diff --git a/lightning/src/ln/channelmanager.rs b/lightning/src/ln/channelmanager.rs
index 6f411273aab..22dd2a6b099 100644
--- a/lightning/src/ln/channelmanager.rs
+++ b/lightning/src/ln/channelmanager.rs
@@ -15695,15 +15695,28 @@ where
 						},
 						None,
 					));
-					for (channel_htlc_source, payment_hash) in channel.inflight_htlc_sources() {
-						let mut found_htlc = false;
-						for (monitor_htlc_source, _) in monitor.get_all_current_outbound_htlcs() {
-							if *channel_htlc_source == monitor_htlc_source {
-								found_htlc = true;
-								break;
-							}
-						}
-						if !found_htlc {
+					// Collecting all outbound HTLC sources into a HashSet allows for efficient,
+					// O(1) average-time lookups. This also avoids a slow, nested O(n*m) loop later on.
+					let monitor_htlc_sources: HashSet<HTLCSource> = monitor
+						.get_all_current_outbound_htlcs()
+						.into_iter()
+						.map(|(source, _)| source)
+						.collect();
+
+					// Grouping all HTLCs from the `ChannelManager` by their
+					// `payment_hash`, ensures that we treat all identical HTLCs
+					// as a single logical unit, enabling us to fail them all immediately.
+					let mut htlcs_by_hash: HashMap<PaymentHash, Vec<HTLCSource>> = new_hash_map();
+					for (source, payment_hash) in channel.inflight_htlc_sources() {
+						htlcs_by_hash.entry(*payment_hash).or_default().push(source.clone());
+					}
+
+					for (payment_hash, htlc_sources) in htlcs_by_hash {
+						let is_any_htlc_missing = htlc_sources
+							.iter()
+							.any(|source| !monitor_htlc_sources.contains(source));
+
+						if is_any_htlc_missing {
 							// If we have some HTLCs in the channel which are not present in the newer
 							// ChannelMonitor, they have been removed and should be failed back to
 							// ensure we don't forget them entirely. Note that if the missing HTLC(s)
@@ -15714,17 +15727,24 @@ where
 							let logger = WithChannelContext::from(
 								&args.logger,
 								&channel.context,
-								Some(*payment_hash),
+								Some(payment_hash),
 							);
 							log_info!(logger,
-								"Failing HTLC with hash {} as it is missing in the ChannelMonitor for channel {} but was present in the (stale) ChannelManager",
-								&channel.context.channel_id(), &payment_hash);
-							failed_htlcs.push((
-								channel_htlc_source.clone(),
-								*payment_hash,
-								channel.context.get_counterparty_node_id(),
-								channel.context.channel_id(),
-							));
+								"Failing ALL HTLCs with hash {} as it is missing in the ChannelMonitor for channel {} but was present in the (stale) ChannelManager",
+								&payment_hash, &channel.context.channel_id());
+
+							// Since at least one HTLC was missing, we now
+							// iterate through the entire group we collected and add each one to the
+							// `failed_htlcs` list. This guarantees that all identical HTLCs are
+							// failed back at the same time, not just the single one we detected was missing.
+							for source in htlc_sources {
+								failed_htlcs.push((
+									source,
+									payment_hash,
+									channel.context.get_counterparty_node_id(),
+									channel.context.channel_id(),
+								));
+							}
 						}
 					}
 				} else {
diff --git a/lightning/src/ln/functional_tests.rs b/lightning/src/ln/functional_tests.rs
index 388db6d174f..5aa07f6ca5d 100644
--- a/lightning/src/ln/functional_tests.rs
+++ b/lightning/src/ln/functional_tests.rs
@@ -11717,3 +11717,78 @@ pub fn test_funding_signed_event() {
 	nodes[0].node.get_and_clear_pending_msg_events();
 	nodes[1].node.get_and_clear_pending_msg_events();
 }
+
+#[xtest(feature = "_externalize_tests")]
+pub fn test_stale_force_close_with_identical_htlcs() {
+	// This tests that if a peer force-closes with a stale
+	// state after we've received two identical HTLCs, we must fail back both
+	// of them immediately.
+
+	let chanmon_cfgs = create_chanmon_cfgs(3);
+	let node_cfgs = create_node_cfgs(3, &chanmon_cfgs);
+	let node_chanmgrs = create_node_chanmgrs(3, &node_cfgs, &[None, None, None]);
+	let nodes = create_network(3, &node_cfgs, &node_chanmgrs);
+
+	let chan_a_b = create_announced_chan_between_nodes(&nodes, 0, 1);
+	let _chan_b_c = create_announced_chan_between_nodes(&nodes, 1, 2);
+
+	let stale_tx = get_local_commitment_txn!(nodes[0], chan_a_b.2)[0].clone();
+
+	let (payment_preimage, payment_hash, _payment_secret, _payment_id_1) =
+		route_payment(&nodes[0], &[&nodes[1], &nodes[2]], 10_000);
+
+	*nodes[0].network_payment_count.borrow_mut() -= 1;
+	let (payment_preimage_2, payment_hash_2, _payment_secret_2, _payment_id_2) =
+		route_payment(&nodes[0], &[&nodes[1], &nodes[2]], 10_000);
+
+	assert_eq!(payment_hash, payment_hash_2, "Both HTLCs should have identical payment hashes");
+	assert_eq!(payment_preimage, payment_preimage_2, "Both HTLCs should have identical preimages");
+
+	mine_transaction(&nodes[1], &stale_tx);
+	check_added_monitors!(nodes[1], 1);
+
+	nodes[1].node.peer_disconnected(nodes[0].node.get_our_node_id());
+	nodes[1].node.peer_disconnected(nodes[2].node.get_our_node_id());
+
+	nodes[0]
+		.node
+		.peer_connected(
+			nodes[1].node.get_our_node_id(),
+			&msgs::Init {
+				features: nodes[1].node.init_features(),
+				networks: None,
+				remote_network_address: None,
+			},
+			true,
+		)
+		.unwrap();
+	nodes[2]
+		.node
+		.peer_connected(
+			nodes[1].node.get_our_node_id(),
+			&msgs::Init {
+				features: nodes[1].node.init_features(),
+				networks: None,
+				remote_network_address: None,
+			},
+			true,
+		)
+		.unwrap();
+
+	let events = nodes[1].node.get_and_clear_pending_msg_events();
+	let mut fail_htlc_count = 0;
+	for event in &events {
+		match event {
+			MessageSendEvent::UpdateHTLCs { updates, .. } => {
+				fail_htlc_count += updates.update_fail_htlcs.len();
+			},
+			_ => {},
+		}
+	}
+
+	assert_eq!(
+		fail_htlc_count, 2,
+		"Force-close immediately fails 2 committed HTLCs (expected). Got: {}",
+		fail_htlc_count
+	);
+}