diff --git a/SimpleAPI/src/main/java/com/bencodez/simpleapi/servercomm/http/HttpProxyTransportServer.java b/SimpleAPI/src/main/java/com/bencodez/simpleapi/servercomm/http/HttpProxyTransportServer.java
index 2b2894a..ce319c5 100644
--- a/SimpleAPI/src/main/java/com/bencodez/simpleapi/servercomm/http/HttpProxyTransportServer.java
+++ b/SimpleAPI/src/main/java/com/bencodez/simpleapi/servercomm/http/HttpProxyTransportServer.java
@@ -242,6 +242,55 @@ public boolean send(String serverId, String deliveryId, JsonEnvelope envelope) {
 		return send(serverId, deliveryId, envelope, false);
 	}
 
+	/**
+	 * Returns whether this server still owns any durable proxy-to-backend
+	 * delivery, including a publication whose durability is awaiting a same-ID
+	 * retry. Callers can use this before retiring the HTTP transport so accepted
+	 * work is not stranded solely because another transport was configured.
+	 */
+	public boolean hasPendingDeliveries() {
+		if (durableOutgoing != null) return durableOutgoing.hasPendingDeliveries();
+		synchronized (backends) {
+			for (BackendState backend : backends.values()) {
+				if (backend.hasPendingOutgoing()) return true;
+			}
+		}
+		return false;
+	}
+
+	/**
+	 * Returns whether a stopped server's durable outgoing directory contains any
+	 * delivery state. This is intentionally conservative: an unexpected entry is
+	 * reported as pending so callers do not switch transports and strand data
+	 * before the normal queue loader can validate or recover it.
+	 */
+	public static boolean hasPersistedDeliveries(Path outgoingDirectory) throws IOException {
+		if (outgoingDirectory == null) throw new IllegalArgumentException("HTTP outgoing queue directory is required");
+		Path root = outgoingDirectory.toAbsolutePath().normalize();
+		java.nio.file.attribute.BasicFileAttributes rootAttributes;
+		try {
+			rootAttributes = Files.readAttributes(root, java.nio.file.attribute.BasicFileAttributes.class,
+					LinkOption.NOFOLLOW_LINKS);
+		} catch (java.nio.file.NoSuchFileException absent) {
+			return false;
+		}
+		if (rootAttributes.isSymbolicLink() || !rootAttributes.isDirectory())
+			throw new IOException("HTTP outgoing queue directory is invalid");
+		int backendCount = 0;
+		try (DirectoryStream<Path> backends = Files.newDirectoryStream(root)) {
+			for (Path backend : backends) {
+				if (Files.isSymbolicLink(backend) || !Files.isDirectory(backend, LinkOption.NOFOLLOW_LINKS))
+					throw new IOException("HTTP outgoing queue contains an invalid entry");
+				if (++backendCount > MAX_BACKENDS)
+					throw new IOException("HTTP outgoing queue exceeds its backend bound");
+				try (DirectoryStream<Path> entries = Files.newDirectoryStream(backend)) {
+					if (entries.iterator().hasNext()) return true;
+				}
+			}
+		}
+		return false;
+	}
+
 	private boolean send(String serverId, String deliveryId, JsonEnvelope envelope, boolean generatedId) {
 		if (closed || serverId == null || envelope == null) return false;
 		try {
@@ -563,6 +612,7 @@ private BackendState(String serverId, DurableOutgoingQueue durableOutgoing,
 		private synchronized void restore(Collection<HttpTransportProtocol.Delivery> deliveries) {
 			for (HttpTransportProtocol.Delivery delivery : deliveries) outgoing.put(delivery.id(), delivery);
 		}
+		private synchronized boolean hasPendingOutgoing() { return !outgoing.isEmpty(); }
 		private boolean beginPoll(String requestedSession) { synchronized (this) { if (retired || activePoll) return false; activePoll = true; touch(); return true; } }
 		private void endPoll() { synchronized (this) { activePoll = false; touch(); notifyAll(); } }
 		boolean beginPollForTest() { return beginPoll("test"); }
@@ -941,6 +991,16 @@ private synchronized boolean hasQuarantined(String serverId) throws IOException
 			return quarantined != null && !quarantined.isEmpty();
 		}
 
+		synchronized boolean hasPendingDeliveries() {
+			for (Map<String, Path> serverFiles : files.values()) {
+				if (!serverFiles.isEmpty()) return true;
+			}
+			for (Map<String, Path> quarantined : quarantinedFiles.values()) {
+				if (!quarantined.isEmpty()) return true;
+			}
+			return false;
+		}
+
 		/** Deletes only a validated, observed-empty backend directory and makes its removal durable. */
 		private void deleteVerifiedEmptyDirectory(Path directory) throws IOException {
 			if (Files.isSymbolicLink(directory) || !Files.isDirectory(directory, LinkOption.NOFOLLOW_LINKS)
diff --git a/SimpleAPI/src/test/java/com/bencodez/simpleapi/servercomm/http/HttpTransportRuntimeTest.java b/SimpleAPI/src/test/java/com/bencodez/simpleapi/servercomm/http/HttpTransportRuntimeTest.java
index e218556..2cbf217 100644
--- a/SimpleAPI/src/test/java/com/bencodez/simpleapi/servercomm/http/HttpTransportRuntimeTest.java
+++ b/SimpleAPI/src/test/java/com/bencodez/simpleapi/servercomm/http/HttpTransportRuntimeTest.java
@@ -40,6 +40,42 @@ void publicConstructorsRequireDurableOutgoingDirectory() throws Exception {
 				null, ignored -> { }, (serverId, deliveryId) -> { }));
 	}
 
+	@Test
+	void pendingDeliveryStateTracksDurableQueueUntilAcknowledgement() throws Exception {
+		HttpTlsIdentity identity = HttpTlsIdentity.loadOrCreate(directory.resolve("pending-proxy"), "localhost");
+		HttpEnrollmentAuthority authority = new HttpEnrollmentAuthority(identity, directory.resolve("pending-authority"));
+		try (HttpProxyTransportServer server = new HttpProxyTransportServer(new InetSocketAddress("localhost", 0),
+				identity, authority, directory.resolve("pending-outgoing"), ignored -> { })) {
+			assertFalse(server.hasPendingDeliveries());
+			String deliveryId = java.util.UUID.randomUUID().toString();
+			assertTrue(server.send("lobby-1", deliveryId, JsonEnvelope.builder("ordinary").build()));
+			assertTrue(server.hasPendingDeliveries());
+
+			server.backendStateForTest("lobby-1").acknowledge(java.util.List.of(deliveryId));
+
+			assertFalse(server.hasPendingDeliveries());
+		}
+	}
+
+	@Test
+	void persistedDeliveryStateCanBeCheckedBeforeServerStartup() throws Exception {
+		Path outgoing = directory.resolve("stopped-outgoing");
+		assertFalse(HttpProxyTransportServer.hasPersistedDeliveries(outgoing));
+		Files.createDirectories(outgoing.resolve("lobby-1"));
+		assertFalse(HttpProxyTransportServer.hasPersistedDeliveries(outgoing));
+		Files.writeString(outgoing.resolve("lobby-1").resolve(".pending-delivery.json"), "pending");
+		assertTrue(HttpProxyTransportServer.hasPersistedDeliveries(outgoing));
+	}
+
+	@Test
+	void inaccessiblePersistedDeliveryLocationIsNotReportedAsAbsent() throws Exception {
+		Path nonDirectoryParent = directory.resolve("queue-parent-file");
+		Files.writeString(nonDirectoryParent, "not a directory");
+
+		assertThrows(java.io.IOException.class,
+				() -> HttpProxyTransportServer.hasPersistedDeliveries(nonDirectoryParent.resolve("outgoing")));
+	}
+
 	@Test
 	void endpointHelperSupportsIpv6Literals() throws Exception {
 		HttpTlsIdentity identity = HttpTlsIdentity.loadOrCreate(directory.resolve("ipv6-proxy"), "::1");
@@ -275,6 +311,8 @@ void publishedOutgoingDeliveryRemainsTrackedUntilDurabilityCanBeConfirmed() thro
 				JsonEnvelope.builder("durable").build());
 
 		assertFalse(state.enqueue(delivery), "post-publication failure must not confirm durable acceptance");
+		assertTrue(queue.hasPendingDeliveries(),
+				"an ambiguous published file must keep the HTTP transport retained");
 		assertTrue(state.await("lobby-1", java.util.UUID.randomUUID().toString(), 0).messages().isEmpty(),
 				"an uncertain publication must remain hidden until its durability retry succeeds");
 		assertEquals(1L, countRegularFiles(queueRoot));