diff --git a/src/Connection/ConnectionLimitingPool.php b/src/Connection/ConnectionLimitingPool.php
index 52c8f8ea..1bc38ea7 100644
--- a/src/Connection/ConnectionLimitingPool.php
+++ b/src/Connection/ConnectionLimitingPool.php
@@ -187,8 +187,9 @@ private function getStreamFor(string $uri, Request $request, Cancellation $cance
 
             $deferred = new DeferredFuture;
             $futureFromDeferred = $deferred->getFuture();
+            $deferredId = \spl_object_id($deferred);
 
-            $this->waiting[$uri][\spl_object_id($deferred)] = $deferred;
+            $this->waiting[$uri][$deferredId] = $deferred;
 
             if ($this->isAdditionalConnectionAllowed($uri)) {
                 break;
@@ -251,10 +252,10 @@ private function getStreamFor(string $uri, Request $request, Cancellation $cance
         } catch (CompositeException $exception) {
             [$exception] = $exception->getReasons(); // The first reason is why the connection failed.
             throw $exception;
+        } finally {
+            $this->removeWaiting($uri, $deferredId); // DeferredFuture no longer needed for this request.
         }
 
-        $this->removeWaiting($uri, \spl_object_id($deferred)); // DeferredFuture no longer needed for this request.
-
         \assert($connection instanceof Connection);
 
         $stream = $this->getStreamFromConnection($connection, $request);
diff --git a/src/Connection/Http1Connection.php b/src/Connection/Http1Connection.php
index 19a0b76d..c233b0b3 100644
--- a/src/Connection/Http1Connection.php
+++ b/src/Connection/Http1Connection.php
@@ -468,7 +468,11 @@ private function readResponse(
                         $this->priorTimeout = $priorTimeout ?? $this->priorTimeout;
 
                         if ($requestTimeout > 0 && $parser->getState() !== Http1Parser::BODY_IDENTITY_EOF) {
-                            $this->timeoutWatcher = EventLoop::delay($requestTimeout, $this->close(...));
+                            $connectionRef = \WeakReference::create($this);
+                            $this->timeoutWatcher = EventLoop::delay(
+                                $requestTimeout,
+                                static fn () => $connectionRef->get()?->close(),
+                            );
                             EventLoop::unreference($this->timeoutWatcher);
                             $this->watchIdleConnection();
                         } else {
@@ -736,16 +740,19 @@ private function watchIdleConnection(): void
             $this->socket->unreference();
         }
 
-        $this->idleRead = async(function (): ?string {
+        $socket = $this->socket;
+        $connectionRef = \WeakReference::create($this);
+
+        $this->idleRead = async(static function () use ($socket, $connectionRef): ?string {
             $chunk = null;
             try {
-                $chunk = $this->socket?->read();
+                $chunk = $socket?->read();
             } catch (\Throwable) {
                 // Close connection below.
             }
 
             if ($chunk === null) {
-                $this->close();
+                $connectionRef->get()?->close();
             }
 
             return $chunk;
diff --git a/test/Connection/ConnectionLimitingPoolTest.php b/test/Connection/ConnectionLimitingPoolTest.php
index e8570fb1..9a119e79 100644
--- a/test/Connection/ConnectionLimitingPoolTest.php
+++ b/test/Connection/ConnectionLimitingPoolTest.php
@@ -7,6 +7,7 @@
 use Amp\Http\Client\HttpClientBuilder;
 use Amp\Http\Client\Request;
 use Amp\Http\Client\Response;
+use Amp\Http\Client\SocketException;
 use Amp\Http\Client\Trailers;
 use Amp\PHPUnit\AsyncTestCase;
 use Amp\Socket\InternetAddress;
@@ -195,6 +196,34 @@ public function testConnectionNotClosedWhileInUse(): void
         }
     }
 
+    public function testWaitingRequestRemovedIfConnectionAttemptFails(): void
+    {
+        $factory = $this->createMock(ConnectionFactory::class);
+        $factory->expects(self::once())
+            ->method('create')
+            ->willThrowException(new SocketException('Connection failed'));
+
+        $pool = ConnectionLimitingPool::byAuthority(1, $factory);
+
+        $client = (new HttpClientBuilder)
+            ->retry(0)
+            ->usingPool($pool)
+            ->build();
+
+        try {
+            $client->request(new Request('http://localhost'));
+            self::fail('Connection attempt should have failed');
+        } catch (SocketException) {
+            // Expected.
+        }
+
+        delay(0);
+
+        $property = new \ReflectionProperty($pool, 'waiting');
+
+        self::assertSame([], $property->getValue($pool));
+    }
+
     private function createMockConnection(Request $request): Connection&MockObject
     {
         $response = new Response('1.1', 200, null, [], new ReadableBuffer, $request, Future::complete(new Trailers([])));
diff --git a/test/Connection/Http1ConnectionTest.php b/test/Connection/Http1ConnectionTest.php
index 278e3eeb..c6fb721b 100644
--- a/test/Connection/Http1ConnectionTest.php
+++ b/test/Connection/Http1ConnectionTest.php
@@ -80,6 +80,33 @@ public function testConnectionNotBusyWithoutRequestGarbageCollected(): void
         self::assertNotNull($connection->getStream($secondRequest));
     }
 
+    public function testIdleKeepAliveConnectionCanBeGarbageCollected(): void
+    {
+        [$server, $client] = Socket\createSocketPair();
+
+        $connection = new Http1Connection($client, 0, null, 5);
+        $connectionRef = \WeakReference::create($connection);
+
+        $request = new Request('http://localhost');
+        events()->requestStart($request);
+
+        $stream = $connection->getStream($request);
+        $server->write("HTTP/1.1 204 No Content\r\nConnection: keep-alive\r\nContent-Length: 0\r\n\r\n");
+
+        $response = $stream->request($request, new NullCancellation);
+        $response->getBody()->buffer();
+
+        unset($client, $connection, $request, $response, $stream);
+
+        do {
+            delay(0);
+        } while (\gc_collect_cycles());
+
+        self::assertNull($connectionRef->get());
+
+        $server->close();
+    }
+
     public function test100Continue(): void
     {
         [$server, $client] = Socket\createSocketPair();