diff --git a/sdk/lib/_internal/vm/bin/socket_patch.dart b/sdk/lib/_internal/vm/bin/socket_patch.dart
index 6c762bf99528..18c3c86cd167 100644
--- a/sdk/lib/_internal/vm/bin/socket_patch.dart
+++ b/sdk/lib/_internal/vm/bin/socket_patch.dart
@@ -1623,21 +1623,29 @@ base class _NativeSocket extends _NativeSocketNativeWrapper
     void issue() {
       readEventIssued = false;
       if (isClosing) return;
+      // Note: it is by design that we don't deliver closedRead event
+      // unless read events are enabled. This also means we will not
+      // fully close (and dispose) of the socket unless it is drained
+      // of accumulated incomming data.
       if (!sendReadEvents) return;
       if (stopRead()) {
         if (isClosedRead && !closedReadEventSent) {
           if (isClosedWrite) close();
+
           var handler = closedEventHandler;
           if (handler == null) return;
+
           closedReadEventSent = true;
           handler();
         }
         return;
       }
+
       var handler = readEventHandler;
       if (handler == null) return;
-      readEventIssued = true;
       handler();
+
+      readEventIssued = true;
       scheduleMicrotask(issue);
     }
 
@@ -1846,6 +1854,9 @@ base class _NativeSocket extends _NativeSocketNativeWrapper
         sendToEventHandler(1 << shutdownReadCommand);
       }
       isClosedRead = true;
+      // Make sure to dispatch a closedRead event. Shutdown is only complete
+      // once the socket is drained of data and readClosed is dispatched.
+      issueReadEvent();
     }
   }
 
diff --git a/sdk/lib/io/socket.dart b/sdk/lib/io/socket.dart
index 506117e7950e..d988b323c43e 100644
--- a/sdk/lib/io/socket.dart
+++ b/sdk/lib/io/socket.dart
@@ -619,7 +619,12 @@ final class ConnectionTask<S> {
 /// ([RawSocketEvent.closed]).
 abstract interface class RawSocket implements Stream<RawSocketEvent> {
   /// Set or get, if the [RawSocket] should listen for [RawSocketEvent.read]
-  /// events. Default is `true`.
+  /// and [RawSocketEvent.readClosed] events. Default is `true`.
+  ///
+  /// Warning: setting [readEventsEnabled] to `false` might prevent socket
+  /// from fully closing when [SocketDirection.receive] and
+  /// [SocketDirection.send] directions are shutdown independently. See
+  /// [shutdown] for more details.
   abstract bool readEventsEnabled;
 
   /// Set or get, if the [RawSocket] should listen for [RawSocketEvent.write]
@@ -636,8 +641,8 @@ abstract interface class RawSocket implements Stream<RawSocketEvent> {
   /// The [host] can either be a [String] or an [InternetAddress]. If [host] is a
   /// [String], [connect] will perform a [InternetAddress.lookup] and try
   /// all returned [InternetAddress]es, until connected. If IPv4 and IPv6
-  /// addresses are both availble then connections over IPv4 are preferred. If
-  /// no connection can be establed then the error from the first failing
+  /// addresses are both available then connections over IPv4 are preferred. If
+  /// no connection can be established then the error from the first failing
   /// connection is returned.
   ///
   /// The argument [sourceAddress] can be used to specify the local
@@ -788,6 +793,17 @@ abstract interface class RawSocket implements Stream<RawSocketEvent> {
   /// and calling it several times is supported. Calling
   /// shutdown with either [SocketDirection.both] or [SocketDirection.receive]
   /// can result in a [RawSocketEvent.readClosed] event.
+  ///
+  /// Warning: [SocketDirection.receive] direction is only considered to be
+  /// to be fully shutdown once all available data is drained and
+  /// [RawSocketEvent.readClosed] is dispatched. Shutting down
+  /// [SocketDirection.receive] and [SocketDirection.send] directions separately
+  /// without draining the data will lead to socket staying around until the
+  /// data is drained. This can happen if [readEventsEnabled] is set
+  /// to `false` or if received data is not [read] in response to these
+  /// events. This does not apply to shutting down both directions
+  /// simultaneously using [SocketDirection.both] which will discard all
+  /// received data instead.
   void shutdown(SocketDirection direction);
 
   /// Customize the [RawSocket].
diff --git a/tests/standalone/io/issue_22636_test.dart b/tests/standalone/io/issue_22636_test.dart
index 85682d79314d..4cfcac479682 100644
--- a/tests/standalone/io/issue_22636_test.dart
+++ b/tests/standalone/io/issue_22636_test.dart
@@ -8,7 +8,9 @@
 
 import "dart:async";
 import "dart:io";
+
 import "package:expect/expect.dart";
+import "package:expect/async_helper.dart";
 
 final Duration delay = new Duration(milliseconds: 100);
 final List<int> data = new List.generate(100, (i) => i % 20 + 65);
@@ -28,10 +30,11 @@ void serverListen(RawSocket serverSide) {
             serverSide.writeEventsEnabled = true;
           });
         } else {
-          new Future.delayed(delay, () {
+          new Future.delayed(delay, () async {
             Expect.isTrue(serverReadClosedReceived);
             serverSide.shutdown(SocketDirection.send);
-            server.close();
+            await server.close();
+            asyncEnd();
           });
         }
         break;
@@ -58,5 +61,6 @@ Future test() async {
 }
 
 void main() {
+  asyncStart();
   test();
 }
diff --git a/tests/standalone/io/issue_27414_test.dart b/tests/standalone/io/issue_27414_test.dart
new file mode 100644
index 000000000000..31c6558d2047
--- /dev/null
+++ b/tests/standalone/io/issue_27414_test.dart
@@ -0,0 +1,74 @@
+// Copyright (c) 2024, the Dart project authors.  Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+//
+// This test verifies that shuting down receive and send directions separately
+// on a socket correctly shuts the socket down instead of leaking it.
+
+import 'dart:async';
+import 'dart:convert';
+import 'dart:io';
+
+import 'package:expect/expect.dart';
+import 'package:expect/async_helper.dart';
+
+const messageContent = "hello, from the client!";
+late RawServerSocket server;
+late StreamSubscription clientSubscription;
+
+void handleConnection(RawSocket serverSide) {
+  var readClosedReceived = false;
+
+  void serveData(RawSocketEvent event) async {
+    switch (event) {
+      case RawSocketEvent.read:
+        final data = serverSide.read();
+        Expect.equals(messageContent, utf8.decode(data!));
+
+        // There might be a read event in flight, wait for microtasks to drain
+        // and then shutdown read and write directions separately. This
+        // should cause [readClosed] to be dispatched.
+        Future.delayed(Duration(milliseconds: 0), () {
+          serverSide.shutdown(SocketDirection.receive);
+          serverSide.shutdown(SocketDirection.send);
+        });
+        break;
+
+      case RawSocketEvent.readClosed:
+        Expect.isFalse(readClosedReceived);
+        readClosedReceived = true;
+        break;
+
+      case RawSocketEvent.closed:
+        Expect.isTrue(readClosedReceived);
+        await clientSubscription.cancel();
+        await server.close();
+        asyncEnd();
+        break;
+    }
+  }
+
+  serverSide.listen(serveData);
+}
+
+Future test() async {
+  server = await RawServerSocket.bind(InternetAddress.loopbackIPv4, 0);
+  server.listen(handleConnection);
+
+  final client = await RawSocket.connect(
+    InternetAddress.loopbackIPv4,
+    server.port,
+  );
+  clientSubscription = client.listen((RawSocketEvent event) {
+    switch (event) {
+      case RawSocketEvent.write:
+        client.write(utf8.encode(messageContent));
+        break;
+    }
+  });
+}
+
+void main() {
+  asyncStart();
+  test();
+}