diff --git a/pkgs/unified_analytics/CHANGELOG.md b/pkgs/unified_analytics/CHANGELOG.md
index c89094b814..1c827f0a78 100644
--- a/pkgs/unified_analytics/CHANGELOG.md
+++ b/pkgs/unified_analytics/CHANGELOG.md
@@ -1,3 +1,10 @@
+## 6.0.0-wip
+
+- Consolidate `Session` functionality into `UserProperty` to prevent race condition crash where session logic crashed before initializing `UserProperty`
+- Get rid of `late` variables throughout implementation class, `AnalyticsImpl`
+- Any error events (`Event.analyticsException`) encountered within package will be sent when invoking `Analytics.close`; replacing `ErrorHandler` functionality
+- Exposing new method for `FakeAnalytics.sendPendingErrorEvents` to send error events on command
+
 ## 5.8.8
 
 - [Bug fix](https://github.com/dart-lang/tools/issues/252) rewrite the other call site for the session file
@@ -8,7 +15,7 @@
 
 ## 5.8.6
 
-- Refactored session handler class to use the last modified timestamp as the last ping value
+- Refactored session handler class to use the last modified timestamp as the last ping value to prevent writing to file with each send
 - Bumping intl package to 0.19.0 to fix version solving issue with flutter_tools
 
 ## 5.8.5
diff --git a/pkgs/unified_analytics/example/serving_surveys.dart b/pkgs/unified_analytics/example/serving_surveys.dart
index 18631b32aa..e433f9026a 100644
--- a/pkgs/unified_analytics/example/serving_surveys.dart
+++ b/pkgs/unified_analytics/example/serving_surveys.dart
@@ -5,6 +5,7 @@
 import 'package:clock/clock.dart';
 import 'package:file/file.dart';
 import 'package:file/memory.dart';
+import 'package:path/path.dart' as p;
 
 import 'package:unified_analytics/src/constants.dart';
 import 'package:unified_analytics/src/enums.dart';
@@ -57,8 +58,11 @@ void main() async {
         fs: fs,
         platform: DevicePlatform.macos,
         surveyHandler: FakeSurveyHandler.fromList(
-          homeDirectory: home,
-          fs: fs,
+          dismissedSurveyFile: fs.file(p.join(
+            home.path,
+            kDartToolDirectoryName,
+            kDismissedSurveyFileName,
+          )),
           initializedSurveys: [
             Survey(
               uniqueId: 'uniqueId',
diff --git a/pkgs/unified_analytics/lib/src/analytics.dart b/pkgs/unified_analytics/lib/src/analytics.dart
index 9187d02a52..da3fe0973b 100644
--- a/pkgs/unified_analytics/lib/src/analytics.dart
+++ b/pkgs/unified_analytics/lib/src/analytics.dart
@@ -16,19 +16,14 @@ import 'asserts.dart';
 import 'config_handler.dart';
 import 'constants.dart';
 import 'enums.dart';
-import 'error_handler.dart';
 import 'event.dart';
 import 'ga_client.dart';
 import 'initializer.dart';
 import 'log_handler.dart';
-import 'session.dart';
 import 'survey_handler.dart';
 import 'user_property.dart';
 import 'utils.dart';
 
-/// For passing the [Analytics.send] method to classes created by [Analytics].
-typedef SendFunction = void Function(Event event);
-
 abstract class Analytics {
   /// The default factory constructor that will return an implementation
   /// of the [Analytics] abstract class using the [LocalFileSystem].
@@ -84,6 +79,8 @@ abstract class Analytics {
       apiSecret: kGoogleAnalyticsApiSecret,
     );
 
+    final firstRun = runInitialization(homeDirectory: homeDirectory, fs: fs);
+
     return AnalyticsImpl(
       tool: tool,
       homeDirectory: homeDirectory,
@@ -94,10 +91,17 @@ abstract class Analytics {
       toolsMessageVersion: kToolsMessageVersion,
       fs: fs,
       gaClient: gaClient,
-      surveyHandler: SurveyHandler(homeDirectory: homeDirectory, fs: fs),
+      surveyHandler: SurveyHandler(
+        dismissedSurveyFile: fs.file(p.join(
+          homeDirectory.path,
+          kDartToolDirectoryName,
+          kDismissedSurveyFileName,
+        )),
+      ),
       enableAsserts: enableAsserts,
       clientIde: clientIde,
       enabledFeatures: enabledFeatures,
+      firstRun: firstRun,
     );
   }
 
@@ -154,6 +158,8 @@ abstract class Analytics {
       apiSecret: kTestApiSecret,
     );
 
+    final firstRun = runInitialization(homeDirectory: homeDirectory, fs: fs);
+
     return AnalyticsImpl(
       tool: tool,
       homeDirectory: homeDirectory,
@@ -164,10 +170,17 @@ abstract class Analytics {
       toolsMessageVersion: kToolsMessageVersion,
       fs: fs,
       gaClient: gaClient,
-      surveyHandler: SurveyHandler(homeDirectory: homeDirectory, fs: fs),
+      surveyHandler: SurveyHandler(
+        dismissedSurveyFile: fs.file(p.join(
+          homeDirectory.path,
+          kDartToolDirectoryName,
+          kDismissedSurveyFileName,
+        )),
+      ),
       enableAsserts: enableAsserts,
       clientIde: clientIde,
       enabledFeatures: enabledFeatures,
+      firstRun: firstRun,
     );
   }
 
@@ -190,26 +203,33 @@ abstract class Analytics {
     GAClient? gaClient,
     int toolsMessageVersion = kToolsMessageVersion,
     String toolsMessage = kToolsMessage,
-  }) =>
-      FakeAnalytics(
-        tool: tool,
-        homeDirectory: homeDirectory,
-        flutterChannel: flutterChannel,
-        toolsMessageVersion: toolsMessageVersion,
-        flutterVersion: flutterVersion,
-        dartVersion: dartVersion,
-        platform: platform,
-        fs: fs,
-        surveyHandler: surveyHandler ??
-            FakeSurveyHandler.fromList(
-              homeDirectory: homeDirectory,
-              fs: fs,
-              initializedSurveys: [],
-            ),
-        gaClient: gaClient ?? const FakeGAClient(),
-        clientIde: clientIde,
-        enabledFeatures: enabledFeatures,
-      );
+  }) {
+    final firstRun = runInitialization(homeDirectory: homeDirectory, fs: fs);
+
+    return FakeAnalytics(
+      tool: tool,
+      homeDirectory: homeDirectory,
+      flutterChannel: flutterChannel,
+      toolsMessageVersion: toolsMessageVersion,
+      flutterVersion: flutterVersion,
+      dartVersion: dartVersion,
+      platform: platform,
+      fs: fs,
+      surveyHandler: surveyHandler ??
+          FakeSurveyHandler.fromList(
+            dismissedSurveyFile: fs.file(p.join(
+              homeDirectory.path,
+              kDartToolDirectoryName,
+              kDismissedSurveyFileName,
+            )),
+            initializedSurveys: [],
+          ),
+      gaClient: gaClient ?? const FakeGAClient(),
+      clientIde: clientIde,
+      enabledFeatures: enabledFeatures,
+      firstRun: firstRun,
+    );
+  }
 
   /// The shared identifier for Flutter and Dart related tooling using
   /// package:unified_analytics.
@@ -320,22 +340,19 @@ abstract class Analytics {
 class AnalyticsImpl implements Analytics {
   final DashTool tool;
   final FileSystem fs;
-  late final ConfigHandler _configHandler;
+  final int toolsMessageVersion;
+  final ConfigHandler _configHandler;
   final GAClient _gaClient;
   final SurveyHandler _surveyHandler;
-  late String _clientId;
-  late final File _clientIdFile;
-  late final UserProperty userProperty;
-  late final LogHandler _logHandler;
-  late final Session _sessionHandler;
-  late final ErrorHandler _errorHandler;
-  final int toolsMessageVersion;
+  final File _clientIdFile;
+  final UserProperty _userProperty;
+  final LogHandler _logHandler;
 
   /// Tells the client if they need to show a message to the
   /// user; this will return true if it is the first time the
   /// package is being used for a developer or if the consent
   /// message has been updated by the package.
-  late bool _showMessage;
+  bool _showMessage = false;
 
   /// When set to `true`, various assert statements will be enabled
   /// to ensure usage of this class is within GA4 limitations.
@@ -351,6 +368,16 @@ class AnalyticsImpl implements Analytics {
   /// from the [GAClient].
   final _futures = <Future<Response>>[];
 
+  /// Internal value for the client id which will be lazily loaded.
+  String? _clientId;
+
+  /// Internal collection of [Event]s that have been sent
+  /// for errors encountered within package:unified_analytics.
+  ///
+  /// Stores each of the events that have been sent to GA4 so that the
+  /// same error doesn't get sent twice.
+  final Set<Event> _sentErrorEvents = {};
+
   AnalyticsImpl({
     required this.tool,
     required Directory homeDirectory,
@@ -365,9 +392,50 @@ class AnalyticsImpl implements Analytics {
     required GAClient gaClient,
     required SurveyHandler surveyHandler,
     required bool enableAsserts,
+    required bool firstRun,
   })  : _gaClient = gaClient,
         _surveyHandler = surveyHandler,
-        _enableAsserts = enableAsserts {
+        _enableAsserts = enableAsserts,
+        _clientIdFile = fs.file(p.join(
+          homeDirectory.path,
+          kDartToolDirectoryName,
+          kClientIdFileName,
+        )),
+        _userProperty = UserProperty(
+          sessionFile: fs.file(p.join(
+            homeDirectory.path,
+            kDartToolDirectoryName,
+            kSessionFileName,
+          )),
+          flutterChannel: flutterChannel,
+          host: platform.label,
+          flutterVersion: flutterVersion,
+          dartVersion: dartVersion,
+          tool: tool.label,
+          // We truncate this to a maximum of 36 characters since this can
+          // a very long string for some operating systems
+          hostOsVersion:
+              truncateStringToLength(io.Platform.operatingSystemVersion, 36),
+          locale: io.Platform.localeName,
+          clientIde: clientIde,
+          enabledFeatures: enabledFeatures,
+        ),
+        _configHandler = ConfigHandler(
+          fs: fs,
+          homeDirectory: homeDirectory,
+          configFile: fs.file(p.join(
+            homeDirectory.path,
+            kDartToolDirectoryName,
+            kConfigFileName,
+          )),
+        ),
+        _logHandler = LogHandler(
+          logFile: fs.file(p.join(
+            homeDirectory.path,
+            kDartToolDirectoryName,
+            kLogFileName,
+          )),
+        ) {
     // Initialize date formatting for `package:intl` within constructor
     // so clients using this package won't need to
     initializeDateFormatting();
@@ -375,14 +443,7 @@ class AnalyticsImpl implements Analytics {
     // This initializer class will let the instance know
     // if it was the first run; if it is, nothing will be sent
     // on the first run
-    final initializer = Initializer(
-      fs: fs,
-      tool: tool.label,
-      homeDirectory: homeDirectory,
-      toolsMessageVersion: toolsMessageVersion,
-    );
-    initializer.run();
-    if (initializer.firstRun) {
+    if (firstRun) {
       _showMessage = true;
       _firstRun = true;
     } else {
@@ -390,13 +451,6 @@ class AnalyticsImpl implements Analytics {
       _firstRun = false;
     }
 
-    // Create the config handler that will parse the config file
-    _configHandler = ConfigHandler(
-      fs: fs,
-      homeDirectory: homeDirectory,
-      initializer: initializer,
-    );
-
     // Check if the tool has already been onboarded, and if it
     // has, check if the latest message version is greater to
     // prompt the client to show a message
@@ -413,54 +467,17 @@ class AnalyticsImpl implements Analytics {
       // will be blocked
       _firstRun = true;
     }
-
-    _clientIdFile = fs.file(
-        p.join(homeDirectory.path, kDartToolDirectoryName, kClientIdFileName));
-    _clientId = _clientIdFile.readAsStringSync();
-
-    // Initialization for the error handling class that will prevent duplicate
-    // [Event.analyticsException] events from being sent to GA4
-    _errorHandler = ErrorHandler(sendFunction: send);
-
-    // Initialize the user property class that will be attached to
-    // each event that is sent to Google Analytics -- it will be responsible
-    // for getting the session id or rolling the session if the duration
-    // exceeds [kSessionDurationMinutes]
-    _sessionHandler = Session(
-      homeDirectory: homeDirectory,
-      fs: fs,
-      errorHandler: _errorHandler,
-    );
-    userProperty = UserProperty(
-      session: _sessionHandler,
-      flutterChannel: flutterChannel,
-      host: platform.label,
-      flutterVersion: flutterVersion,
-      dartVersion: dartVersion,
-      tool: tool.label,
-      // We truncate this to a maximum of 36 characters since this can
-      // a very long string for some operating systems
-      hostOsVersion:
-          truncateStringToLength(io.Platform.operatingSystemVersion, 36),
-      locale: io.Platform.localeName,
-      clientIde: clientIde,
-      enabledFeatures: enabledFeatures,
-    );
-
-    // Initialize the log handler to persist events that are being sent
-    _logHandler = LogHandler(
-      fs: fs,
-      homeDirectory: homeDirectory,
-      errorHandler: _errorHandler,
-    );
-
-    // Initialize the session handler with the session_id
-    // by parsing the json file
-    _sessionHandler.initialize(telemetryEnabled);
   }
 
   @override
-  String get clientId => _clientId;
+  String get clientId {
+    if (!_clientIdFile.existsSync()) {
+      createClientIdFile(clientIdFile: _clientIdFile);
+    }
+    _clientId ??= _clientIdFile.readAsStringSync();
+
+    return _clientId!;
+  }
 
   @override
   String get getConsentMessage {
@@ -503,7 +520,7 @@ class AnalyticsImpl implements Analytics {
 
   @override
   Map<String, Map<String, Object?>> get userPropertyMap =>
-      userProperty.preparePayload();
+      _userProperty.preparePayload();
 
   @override
   void clientShowedMessage() {
@@ -529,6 +546,9 @@ class AnalyticsImpl implements Analytics {
 
   @override
   Future<void> close({int delayDuration = kDelayDuration}) async {
+    // Collect any errors encountered and send
+    _sendPendingErrorEvents();
+
     await Future.wait(_futures).timeout(
       Duration(milliseconds: delayDuration),
       onTimeout: () => [],
@@ -555,7 +575,7 @@ class AnalyticsImpl implements Analytics {
       // Apply the survey's sample rate; if the generated value from
       // the client id and survey's uniqueId are less, it will not get
       // sent to the user
-      if (survey.samplingRate < sampleRate(_clientId, survey.uniqueId)) {
+      if (survey.samplingRate < sampleRate(clientId, survey.uniqueId)) {
         continue;
       }
 
@@ -610,10 +630,10 @@ class AnalyticsImpl implements Analytics {
 
     // Construct the body of the request
     final body = generateRequestBody(
-      clientId: _clientId,
+      clientId: clientId,
       eventName: event.eventName,
       eventData: event.eventData,
-      userProperty: userProperty,
+      userProperty: _userProperty,
     );
 
     if (_enableAsserts) checkBody(body);
@@ -640,8 +660,8 @@ class AnalyticsImpl implements Analytics {
       // Recreate the session and client id file; no need to
       // recreate the log file since it will only receives events
       // to persist from events sent
-      Initializer.createClientIdFile(clientIdFile: _clientIdFile);
-      Initializer.createSessionFile(sessionFile: _sessionHandler.sessionFile);
+      createClientIdFile(clientIdFile: _clientIdFile);
+      createSessionFile(sessionFile: _userProperty.sessionFile);
 
       // Reread the client ID string so an empty string is not being
       // sent to GA4 since the persisted files are cleared when a user
@@ -651,10 +671,10 @@ class AnalyticsImpl implements Analytics {
       // We must construct the body at this point after we have read in the
       // new client id string that was generated
       body = generateRequestBody(
-        clientId: _clientId,
+        clientId: clientId,
         eventName: collectionEvent.eventName,
         eventData: collectionEvent.eventData,
-        userProperty: userProperty,
+        userProperty: _userProperty,
       );
 
       _logHandler.save(data: body);
@@ -662,18 +682,18 @@ class AnalyticsImpl implements Analytics {
       // Construct the body of the request to signal
       // telemetry status toggling
       body = generateRequestBody(
-        clientId: _clientId,
+        clientId: clientId,
         eventName: collectionEvent.eventName,
         eventData: collectionEvent.eventData,
-        userProperty: userProperty,
+        userProperty: _userProperty,
       );
 
       // For opted out users, data in the persisted files is cleared
-      _sessionHandler.sessionFile.writeAsStringSync('');
+      _userProperty.sessionFile.writeAsStringSync('');
       _logHandler.logFile.writeAsStringSync('');
       _clientIdFile.writeAsStringSync('');
 
-      _clientId = _clientIdFile.readAsStringSync();
+      _clientId = '';
     }
 
     // Pass to the google analytics client to send with a
@@ -706,6 +726,30 @@ class AnalyticsImpl implements Analytics {
     _surveyHandler.dismiss(survey, false);
     send(Event.surveyShown(surveyId: survey.uniqueId));
   }
+
+  /// Send any pending error events, useful for tests to avoid closing
+  /// the connection.
+  ///
+  /// In the main implementation, [AnalyticsImpl], error events are only
+  /// sent on exit when [close] is invoked. This helper method can instead
+  /// have those error events sent immediately to help with tests that check
+  /// [FakeAnalytics.sentEvents].
+  void _sendPendingErrorEvents() {
+    // Collect any errors encountered and send
+    final errorEvents = {..._userProperty.errorSet, ..._logHandler.errorSet};
+    errorEvents
+        .where((event) =>
+            event.eventName == DashEvent.analyticsException &&
+            !_sentErrorEvents.contains(event))
+        .forEach(send);
+
+    // Ensure the same event doesn't get sent again
+    _sentErrorEvents.addAll(errorEvents);
+
+    // Clear error sets
+    _userProperty.errorSet.clear();
+    _logHandler.errorSet.clear();
+  }
 }
 
 /// This fake instance of [Analytics] is intended to be used by clients of
@@ -728,17 +772,18 @@ class FakeAnalytics extends AnalyticsImpl {
     required super.platform,
     required super.fs,
     required super.surveyHandler,
+    required super.firstRun,
     super.flutterChannel,
     super.flutterVersion,
     super.clientIde,
     super.enabledFeatures,
-    int? toolsMessageVersion,
-    GAClient? gaClient,
-  }) : super(
-          gaClient: gaClient ?? const FakeGAClient(),
-          enableAsserts: true,
-          toolsMessageVersion: toolsMessageVersion ?? kToolsMessageVersion,
-        );
+    super.toolsMessageVersion = kToolsMessageVersion,
+    super.gaClient = const FakeGAClient(),
+    super.enableAsserts = true,
+  });
+
+  /// Getter to reference the private [UserProperty].
+  UserProperty get userProperty => _userProperty;
 
   @override
   void send(Event event) {
@@ -746,10 +791,10 @@ class FakeAnalytics extends AnalyticsImpl {
 
     // Construct the body of the request
     final body = generateRequestBody(
-      clientId: _clientId,
+      clientId: clientId,
       eventName: event.eventName,
       eventData: event.eventData,
-      userProperty: userProperty,
+      userProperty: _userProperty,
     );
 
     if (_enableAsserts) checkBody(body);
@@ -760,6 +805,13 @@ class FakeAnalytics extends AnalyticsImpl {
     // for internal methods in the `Analytics` instance
     sentEvents.add(event);
   }
+
+  /// Public instance method to invoke private method that sends any
+  /// pending error events.
+  ///
+  /// If this is never invoked, any pending error events will be sent
+  /// when invoking the [close] method.
+  void sendPendingErrorEvents() => _sendPendingErrorEvents();
 }
 
 /// An implementation that will never send events.
diff --git a/pkgs/unified_analytics/lib/src/config_handler.dart b/pkgs/unified_analytics/lib/src/config_handler.dart
index f9779dfabc..ea6f51ff6c 100644
--- a/pkgs/unified_analytics/lib/src/config_handler.dart
+++ b/pkgs/unified_analytics/lib/src/config_handler.dart
@@ -35,12 +35,11 @@ class ConfigHandler {
 
   final FileSystem fs;
   final Directory homeDirectory;
-  final Initializer initializer;
   final File configFile;
 
   final Map<String, ToolInfo> parsedTools = <String, ToolInfo>{};
 
-  late DateTime configFileLastModified;
+  DateTime configFileLastModified;
 
   /// Reporting enabled unless specified by user
   bool _telemetryEnabled = true;
@@ -48,16 +47,8 @@ class ConfigHandler {
   ConfigHandler({
     required this.fs,
     required this.homeDirectory,
-    required this.initializer,
-  }) : configFile = fs.file(p.join(
-          homeDirectory.path,
-          kDartToolDirectoryName,
-          kConfigFileName,
-        )) {
-    // Get the last time the file was updated and check this
-    // datestamp whenever the client asks for the telemetry enabled boolean
-    configFileLastModified = configFile.lastModifiedSync();
-
+    required this.configFile,
+  }) : configFileLastModified = configFile.lastModifiedSync() {
     // Call the method to parse the contents of the config file when
     // this class is initialized
     parseConfig();
@@ -184,7 +175,15 @@ class ConfigHandler {
   /// This will reset the configuration file and clear the
   /// [parsedTools] map and trigger parsing the config again.
   void resetConfig() {
-    initializer.run(forceReset: true);
+    createConfigFile(
+      configFile: fs.file(p.join(
+        homeDirectory.path,
+        kDartToolDirectoryName,
+        kConfigFileName,
+      )),
+      fs: fs,
+      homeDirectory: homeDirectory,
+    );
     parsedTools.clear();
     parseConfig();
   }
diff --git a/pkgs/unified_analytics/lib/src/constants.dart b/pkgs/unified_analytics/lib/src/constants.dart
index 9dd56812f3..41f7c6ecce 100644
--- a/pkgs/unified_analytics/lib/src/constants.dart
+++ b/pkgs/unified_analytics/lib/src/constants.dart
@@ -82,7 +82,7 @@ const int kLogFileLength = 2500;
 const String kLogFileName = 'dart-flutter-telemetry.log';
 
 /// The current version of the package, should be in line with pubspec version.
-const String kPackageVersion = '5.8.8';
+const String kPackageVersion = '6.0.0-wip';
 
 /// The minimum length for a session.
 const int kSessionDurationMinutes = 30;
diff --git a/pkgs/unified_analytics/lib/src/error_handler.dart b/pkgs/unified_analytics/lib/src/error_handler.dart
deleted file mode 100644
index 5937db93a0..0000000000
--- a/pkgs/unified_analytics/lib/src/error_handler.dart
+++ /dev/null
@@ -1,32 +0,0 @@
-// Copyright (c) 2023, 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.
-
-import 'analytics.dart';
-import 'enums.dart';
-import 'event.dart';
-
-class ErrorHandler {
-  /// Stores each of the events that have been sent to GA4 so that the
-  /// same error doesn't get sent twice.
-  final Set<Event> _sentErrorEvents = {};
-  final SendFunction _sendFunction;
-
-  /// Handles any errors encountered within package:unified_analytics.
-  ErrorHandler({required SendFunction sendFunction})
-      : _sendFunction = sendFunction;
-
-  /// Sends the encountered error [Event.analyticsException] to GA4 backend.
-  ///
-  /// This method will not send the event to GA4 if it has already been
-  /// sent before during the current process.
-  void log(Event event) {
-    if (event.eventName != DashEvent.analyticsException ||
-        _sentErrorEvents.contains(event)) {
-      return;
-    }
-
-    _sendFunction(event);
-    _sentErrorEvents.add(event);
-  }
-}
diff --git a/pkgs/unified_analytics/lib/src/initializer.dart b/pkgs/unified_analytics/lib/src/initializer.dart
index a4d453a69c..650388ba33 100644
--- a/pkgs/unified_analytics/lib/src/initializer.dart
+++ b/pkgs/unified_analytics/lib/src/initializer.dart
@@ -9,133 +9,116 @@ import 'package:path/path.dart' as p;
 import 'constants.dart';
 import 'utils.dart';
 
-class Initializer {
-  final FileSystem fs;
-  final String tool;
-  final Directory homeDirectory;
-  final int toolsMessageVersion;
-  bool firstRun = false;
-
-  /// Responsibe for the initialization of the files
-  /// necessary for analytics reporting.
-  ///
-  /// Creates the configuration file that allows the user to
-  /// mannually opt out of reporting along with the file containing
-  /// the client ID to be used across all relevant tooling.
-  ///
-  /// Updating of the config file with new versions will
-  /// not be handled by the [Initializer].
-  Initializer({
-    required this.fs,
-    required this.tool,
-    required this.homeDirectory,
-    required this.toolsMessageVersion,
-  });
-
-  /// Creates the text file that will contain the client ID
-  /// which will be used across all related tools for analytics
-  /// reporting in GA.
-  static void createClientIdFile({required File clientIdFile}) {
-    clientIdFile.createSync(recursive: true);
-    clientIdFile.writeAsStringSync(Uuid().generateV4());
+/// Creates the text file that will contain the client ID
+/// which will be used across all related tools for analytics
+/// reporting in GA.
+void createClientIdFile({required File clientIdFile}) {
+  clientIdFile.createSync(recursive: true);
+  clientIdFile.writeAsStringSync(Uuid().generateV4());
+}
+
+/// Creates the configuration file with the default message
+/// in the user's home directory.
+void createConfigFile({
+  required File configFile,
+  required Directory homeDirectory,
+  required FileSystem fs,
+}) {
+  configFile.createSync(recursive: true);
+
+  // If the user was previously opted out, then we will
+  // replace the line that assumes automatic opt in with
+  // an opt out from the start
+  if (legacyOptOut(fs: fs, home: homeDirectory)) {
+    configFile.writeAsStringSync(
+        kConfigString.replaceAll('reporting=1', 'reporting=0'));
+  } else {
+    configFile.writeAsStringSync(kConfigString);
   }
+}
+
+/// Creates that file that will persist dismissed survey ids.
+void createDismissedSurveyFile({required File dismissedSurveyFile}) {
+  dismissedSurveyFile.createSync(recursive: true);
+  dismissedSurveyFile.writeAsStringSync('{}');
+}
 
-  /// Creates the configuration file with the default message
-  /// in the user's home directory.
-  void createConfigFile({
-    required File configFile,
-    required String dateStamp,
-    required String tool,
-    required int toolsMessageVersion,
-  }) {
-    configFile.createSync(recursive: true);
-
-    // If the user was previously opted out, then we will
-    // replace the line that assumes automatic opt in with
-    // an opt out from the start
-    if (legacyOptOut(fs: fs, home: homeDirectory)) {
-      configFile.writeAsStringSync(
-          kConfigString.replaceAll('reporting=1', 'reporting=0'));
-    } else {
-      configFile.writeAsStringSync(kConfigString);
-    }
+/// Creates that log file that will store the record formatted
+/// events locally on the user's machine.
+void createLogFile({required File logFile}) {
+  logFile.createSync(recursive: true);
+}
+
+/// Creates the session file which will contain
+/// the current session id which is the current timestamp.
+///
+/// It also returns the timestamp used for the session if it needs
+/// to be accessed.
+DateTime createSessionFile({required File sessionFile}) {
+  final now = clock.now();
+  sessionFile.createSync(recursive: true);
+  writeSessionContents(sessionFile: sessionFile);
+
+  return now;
+}
+
+/// Performs all of the initialization checks for the required files.
+///
+/// Returns `true` if the config file was created indicating it is the first
+/// time this package was run on a user's machine.
+///
+/// Checks for the following:
+/// - Config file
+/// - Client ID file
+/// - Session JSON file
+/// - Log file
+/// - Dismissed survey JSON file
+bool runInitialization({
+  required Directory homeDirectory,
+  required FileSystem fs,
+}) {
+  var firstRun = false;
+
+  // When the config file doesn't exist, initialize it with the default tools
+  // and the current date
+  final configFile = fs.file(
+      p.join(homeDirectory.path, kDartToolDirectoryName, kConfigFileName));
+  if (!configFile.existsSync()) {
+    firstRun = true;
+    createConfigFile(
+      configFile: configFile,
+      fs: fs,
+      homeDirectory: homeDirectory,
+    );
   }
 
-  /// Creates that file that will persist dismissed survey ids.
-  static void createDismissedSurveyFile({required File dismissedSurveyFile}) {
-    dismissedSurveyFile.createSync(recursive: true);
-    dismissedSurveyFile.writeAsStringSync('{}');
+  // Begin initialization checks for the client id
+  final clientFile = fs.file(
+      p.join(homeDirectory.path, kDartToolDirectoryName, kClientIdFileName));
+  if (!clientFile.existsSync()) {
+    createClientIdFile(clientIdFile: clientFile);
   }
 
-  /// Creates that log file that will store the record formatted
-  /// events locally on the user's machine.
-  void createLogFile({required File logFile}) {
-    logFile.createSync(recursive: true);
+  // Begin initialization checks for the session file
+  final sessionFile = fs.file(
+      p.join(homeDirectory.path, kDartToolDirectoryName, kSessionFileName));
+  if (!sessionFile.existsSync()) {
+    createSessionFile(sessionFile: sessionFile);
   }
 
-  /// Creates the session file which will contain
-  /// the current session id which is the current timestamp.
-  ///
-  /// [sessionIdOverride] can be provided as an override, otherwise it
-  /// will use the current timestamp from [Clock.now].
-  static void createSessionFile({
-    required File sessionFile,
-    DateTime? sessionIdOverride,
-  }) {
-    sessionFile.createSync(recursive: true);
-    writeSessionContents(sessionFile: sessionFile);
+  // Begin initialization checks for the log file to persist events locally
+  final logFile =
+      fs.file(p.join(homeDirectory.path, kDartToolDirectoryName, kLogFileName));
+  if (!logFile.existsSync()) {
+    createLogFile(logFile: logFile);
   }
 
-  /// This will check that there is a client ID populated in
-  /// the user's home directory under the dart-tool directory.
-  /// If it doesn't exist, one will be created there.
-  ///
-  /// Passing [forceReset] as true will only reset the configuration
-  /// file, it won't recreate the client id, session, and log files
-  /// if they currently exist on disk.
-  void run({bool forceReset = false}) {
-    // Begin by checking for the config file
-    final configFile = fs.file(
-        p.join(homeDirectory.path, kDartToolDirectoryName, kConfigFileName));
-
-    // When the config file doesn't exist, initialize it with the default tools
-    // and the current date
-    if (!configFile.existsSync() || forceReset) {
-      firstRun = true;
-      createConfigFile(
-        configFile: configFile,
-        dateStamp: dateStamp,
-        tool: tool,
-        toolsMessageVersion: toolsMessageVersion,
-      );
-    }
-
-    // Begin initialization checks for the client id
-    final clientFile = fs.file(
-        p.join(homeDirectory.path, kDartToolDirectoryName, kClientIdFileName));
-    if (!clientFile.existsSync()) {
-      createClientIdFile(clientIdFile: clientFile);
-    }
-
-    // Begin initialization checks for the session file
-    final sessionFile = fs.file(
-        p.join(homeDirectory.path, kDartToolDirectoryName, kSessionFileName));
-    if (!sessionFile.existsSync()) {
-      createSessionFile(sessionFile: sessionFile);
-    }
-
-    // Begin initialization checks for the log file to persist events locally
-    final logFile = fs
-        .file(p.join(homeDirectory.path, kDartToolDirectoryName, kLogFileName));
-    if (!logFile.existsSync()) {
-      createLogFile(logFile: logFile);
-    }
-
-    // Begin initialization checks for the dismissed survey file
-    final dismissedSurveyFile = fs.file(p.join(
-        homeDirectory.path, kDartToolDirectoryName, kDismissedSurveyFileName));
-    if (!dismissedSurveyFile.existsSync()) {
-      createDismissedSurveyFile(dismissedSurveyFile: dismissedSurveyFile);
-    }
+  // Begin initialization checks for the dismissed survey file
+  final dismissedSurveyFile = fs.file(p.join(
+      homeDirectory.path, kDartToolDirectoryName, kDismissedSurveyFileName));
+  if (!dismissedSurveyFile.existsSync()) {
+    createDismissedSurveyFile(dismissedSurveyFile: dismissedSurveyFile);
   }
+
+  return firstRun;
 }
diff --git a/pkgs/unified_analytics/lib/src/log_handler.dart b/pkgs/unified_analytics/lib/src/log_handler.dart
index c406cce944..6a0f058581 100644
--- a/pkgs/unified_analytics/lib/src/log_handler.dart
+++ b/pkgs/unified_analytics/lib/src/log_handler.dart
@@ -6,10 +6,8 @@ import 'dart:convert';
 
 import 'package:clock/clock.dart';
 import 'package:file/file.dart';
-import 'package:path/path.dart' as p;
 
 import 'constants.dart';
-import 'error_handler.dart';
 import 'event.dart';
 import 'initializer.dart';
 
@@ -154,28 +152,20 @@ class LogFileStats {
 }
 
 /// This class is responsible for writing to a log
-/// file that has been initialized by the [Initializer].
+/// file that has been initialized by the [createLogFile].
 ///
 /// It will be treated as an append only log and will be limited
 /// to have has many data records as specified by [kLogFileLength].
 class LogHandler {
-  final FileSystem fs;
-  final Directory homeDirectory;
   final File logFile;
-  final ErrorHandler _errorHandler;
+
+  /// Contains instances of [Event.analyticsException] that were encountered
+  /// during a workflow and will be sent to GA4 for collection.
+  final Set<Event> errorSet = {};
 
   /// A log handler constructor that will delegate saving
   /// logs and retrieving stats from the persisted log.
-  LogHandler({
-    required this.fs,
-    required this.homeDirectory,
-    required ErrorHandler errorHandler,
-  })  : logFile = fs.file(p.join(
-          homeDirectory.path,
-          kDartToolDirectoryName,
-          kLogFileName,
-        )),
-        _errorHandler = errorHandler;
+  LogHandler({required this.logFile});
 
   /// Get stats from the persisted log file.
   ///
@@ -192,7 +182,7 @@ class LogHandler {
           try {
             return LogItem.fromRecord(jsonDecode(e) as Map<String, Object?>);
           } on FormatException catch (err) {
-            _errorHandler.log(Event.analyticsException(
+            errorSet.add(Event.analyticsException(
               workflow: 'LogFileStats.logFileStats',
               error: err.runtimeType.toString(),
               description: 'message: ${err.message}\nsource: ${err.source}',
@@ -201,7 +191,7 @@ class LogHandler {
             return null;
             // ignore: avoid_catching_errors
           } on TypeError catch (err) {
-            _errorHandler.log(Event.analyticsException(
+            errorSet.add(Event.analyticsException(
               workflow: 'LogFileStats.logFileStats',
               error: err.runtimeType.toString(),
             ));
diff --git a/pkgs/unified_analytics/lib/src/session.dart b/pkgs/unified_analytics/lib/src/session.dart
deleted file mode 100644
index 540f1fdbd0..0000000000
--- a/pkgs/unified_analytics/lib/src/session.dart
+++ /dev/null
@@ -1,126 +0,0 @@
-// Copyright (c) 2023, 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.
-
-import 'dart:convert';
-
-import 'package:clock/clock.dart';
-import 'package:file/file.dart';
-import 'package:path/path.dart' as p;
-
-import 'constants.dart';
-import 'error_handler.dart';
-import 'event.dart';
-import 'initializer.dart';
-import 'utils.dart';
-
-class Session {
-  final Directory homeDirectory;
-  final FileSystem fs;
-  final File sessionFile;
-  final ErrorHandler _errorHandler;
-
-  int? _sessionId;
-
-  Session({
-    required this.homeDirectory,
-    required this.fs,
-    required ErrorHandler errorHandler,
-  })  : sessionFile = fs.file(p.join(
-            homeDirectory.path, kDartToolDirectoryName, kSessionFileName)),
-        _errorHandler = errorHandler;
-
-  /// This will use the data parsed from the
-  /// session file in the dart-tool directory
-  /// to get the session id if the last ping was within
-  /// [kSessionDurationMinutes].
-  ///
-  /// If time since last ping exceeds the duration, then the file
-  /// will be updated with a new session id and that will be returned.
-  ///
-  /// Note, the file will always be updated when calling this method
-  /// because the last ping variable will always need to be persisted.
-  int? getSessionId() {
-    _refreshSessionData();
-    final now = clock.now();
-
-    // Convert the epoch time from the last ping into datetime and check if we
-    // are within the kSessionDurationMinutes.
-    final lastPingDateTime = sessionFile.lastModifiedSync();
-    if (now.difference(lastPingDateTime).inMinutes > kSessionDurationMinutes) {
-      // Update the session file with the latest session id
-      _sessionId = now.millisecondsSinceEpoch;
-      writeSessionContents(sessionFile: sessionFile);
-    } else {
-      // Update the last modified timestamp with the current timestamp so that
-      // we can use it for the next _lastPing calculation
-      sessionFile.setLastModifiedSync(now);
-    }
-
-    return _sessionId;
-  }
-
-  /// Preps the [Session] class with the data found in the session file.
-  ///
-  /// We must check if telemetry is enabled to refresh the session data
-  /// because the refresh method will write to the session file and for
-  /// users that have opted out, we have to leave the session file empty
-  /// per the privacy document
-  void initialize(bool telemetryEnabled) {
-    if (telemetryEnabled) _refreshSessionData();
-  }
-
-  /// This will go to the session file within the dart-tool
-  /// directory and fetch the latest data from the session file to update
-  /// the class's variables. If the session file is malformed, a new
-  /// session file will be recreated.
-  ///
-  /// This allows the session data in this class to always be up
-  /// to date incase another tool is also calling this package and
-  /// making updates to the session file.
-  void _refreshSessionData() {
-    /// Using a nested function here to reduce verbosity
-    void parseContents() {
-      final sessionFileContents = sessionFile.readAsStringSync();
-      final sessionObj =
-          jsonDecode(sessionFileContents) as Map<String, Object?>;
-      _sessionId = sessionObj['session_id'] as int;
-    }
-
-    try {
-      // Failing to parse the contents will result in the current timestamp
-      // being used as the session id and will get used to recreate the file
-      parseContents();
-    } on FormatException catch (err) {
-      final now = clock.now();
-      Initializer.createSessionFile(
-        sessionFile: sessionFile,
-        sessionIdOverride: now,
-      );
-
-      _errorHandler.log(Event.analyticsException(
-        workflow: 'Session._refreshSessionData',
-        error: err.runtimeType.toString(),
-        description: 'message: ${err.message}\nsource: ${err.source}',
-      ));
-
-      // Fallback to setting the session id as the current time
-      _sessionId = now.millisecondsSinceEpoch;
-    } on FileSystemException catch (err) {
-      final now = clock.now();
-      Initializer.createSessionFile(
-        sessionFile: sessionFile,
-        sessionIdOverride: now,
-      );
-
-      _errorHandler.log(Event.analyticsException(
-        workflow: 'Session._refreshSessionData',
-        error: err.runtimeType.toString(),
-        description: err.osError?.toString(),
-      ));
-
-      // Fallback to setting the session id as the current time
-      _sessionId = now.millisecondsSinceEpoch;
-    }
-  }
-}
diff --git a/pkgs/unified_analytics/lib/src/survey_handler.dart b/pkgs/unified_analytics/lib/src/survey_handler.dart
index 4925601127..cc533475e2 100644
--- a/pkgs/unified_analytics/lib/src/survey_handler.dart
+++ b/pkgs/unified_analytics/lib/src/survey_handler.dart
@@ -7,7 +7,6 @@ import 'dart:convert';
 import 'package:clock/clock.dart';
 import 'package:file/file.dart';
 import 'package:http/http.dart' as http;
-import 'package:path/path.dart' as p;
 
 import 'constants.dart';
 import 'enums.dart';
@@ -190,16 +189,9 @@ class SurveyButton {
 }
 
 class SurveyHandler {
-  final File _dismissedSurveyFile;
+  final File dismissedSurveyFile;
 
-  SurveyHandler({
-    required Directory homeDirectory,
-    required FileSystem fs,
-  }) : _dismissedSurveyFile = fs.file(p.join(
-          homeDirectory.path,
-          kDartToolDirectoryName,
-          kDismissedSurveyFileName,
-        ));
+  SurveyHandler({required this.dismissedSurveyFile});
 
   /// Invoking this method will persist the survey's id in
   /// the local file with either a snooze or permanently dismissed
@@ -227,7 +219,7 @@ class SurveyHandler {
       'timestamp': clock.now().millisecondsSinceEpoch,
     };
 
-    _dismissedSurveyFile.writeAsStringSync(jsonEncode(contents));
+    dismissedSurveyFile.writeAsStringSync(jsonEncode(contents));
   }
 
   /// Retrieve a list of strings for each [Survey] persisted on disk.
@@ -284,15 +276,13 @@ class SurveyHandler {
   Map<String, dynamic> _parseJsonFile() {
     Map<String, dynamic> contents;
     try {
-      contents = jsonDecode(_dismissedSurveyFile.readAsStringSync())
+      contents = jsonDecode(dismissedSurveyFile.readAsStringSync())
           as Map<String, dynamic>;
     } on FormatException {
-      Initializer.createDismissedSurveyFile(
-          dismissedSurveyFile: _dismissedSurveyFile);
+      createDismissedSurveyFile(dismissedSurveyFile: dismissedSurveyFile);
       contents = {};
     } on FileSystemException {
-      Initializer.createDismissedSurveyFile(
-          dismissedSurveyFile: _dismissedSurveyFile);
+      createDismissedSurveyFile(dismissedSurveyFile: dismissedSurveyFile);
       contents = {};
     }
 
@@ -342,8 +332,7 @@ class FakeSurveyHandler extends SurveyHandler {
   /// will have their dates checked to ensure they are valid; it is
   /// recommended to use `package:clock` to set a fixed time for testing.
   FakeSurveyHandler.fromList({
-    required super.homeDirectory,
-    required super.fs,
+    required super.dismissedSurveyFile,
     required List<Survey> initializedSurveys,
   }) {
     // We must pass the surveys from the list to the
@@ -360,8 +349,7 @@ class FakeSurveyHandler extends SurveyHandler {
   /// Use this class in tests if you can provide raw
   /// json strings to simulate a response from a remote server.
   FakeSurveyHandler.fromString({
-    required super.homeDirectory,
-    required super.fs,
+    required super.dismissedSurveyFile,
     required String content,
   }) {
     final body = jsonDecode(content) as List<dynamic>;
diff --git a/pkgs/unified_analytics/lib/src/user_property.dart b/pkgs/unified_analytics/lib/src/user_property.dart
index 33d0e475f4..d1a8bc0717 100644
--- a/pkgs/unified_analytics/lib/src/user_property.dart
+++ b/pkgs/unified_analytics/lib/src/user_property.dart
@@ -5,13 +5,14 @@
 import 'dart:convert';
 
 import 'package:clock/clock.dart';
+import 'package:file/file.dart';
 
 import 'constants.dart';
-import 'session.dart';
+import 'event.dart';
+import 'initializer.dart';
 import 'utils.dart';
 
 class UserProperty {
-  final Session session;
   final String? flutterChannel;
   final String host;
   final String? flutterVersion;
@@ -22,11 +23,18 @@ class UserProperty {
   final String? clientIde;
   final String? enabledFeatures;
 
+  final File sessionFile;
+
+  /// Contains instances of [Event.analyticsException] that were encountered
+  /// during a workflow and will be sent to GA4 for collection.
+  final Set<Event> errorSet = {};
+
+  int? _sessionId;
+
   /// This class is intended to capture all of the user's
   /// metadata when the class gets initialized as well as collecting
   /// session data to send in the json payload to Google Analytics.
   UserProperty({
-    required this.session,
     required this.flutterChannel,
     required this.host,
     required this.flutterVersion,
@@ -36,13 +44,45 @@ class UserProperty {
     required this.locale,
     required this.clientIde,
     required this.enabledFeatures,
+    required this.sessionFile,
   });
 
+  /// This will use the data parsed from the
+  /// session file in the dart-tool directory
+  /// to get the session id if the last ping was within
+  /// [kSessionDurationMinutes].
+  ///
+  /// If time since last ping exceeds the duration, then the file
+  /// will be updated with a new session id and that will be returned.
+  ///
+  /// Note, the file will always be updated when calling this method
+  /// because the last ping variable will always need to be persisted.
+  int? getSessionId() {
+    _refreshSessionData();
+    final now = clock.now();
+
+    // Convert the epoch time from the last ping into datetime and check if we
+    // are within the kSessionDurationMinutes.
+    final lastPingDateTime = sessionFile.lastModifiedSync();
+    if (now.difference(lastPingDateTime).inMinutes > kSessionDurationMinutes) {
+      // Update the session file with the latest session id
+      _sessionId = now.millisecondsSinceEpoch;
+      writeSessionContents(sessionFile: sessionFile);
+    } else {
+      // Update the last modified timestamp with the current timestamp so that
+      // we can use it for the next _lastPing calculation
+      sessionFile.setLastModifiedSync(now);
+    }
+
+    return _sessionId;
+  }
+
   /// This method will take the data in this class and convert it into
   /// a Map that is suitable for the POST request schema.
   ///
-  /// This will call the [Session] object's [Session.getSessionId] method which
-  /// will update the session file and get a new session id if necessary.
+  /// This will call the [UserProperty] object's [UserProperty.getSessionId]
+  /// method which will update the session file and get a new session id
+  /// if necessary.
   ///
   /// https://developers.google.com/analytics/devguides/collection/protocol/ga4/user-properties?client_type=gtag
   Map<String, Map<String, Object?>> preparePayload() {
@@ -57,10 +97,56 @@ class UserProperty {
     return jsonEncode(_toMap());
   }
 
+  /// This will go to the session file within the dart-tool
+  /// directory and fetch the latest data from the session file to update
+  /// the class's variables. If the session file is malformed, a new
+  /// session file will be recreated.
+  ///
+  /// This allows the session data in this class to always be up
+  /// to date incase another tool is also calling this package and
+  /// making updates to the session file.
+  void _refreshSessionData() {
+    /// Using a nested function here to reduce verbosity
+    void parseContents() {
+      final sessionFileContents = sessionFile.readAsStringSync();
+      final sessionObj =
+          jsonDecode(sessionFileContents) as Map<String, Object?>;
+      _sessionId = sessionObj['session_id'] as int;
+    }
+
+    try {
+      // Failing to parse the contents will result in the current timestamp
+      // being used as the session id and will get used to recreate the file
+      parseContents();
+    } on FormatException catch (err) {
+      final now = createSessionFile(sessionFile: sessionFile);
+
+      errorSet.add(Event.analyticsException(
+        workflow: 'UserProperty._refreshSessionData',
+        error: err.runtimeType.toString(),
+        description: 'message: ${err.message}\nsource: ${err.source}',
+      ));
+
+      // Fallback to setting the session id as the current time
+      _sessionId = now.millisecondsSinceEpoch;
+    } on FileSystemException catch (err) {
+      final now = createSessionFile(sessionFile: sessionFile);
+
+      errorSet.add(Event.analyticsException(
+        workflow: 'UserProperty._refreshSessionData',
+        error: err.runtimeType.toString(),
+        description: err.osError?.toString(),
+      ));
+
+      // Fallback to setting the session id as the current time
+      _sessionId = now.millisecondsSinceEpoch;
+    }
+  }
+
   /// Convert the data stored in this class into a map while also
-  /// getting the latest session id using the [Session] class.
+  /// getting the latest session id using the [UserProperty] class.
   Map<String, Object?> _toMap() => <String, Object?>{
-        'session_id': session.getSessionId(),
+        'session_id': getSessionId(),
         'flutter_channel': flutterChannel,
         'host': host,
         'flutter_version': flutterVersion,
diff --git a/pkgs/unified_analytics/pubspec.yaml b/pkgs/unified_analytics/pubspec.yaml
index 9788d8f13a..02ac8d2edf 100644
--- a/pkgs/unified_analytics/pubspec.yaml
+++ b/pkgs/unified_analytics/pubspec.yaml
@@ -4,7 +4,7 @@ description: >-
   to Google Analytics.
 # When updating this, keep the version consistent with the changelog and the
 # value in lib/src/constants.dart.
-version: 5.8.8
+version: 6.0.0-wip
 repository: https://github.com/dart-lang/tools/tree/main/pkgs/unified_analytics
 
 environment:
diff --git a/pkgs/unified_analytics/test/error_handler_test.dart b/pkgs/unified_analytics/test/error_handler_test.dart
index c7156e2aaf..22decf72d7 100644
--- a/pkgs/unified_analytics/test/error_handler_test.dart
+++ b/pkgs/unified_analytics/test/error_handler_test.dart
@@ -139,6 +139,7 @@ void main() {
       analytics.send(testEvent);
       expect(sessionFile.readAsStringSync(), isNotEmpty);
 
+      analytics.sendPendingErrorEvents();
       expect(
           analytics.sentEvents.where(
               (element) => element.eventName == DashEvent.analyticsException),
@@ -167,6 +168,7 @@ void main() {
       expect(sessionFile.existsSync(), isFalse);
       analytics.send(testEvent);
 
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -198,6 +200,7 @@ void main() {
       analytics.send(testEvent);
       expect(sessionFile.readAsStringSync(), isNotEmpty);
 
+      analytics.sendPendingErrorEvents();
       expect(
           analytics.sentEvents.where(
               (element) => element.eventName == DashEvent.analyticsException),
@@ -210,6 +213,7 @@ void main() {
 
       analytics.send(testEvent);
       expect(sessionFile.readAsStringSync(), isNotEmpty);
+      analytics.sendPendingErrorEvents();
       expect(
           analytics.sentEvents.where(
               (element) => element.eventName == DashEvent.analyticsException),
@@ -243,6 +247,7 @@ void main() {
       analytics.send(testEvent);
       expect(analytics.sentEvents, hasLength(1));
       expect(logFile.readAsLinesSync(), hasLength(3));
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -254,6 +259,7 @@ void main() {
       expect(logFileStats, isNotNull);
       expect(logFileStats!.recordCount, 1,
           reason: 'The error event is not counted');
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -278,6 +284,7 @@ void main() {
       analytics.send(testEvent);
 
       final logFileStats = analytics.logFileStats();
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -301,6 +308,7 @@ void main() {
       analytics.send(testEvent);
       expect(analytics.sentEvents, hasLength(1));
       expect(logFile.readAsLinesSync(), hasLength(3));
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -309,6 +317,7 @@ void main() {
 
       // This will cause the first error
       analytics.logFileStats();
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -325,6 +334,7 @@ void main() {
 
       // This will cause the second error
       analytics.logFileStats();
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
@@ -333,6 +343,7 @@ void main() {
 
       // Attempting to cause the same error won't send another error event
       analytics.logFileStats();
+      analytics.sendPendingErrorEvents();
       expect(
         analytics.sentEvents.where(
             (element) => element.eventName == DashEvent.analyticsException),
diff --git a/pkgs/unified_analytics/test/events_with_fake_test.dart b/pkgs/unified_analytics/test/events_with_fake_test.dart
index 2a07c1656c..890d701ef6 100644
--- a/pkgs/unified_analytics/test/events_with_fake_test.dart
+++ b/pkgs/unified_analytics/test/events_with_fake_test.dart
@@ -5,8 +5,10 @@
 import 'package:clock/clock.dart';
 import 'package:file/file.dart';
 import 'package:file/memory.dart';
+import 'package:path/path.dart' as p;
 import 'package:test/test.dart';
 
+import 'package:unified_analytics/src/constants.dart';
 import 'package:unified_analytics/src/enums.dart';
 import 'package:unified_analytics/src/survey_handler.dart';
 import 'package:unified_analytics/unified_analytics.dart';
@@ -18,6 +20,7 @@ void main() {
   late FakeAnalytics fakeAnalytics;
   late FileSystem fs;
   late Directory homeDirectory;
+  late File dismissedSurveyFile;
 
   /// Survey to load into the fake instance to fetch
   ///
@@ -49,6 +52,11 @@ void main() {
   setUp(() async {
     fs = MemoryFileSystem.test(style: FileSystemStyle.posix);
     homeDirectory = fs.directory('home');
+    dismissedSurveyFile = fs.file(p.join(
+      homeDirectory.path,
+      kDartToolDirectoryName,
+      kDismissedSurveyFileName,
+    ));
 
     final initialAnalytics = Analytics.test(
       tool: DashTool.flutterTool,
@@ -65,17 +73,19 @@ void main() {
     // Recreate a second instance since events cannot be sent on
     // the first run
     withClock(Clock.fixed(DateTime(2022, 3, 3)), () {
+      final toolsMessageVersion = kToolsMessageVersion;
       fakeAnalytics = FakeAnalytics(
         tool: DashTool.flutterTool,
         homeDirectory: homeDirectory,
         dartVersion: 'dartVersion',
         platform: DevicePlatform.macos,
         fs: fs,
+        toolsMessageVersion: toolsMessageVersion,
         surveyHandler: FakeSurveyHandler.fromList(
-          homeDirectory: homeDirectory,
-          fs: fs,
+          dismissedSurveyFile: dismissedSurveyFile,
           initializedSurveys: [testSurvey],
         ),
+        firstRun: false,
       );
     });
   });
diff --git a/pkgs/unified_analytics/test/log_handler_test.dart b/pkgs/unified_analytics/test/log_handler_test.dart
index a1f494a6ee..fa5e15ff6e 100644
--- a/pkgs/unified_analytics/test/log_handler_test.dart
+++ b/pkgs/unified_analytics/test/log_handler_test.dart
@@ -74,7 +74,7 @@ void main() {
     expect(analytics.logFileStats()!.recordCount, countOfEventsToSend);
   });
 
-  test('The only record in the log file is malformed', () {
+  test('The only record in the log file is malformed', () async {
     // Write invalid json for the only log record
     logFile.writeAsStringSync('{{\n');
 
@@ -83,6 +83,8 @@ void main() {
     expect(logFileStats, isNull,
         reason: 'Null should be returned since only '
             'one record is in there and it is malformed');
+
+    analytics.sendPendingErrorEvents();
     expect(
         analytics.sentEvents,
         contains(
@@ -126,6 +128,8 @@ void main() {
     expect(logFile.readAsLinesSync().length,
         countOfEventsToSend + countOfMalformedRecords);
     final logFileStats = analytics.logFileStats();
+
+    analytics.sendPendingErrorEvents();
     expect(logFile.readAsLinesSync().length,
         countOfEventsToSend + countOfMalformedRecords + 1,
         reason:
@@ -172,6 +176,7 @@ void main() {
       analytics.send(testEvent);
     }
     final logFileStats = analytics.logFileStats();
+    analytics.sendPendingErrorEvents();
     expect(analytics.sentEvents.last.eventName, DashEvent.analyticsException,
         reason: 'Calling for the stats should have caused an error');
     expect(logFile.readAsLinesSync().length, kLogFileLength);
@@ -203,6 +208,7 @@ void main() {
     for (var i = 0; i < countOfEventsToSend; i++) {
       analytics.send(testEvent);
     }
+    analytics.sendPendingErrorEvents();
     final secondLogFileStats = analytics.logFileStats();
 
     expect(secondLogFileStats, isNotNull);
diff --git a/pkgs/unified_analytics/test/survey_handler_test.dart b/pkgs/unified_analytics/test/survey_handler_test.dart
index 908a654c55..d55ab02471 100644
--- a/pkgs/unified_analytics/test/survey_handler_test.dart
+++ b/pkgs/unified_analytics/test/survey_handler_test.dart
@@ -328,8 +328,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[
               Survey(
                 uniqueId: 'uniqueId',
@@ -382,8 +381,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[
               Survey(
                 uniqueId: 'uniqueId',
@@ -425,8 +423,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[
               Survey(
                 uniqueId: 'uniqueId',
@@ -471,7 +468,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromString(
-              homeDirectory: homeDirectory, fs: fs, content: '''
+              dismissedSurveyFile: dismissedSurveyFile, content: '''
 [
     {
         "uniqueId": "uniqueId123",
@@ -573,7 +570,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromString(
-              homeDirectory: homeDirectory, fs: fs, content: '''
+              dismissedSurveyFile: dismissedSurveyFile, content: '''
 [
     {
         "uniqueId": "uniqueId123",
@@ -637,7 +634,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromString(
-              homeDirectory: homeDirectory, fs: fs, content: '''
+              dismissedSurveyFile: dismissedSurveyFile, content: '''
 [
     {
         "uniqueId": "12345",
@@ -720,8 +717,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[
               Survey(
                 uniqueId: 'uniqueId',
@@ -797,8 +793,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[survey],
           ),
         );
@@ -843,8 +838,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[survey],
           ),
         );
@@ -891,8 +885,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -921,8 +914,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -943,8 +935,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -990,8 +981,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -1019,8 +1009,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -1068,8 +1057,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -1101,8 +1089,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -1150,8 +1137,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -1180,8 +1166,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[surveyToLoad],
           ),
         );
@@ -1205,8 +1190,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[
               Survey(
                 uniqueId: 'uniqueId',
@@ -1253,8 +1237,7 @@ void main() {
           fs: fs,
           platform: DevicePlatform.macos,
           surveyHandler: FakeSurveyHandler.fromList(
-            homeDirectory: homeDirectory,
-            fs: fs,
+            dismissedSurveyFile: dismissedSurveyFile,
             initializedSurveys: <Survey>[
               Survey(
                 uniqueId: 'uniqueId',
diff --git a/pkgs/unified_analytics/test/unified_analytics_test.dart b/pkgs/unified_analytics/test/unified_analytics_test.dart
index 55d20010c6..e466c80fa7 100644
--- a/pkgs/unified_analytics/test/unified_analytics_test.dart
+++ b/pkgs/unified_analytics/test/unified_analytics_test.dart
@@ -146,12 +146,15 @@ void main() {
       expect(sessionFile.readAsStringSync(),
           '{"session_id": $timestamp, "last_ping": $timestamp}');
 
+      analytics.sendPendingErrorEvents();
+
       // Attempting to fetch the session id when malformed should also
       // send an error event while parsing
       final lastEvent = analytics.sentEvents.last;
       expect(lastEvent, isNotNull);
       expect(lastEvent.eventName, DashEvent.analyticsException);
-      expect(lastEvent.eventData['workflow']!, 'Session._refreshSessionData');
+      expect(
+          lastEvent.eventData['workflow']!, 'UserProperty._refreshSessionData');
       expect(lastEvent.eventData['error']!, 'FormatException');
     });
   });
@@ -178,11 +181,19 @@ void main() {
     ) as FakeAnalytics;
     analytics.clientShowedMessage();
 
+    // Invoking a send command should reset the session file to a good state
+    //
+    // Having it reformat the session file before any send event happens will just
+    // add additional work on startup
+    analytics.send(testEvent);
+
+    analytics.sendPendingErrorEvents();
     final errorEvent = analytics.sentEvents
         .where((element) => element.eventName == DashEvent.analyticsException)
         .firstOrNull;
     expect(errorEvent, isNotNull);
-    expect(errorEvent!.eventData['workflow'], 'Session._refreshSessionData');
+    expect(
+        errorEvent!.eventData['workflow'], 'UserProperty._refreshSessionData');
     expect(errorEvent.eventData['error'], 'FormatException');
     expect(errorEvent.eventData['description'],
         'message: Unexpected character\nsource: not a valid session id');
@@ -203,12 +214,15 @@ void main() {
       expect(sessionFile.readAsStringSync(),
           '{"session_id": $timestamp, "last_ping": $timestamp}');
 
+      analytics.sendPendingErrorEvents();
+
       // Attempting to fetch the session id when malformed should also
       // send an error event while parsing
       final lastEvent = analytics.sentEvents.last;
       expect(lastEvent, isNotNull);
       expect(lastEvent.eventName, DashEvent.analyticsException);
-      expect(lastEvent.eventData['workflow']!, 'Session._refreshSessionData');
+      expect(
+          lastEvent.eventData['workflow']!, 'UserProperty._refreshSessionData');
       expect(lastEvent.eventData['error']!, 'FileSystemException');
     });
   });