diff --git a/httpcore5/src/main/java/org/apache/hc/core5/pool/StrictConnPool.java b/httpcore5/src/main/java/org/apache/hc/core5/pool/StrictConnPool.java
index 15eb844e5..2a6751745 100644
--- a/httpcore5/src/main/java/org/apache/hc/core5/pool/StrictConnPool.java
+++ b/httpcore5/src/main/java/org/apache/hc/core5/pool/StrictConnPool.java
@@ -596,6 +596,7 @@ public void enumAvailable(final Callback<PoolEntry<T, C>> callback) {
         } finally {
             this.lock.unlock();
         }
+        fireCallbacks();
     }
 
     /**
@@ -615,6 +616,7 @@ public void enumLeased(final Callback<PoolEntry<T, C>> callback) {
         } finally {
             this.lock.unlock();
         }
+        fireCallbacks();
     }
 
     private void purgePoolMap() {
diff --git a/httpcore5/src/test/java/org/apache/hc/core5/pool/TestPoolPendingRequestExpiry.java b/httpcore5/src/test/java/org/apache/hc/core5/pool/TestPoolPendingRequestExpiry.java
new file mode 100644
index 000000000..383e439e3
--- /dev/null
+++ b/httpcore5/src/test/java/org/apache/hc/core5/pool/TestPoolPendingRequestExpiry.java
@@ -0,0 +1,102 @@
+/*
+ * ====================================================================
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ * ====================================================================
+ *
+ * This software consists of voluntary contributions made by many
+ * individuals on behalf of the Apache Software Foundation.  For more
+ * information on the Apache Software Foundation, please see
+ * <http://www.apache.org/>.
+ *
+ */
+package org.apache.hc.core5.pool;
+
+import static org.junit.jupiter.api.Assertions.assertInstanceOf;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+import java.util.concurrent.ExecutionException;
+import java.util.concurrent.Future;
+import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
+
+import org.apache.hc.core5.io.CloseMode;
+import org.apache.hc.core5.util.TimeValue;
+import org.apache.hc.core5.util.Timeout;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.EnumSource;
+
+final class TestPoolPendingRequestExpiry {
+
+    private static ManagedConnPool<String, FakeConnection> createPool(final PoolConcurrencyPolicy policy) {
+        switch (policy) {
+            case STRICT:
+                return new StrictConnPool<>(1, 1);
+            case LAX:
+                return new LaxConnPool<>(1);
+            default:
+                return new RouteSegmentedConnPool<>(
+                        1, 1, TimeValue.NEG_ONE_MILLISECOND, PoolReusePolicy.LIFO, (c, mode) -> c.close(mode));
+        }
+    }
+
+    @ParameterizedTest
+    @EnumSource(PoolConcurrencyPolicy.class)
+    void closeExpiredFailsExpiredPendingRequest(final PoolConcurrencyPolicy policy) throws Exception {
+        final ManagedConnPool<String, FakeConnection> pool = createPool(policy);
+        try {
+            final PoolEntry<String, FakeConnection> leased =
+                    pool.lease("r1", null, Timeout.ofSeconds(1), null).get(1, TimeUnit.SECONDS);
+            assertNotNull(leased);
+            final Future<PoolEntry<String, FakeConnection>> pending =
+                    pool.lease("r1", null, Timeout.ofMilliseconds(50), null);
+
+            Thread.sleep(150);
+            pool.closeExpired();
+
+            final ExecutionException ex = assertThrows(ExecutionException.class,
+                    () -> pending.get(5, TimeUnit.SECONDS));
+            assertInstanceOf(TimeoutException.class, ex.getCause());
+        } finally {
+            pool.close(CloseMode.IMMEDIATE);
+        }
+    }
+
+    @ParameterizedTest
+    @EnumSource(PoolConcurrencyPolicy.class)
+    void closeIdleFailsExpiredPendingRequest(final PoolConcurrencyPolicy policy) throws Exception {
+        final ManagedConnPool<String, FakeConnection> pool = createPool(policy);
+        try {
+            final PoolEntry<String, FakeConnection> leased =
+                    pool.lease("r1", null, Timeout.ofSeconds(1), null).get(1, TimeUnit.SECONDS);
+            assertNotNull(leased);
+            final Future<PoolEntry<String, FakeConnection>> pending =
+                    pool.lease("r1", null, Timeout.ofMilliseconds(50), null);
+
+            Thread.sleep(150);
+            pool.closeIdle(TimeValue.ofMilliseconds(1));
+
+            final ExecutionException ex = assertThrows(ExecutionException.class,
+                    () -> pending.get(5, TimeUnit.SECONDS));
+            assertInstanceOf(TimeoutException.class, ex.getCause());
+        } finally {
+            pool.close(CloseMode.IMMEDIATE);
+        }
+    }
+
+}