complete and register — strictly after the
+            // snapshot drainAll's main pass is working from.
+            race.releaseSecondSpawn.countDown();
+            MemberSession registered = straggler.get(5, TimeUnit.SECONDS);
+
+            // Let drainAll finish releasing `ready`; it then re-checks the registry and must find
+            // (and drain) the straggler that just landed in it.
+            race.releaseFirstStop.countDown();
+            drain.get(5, TimeUnit.SECONDS);
+
+            assertTrue(sessions.roster().isEmpty(),
+                    "the post-loop sweep must drain the straggler too, not just the initial snapshot");
+            assertNotNull(registered.paneId());
+            long paneCloseCalls = herdr.calls.stream().filter(c -> "pane.close".equals(c.method())).count();
+            assertEquals(2, paneCloseCalls,
+                    "both ready's pane AND the straggler's pane must actually be stopped — a pane "
+                            + "left running is exactly the orphan this ticket is about");
+        } finally {
+            exec.shutdownNow();
+        }
+    }
+
+    /**
+     * Delegates every call while blocking the SECOND {@code spawn()} call and the FIRST
+     * {@code stop()} call until the test releases them — used to force the fleetd #308 race
+     * deterministically instead of betting on real thread-scheduling timing.
+     */
+    private static final class RaceLauncher implements PeerLauncher {
+        private final PeerLauncher delegate;
+        private final AtomicInteger spawnCalls = new AtomicInteger();
+        private final AtomicInteger stopCalls = new AtomicInteger();
+        final CountDownLatch enteredSecondSpawn = new CountDownLatch(1);
+        final CountDownLatch releaseSecondSpawn = new CountDownLatch(1);
+        final CountDownLatch enteredFirstStop = new CountDownLatch(1);
+        final CountDownLatch releaseFirstStop = new CountDownLatch(1);
+
+        RaceLauncher(PeerLauncher delegate) {
+            this.delegate = delegate;
+        }
+
+        private static void awaitOrFail(CountDownLatch latch) {
+            try {
+                if (!latch.await(5, TimeUnit.SECONDS)) {
+                    throw new AssertionError("RaceLauncher latch timed out");
+                }
+            } catch (InterruptedException e) {
+                Thread.currentThread().interrupt();
+                throw new AssertionError("RaceLauncher latch interrupted", e);
+            }
+        }
+
+        @Override
+        public Set<Capability> capabilities() {
+            return delegate.capabilities();
+        }
+
+        @Override
+        public Set<Capability> capabilitiesFor(String profileName) {
+            return delegate.capabilitiesFor(profileName);
+        }
+
+        @Override
+        public PeerHandle spawn(SpawnRequest req) {
+            if (spawnCalls.incrementAndGet() == 2) {
+                enteredSecondSpawn.countDown();
+                awaitOrFail(releaseSecondSpawn);
+            }
+            return delegate.spawn(req);
+        }
+
+        @Override
+        public Set<String> profiles() {
+            return delegate.profiles();
+        }
+
+        @Override
+        public String defaultProfile() {
+            return delegate.defaultProfile();
+        }
+
+        @Override
+        public String effectiveCwd(SpawnRequest req) {
+            return delegate.effectiveCwd(req);
+        }
+
+        @Override
+        public List<String> parityOverlay(String profileName) {
+            return delegate.parityOverlay(profileName);
+        }
+
+        @Override
+        public List<?> list() {
+            return delegate.list();
+        }
+
+        @Override
+        public int reapOrphanWorkers() {
+            return delegate.reapOrphanWorkers();
+        }
+
+        @Override
+        public void stop(String id) {
+            if (stopCalls.incrementAndGet() == 1) {
+                enteredFirstStop.countDown();
+                awaitOrFail(releaseFirstStop);
+            }
+            delegate.stop(id);
+        }
+
+        @Override
+        public boolean clearContext(String id) {
+            return delegate.clearContext(id);
+        }
+    }
+
     private static List<String> promptTexts(FakeHerdr herdr) {
         return herdr.calls.stream()
                 .filter(c -> "agent.prompt".equals(c.method()))