diff --git a/packages/custom_lint/lib/src/v2/custom_lint_analyzer_plugin.dart b/packages/custom_lint/lib/src/v2/custom_lint_analyzer_plugin.dart
index 42497c9f..b5912747 100644
--- a/packages/custom_lint/lib/src/v2/custom_lint_analyzer_plugin.dart
+++ b/packages/custom_lint/lib/src/v2/custom_lint_analyzer_plugin.dart
@@ -11,6 +11,7 @@ import 'package:analyzer_plugin/src/protocol/protocol_internal.dart'
     show ResponseResult;
 import 'package:async/async.dart';
 import 'package:custom_lint_core/custom_lint_core.dart';
+import 'package:meta/meta.dart';
 import 'package:package_config/package_config.dart';
 import 'package:path/path.dart' as p;
 import 'package:pub_semver/pub_semver.dart';
@@ -114,6 +115,11 @@ class CustomLintServer {
   /// Whether plugins should include lints used for debugging.
   final bool includeBuiltInLints;
 
+  /// Allow mocking a SocketCustomLintServerToClientChannel for test
+  @visibleForTesting
+  Future<SocketCustomLintServerToClientChannel?> get clientChannel =>
+      _clientChannel.safeFirst;
+
   late final StreamSubscription<void> _requestSubscription;
   StreamSubscription<void>? _clientChannelEventsSubscription;
   late PluginVersionCheckParams _pluginVersionCheckParams;
@@ -122,6 +128,7 @@ class CustomLintServer {
       BehaviorSubject<SocketCustomLintServerToClientChannel?>();
   final _contextRoots = BehaviorSubject<AnalysisSetContextRootsParams>();
   final _runner = PendingOperation();
+  final _delayedRequest = <Request>[];
 
   /// A shorthand for accessing the current list of context roots.
   Future<List<ContextRoot>?> get _allContextRoots {
@@ -186,7 +193,10 @@ class CustomLintServer {
         orElse: () async {
           return _runner.run(() async {
             final clientChannel = await _clientChannel.safeFirst;
-            if (clientChannel == null) return null;
+            if (clientChannel == null || !clientChannel.initialized) {
+              _delayedRequest.add(request);
+              return null;
+            }
 
             final response =
                 await clientChannel.sendAnalyzerPluginRequest(request);
@@ -291,6 +301,7 @@ class CustomLintServer {
     return _closeFuture = Future(() async {
       // Cancel pending operations
       await _contextRoots.close();
+      _delayedRequest.clear();
 
       // Flushes logs before stopping server.
       await _runner.wait();
@@ -396,6 +407,14 @@ class CustomLintServer {
     await clientChannel.init(
       debug: configs.any((e) => e != null && e.debug),
     );
+    _sendDelayedRequest();
+  }
+
+  void _sendDelayedRequest() {
+    for (final request in _delayedRequest) {
+      unawaited(_handleRequest(request));
+    }
+    _delayedRequest.clear();
   }
 
   Future<void> _handleEvent(CustomLintEvent event) => _runner.run(() async {
diff --git a/packages/custom_lint/lib/src/v2/server_to_client_channel.dart b/packages/custom_lint/lib/src/v2/server_to_client_channel.dart
index 769655c9..2163bb86 100644
--- a/packages/custom_lint/lib/src/v2/server_to_client_channel.dart
+++ b/packages/custom_lint/lib/src/v2/server_to_client_channel.dart
@@ -4,6 +4,7 @@ import 'dart:io';
 
 import 'package:analyzer_plugin/protocol/protocol.dart';
 import 'package:analyzer_plugin/protocol/protocol_generated.dart';
+import 'package:meta/meta.dart';
 import 'package:path/path.dart';
 import 'package:uuid/uuid.dart';
 
@@ -81,6 +82,16 @@ class SocketCustomLintServerToClientChannel {
   final CustomLintWorkspace _workspace;
 
   AnalysisSetContextRootsParams _contextRoots;
+  bool _initialized = false;
+
+  /// List request before initialized
+  @visibleForTesting
+  List<Request> initialRequest = [];
+
+  /// Initial state
+  ///
+  /// Returns `true` if requested `analysis.setContextRoots`
+  bool get initialized => _initialized;
 
   late final Stream<CustomLintMessage> _messages = _channel.messages
       .map((e) => e! as Map<String, Object?>)
@@ -127,6 +138,7 @@ class SocketCustomLintServerToClientChannel {
       sendAnalyzerPluginRequest(_version.toRequest(const Uuid().v4())),
       sendAnalyzerPluginRequest(_contextRoots.toRequest(const Uuid().v4())),
     ]);
+    _initialized = true;
   }
 
   /// Updates the context roots on the client
@@ -231,6 +243,7 @@ void main(List<String> args) async {
   /// Sends a request based on the analyzer_plugin protocol, expecting
   /// an analyzer_plugin response.
   Future<Response> sendAnalyzerPluginRequest(Request request) async {
+    if (!_initialized) initialRequest.add(request);
     final response = await sendCustomLintRequest(
       CustomLintRequest.analyzerPluginRequest(request, id: request.id),
     );
diff --git a/packages/custom_lint/test/run_plugin.dart b/packages/custom_lint/test/run_plugin.dart
index b9382ea4..eb3c574b 100644
--- a/packages/custom_lint/test/run_plugin.dart
+++ b/packages/custom_lint/test/run_plugin.dart
@@ -20,10 +20,11 @@ Future<List<AnalysisErrorsParams>> runServerInCliModeForApp(
 }
 
 class ManualRunner {
-  ManualRunner(this.runner, this.channel);
+  ManualRunner(this.runner, this.channel, this.server);
 
   final CustomLintRunner runner;
   final ServerIsolateChannel channel;
+  final CustomLintServer server;
 
   Future<void> get initialize => runner.initialize;
 
@@ -91,7 +92,7 @@ Future<ManualRunner> startRunnerForApp(
 
     unawaited(runner.initialize);
 
-    return ManualRunner(runner, channel);
+    return ManualRunner(runner, channel, customLintServer);
   });
 }
 
diff --git a/packages/custom_lint/test/server_test.dart b/packages/custom_lint/test/server_test.dart
index 41ef8515..f7b04821 100644
--- a/packages/custom_lint/test/server_test.dart
+++ b/packages/custom_lint/test/server_test.dart
@@ -71,6 +71,44 @@ void fn() {}
     );
   });
 
+  test('Handles request before server initialized', () async {
+    final plugin = createPlugin(name: 'test_lint', main: helloWordPluginSource);
+
+    final app = createLintUsage(
+      source: {
+        'lib/main.dart': '''
+void fn() {}
+
+void fn2() {}
+''',
+        'lib/another.dart': 'void fn() {}\n',
+      },
+      plugins: {'test_lint': plugin.uri},
+      name: 'test_app',
+    );
+
+    final runner = await startRunnerForApp(app, includeBuiltInLints: false);
+    final another = File(join(app.path, 'lib', 'another.dart'));
+    another.writeAsStringSync('test');
+    await runner.channel.sendRequest(
+      AnalysisUpdateContentParams({
+        another.path: AddContentOverlay(another.readAsStringSync()),
+      }),
+    );
+    await runner.initialize;
+
+    final initialRequest = (await runner.server.clientChannel)?.initialRequest;
+    // Request send before `SocketCustomLintServerToClientChannel.init` must delay,
+    // for ensure initialRequest is [PluginVersionCheckParams, AnalysisSetContextRootsParams]
+    expect(initialRequest, hasLength(2));
+    expect(
+      initialRequest?.last.method,
+      AnalysisSetContextRootsParams([]).toRequest('test').method,
+    );
+
+    await runner.close();
+  });
+
   test('Handles files getting deleted', () async {
     // Regression test for https://github.com/invertase/dart_custom_lint/issues/105
     final plugin = createPlugin(name: 'test_lint', main: helloWordPluginSource);