diff --git a/core/libs/prx/libkernel/System/src/Exception.cpp b/core/libs/prx/libkernel/System/src/Exception.cpp
index a1314a8a74..095f8b5ad9 100644
--- a/core/libs/prx/libkernel/System/src/Exception.cpp
+++ b/core/libs/prx/libkernel/System/src/Exception.cpp
@@ -784,7 +784,7 @@ Attempt TryDeliver(Pthread thread, HANDLE native, GuestExceptionHandler handler,
         DWORD64 unknown = 0;
         if (arm != nullptr && running == CodeKind::Host && !restoring) ArmReturnBreak(native, delivery.context, queued, *arm, unknown);
         ResumeThread(native);
-        if (postAfterResume) TimedWait::QueueForDeliveryDrain(GetThreadId(native), &DeferredWaitingEntry, queued);
+        if (postAfterResume) TimedWait::QueueForDeliveryDrain(GetThreadId(native), &thread->_finished, &DeferredWaitingEntry, queued);
         if (running == CodeKind::Unknown) {
             static_cast<void>(ClassifyImage(image));
             continue;
diff --git a/core/libs/prx/libkernel/Time/TimedWait.cpp b/core/libs/prx/libkernel/Time/TimedWait.cpp
index 81f6958169..299ba46b1b 100644
--- a/core/libs/prx/libkernel/Time/TimedWait.cpp
+++ b/core/libs/prx/libkernel/Time/TimedWait.cpp
@@ -170,9 +170,26 @@ struct Waiter {
     }
 };
 
-void QueueForDeliveryDrain(unsigned long thread, void (*run)(void*), void* argument) {
-    const std::lock_guard lock(drainBoxesLock);
-    drainBoxes[thread].push_back({run, argument});
+std::atomic<void (*)()>& DrainPostHook() {
+    static std::atomic<void (*)()> hook{nullptr};
+    return hook;
+}
+
+void SetDeliveryDrainPostHook(void (*hook)()) {
+    DrainPostHook().store(hook, std::memory_order_release);
+}
+
+void QueueForDeliveryDrain(unsigned long thread, const std::atomic<bool>* targetFinished, void (*run)(void*), void* argument) {
+    if (const auto hook = DrainPostHook().load(std::memory_order_acquire)) hook();
+    bool queued = false;
+    {
+        const std::lock_guard lock(drainBoxesLock);
+        if (targetFinished == nullptr || !targetFinished->load(std::memory_order_acquire)) {
+            drainBoxes[thread].push_back({run, argument});
+            queued = true;
+        }
+    }
+    if (!queued) run(argument);
 }
 
 void ReapDeliveryDrain() {
diff --git a/core/libs/prx/libkernel/Time/include/TimedWait.hpp b/core/libs/prx/libkernel/Time/include/TimedWait.hpp
index f81890fb58..e072e1a860 100644
--- a/core/libs/prx/libkernel/Time/include/TimedWait.hpp
+++ b/core/libs/prx/libkernel/Time/include/TimedWait.hpp
@@ -39,9 +39,10 @@ public:
 void DeliverDeferred();
 
 #ifdef _WIN32
-void QueueForDeliveryDrain(unsigned long thread, void (*run)(void*), void* argument);
+void QueueForDeliveryDrain(unsigned long thread, const std::atomic<bool>* targetFinished, void (*run)(void*), void* argument);
 void ReapDeliveryDrain();
 std::size_t DeliveryDrainPending();
+void SetDeliveryDrainPostHook(void (*hook)());
 
 constexpr unsigned PARK_SPINS = 1000;
 
diff --git a/core/libs/tests/GuestRaiseException.cpp b/core/libs/tests/GuestRaiseException.cpp
index 4c7e245c67..5079190b40 100644
--- a/core/libs/tests/GuestRaiseException.cpp
+++ b/core/libs/tests/GuestRaiseException.cpp
@@ -308,6 +308,14 @@ static void* APS5_VABI ChurnUntil(void* arg) {
     while (!exitingRelease.load()) MultiByteToWideChar(CP_UTF8, 0, source.data(), static_cast<int>(source.size()), converted.data(), static_cast<int>(converted.size()));
     return nullptr;
 }
+
+static std::atomic<int> postEntered{0};
+static std::atomic<bool> postHold{false};
+
+static void DeliveryPostHook() {
+    postEntered.fetch_add(1);
+    while (postHold.load()) std::this_thread::yield();
+}
 #endif
 
 static std::atomic<std::thread::id> spinningId;
@@ -742,6 +750,8 @@ int main() {
 
     Worker churning;
     Pthread churningThread = nullptr;
+    TimedWait::SetDeliveryDrainPostHook(&DeliveryPostHook);
+    const int postsBeforeChurn = postEntered.load();
     Require(scePthreadCreate(&churningThread, nullptr, Churning, &churning, "churn then drain") == 0);
     for (int round = 0; round < DrainRounds; ++round) {
         while (!churning.started.load()) std::this_thread::yield();
@@ -753,6 +763,7 @@ int main() {
         ExpectDelivery(before, churning.id);
     }
     Require(scePthreadJoin(churningThread, nullptr) == 0);
+    Require(postEntered.load() > postsBeforeChurn);
 
     for (int round = 0; round < ExitRounds; ++round) {
         exitingRelease.store(false);
@@ -767,6 +778,35 @@ int main() {
         Require(scePthreadJoin(exitingThread, nullptr) == 0);
         Require(TimedWait::DeliveryDrainPending() == 0);
     }
+
+    exitingRelease.store(false);
+    postHold.store(true);
+    const int postsBeforeHeld = postEntered.load();
+    Worker heldExit;
+    Pthread heldExitThread = nullptr;
+    Require(scePthreadCreate(&heldExitThread, nullptr, ChurnUntil, &heldExit, "exit while posted") == 0);
+    while (!heldExit.started.load()) std::this_thread::yield();
+    std::this_thread::sleep_for(std::chrono::milliseconds(20));
+    std::atomic<int> raiseResult{-1};
+    bool posted = false;
+    for (int attempt = 0; attempt < 50 && !posted; ++attempt) {
+        raiseResult.store(-1);
+        std::thread raiser([&] { raiseResult.store(sceKernelRaiseException(heldExitThread, GUEST_SIGUSR1)); });
+        const auto entered = std::chrono::steady_clock::now() + std::chrono::seconds(2);
+        while (postEntered.load() == postsBeforeHeld && raiseResult.load() == -1 && std::chrono::steady_clock::now() < entered) std::this_thread::yield();
+        posted = postEntered.load() > postsBeforeHeld;
+        if (posted) {
+            exitingRelease.store(true);
+            Require(scePthreadJoin(heldExitThread, nullptr) == 0);
+            postHold.store(false);
+        }
+        raiser.join();
+    }
+    Require(posted);
+    Require(raiseResult.load() == 0 || raiseResult.load() == SCE_KERNEL_ERROR_ESRCH);
+    const auto drained = std::chrono::steady_clock::now() + std::chrono::seconds(2);
+    while (TimedWait::DeliveryDrainPending() != 0 && std::chrono::steady_clock::now() < drained) std::this_thread::yield();
+    Require(TimedWait::DeliveryDrainPending() == 0);
     std::this_thread::sleep_for(std::chrono::milliseconds(200));
     const int settledCalls = calls.load();
     drainingRound.store(0);