diff --git a/airbyte-webapp/src/App.tsx b/airbyte-webapp/src/App.tsx
index 4a18cf5bbaa8..7843bb1d6c20 100644
--- a/airbyte-webapp/src/App.tsx
+++ b/airbyte-webapp/src/App.tsx
@@ -8,6 +8,7 @@ import { ApiErrorBoundary } from "components/common/ApiErrorBoundary";
 import { ApiServices } from "core/ApiServices";
 import { I18nProvider } from "core/i18n";
 import { ServicesProvider } from "core/servicesProvider";
+import { AppMonitoringServiceProvider } from "hooks/services/AppMonitoringService";
 import { ConfirmationModalService } from "hooks/services/ConfirmationModal";
 import { defaultFeatures, FeatureService } from "hooks/services/Feature";
 import { FormChangeTrackerService } from "hooks/services/FormChangeTracker";
@@ -38,23 +39,25 @@ const configProviders: ValueProvider<Config> = [envConfigProvider, windowConfigP
 
 const Services: React.FC<React.PropsWithChildren<unknown>> = ({ children }) => (
   <AnalyticsProvider>
-    <ApiErrorBoundary>
-      <WorkspaceServiceProvider>
-        <FeatureService features={defaultFeatures}>
-          <NotificationService>
-            <ConfirmationModalService>
-              <ModalServiceProvider>
-                <FormChangeTrackerService>
-                  <HelmetProvider>
-                    <ApiServices>{children}</ApiServices>
-                  </HelmetProvider>
-                </FormChangeTrackerService>
-              </ModalServiceProvider>
-            </ConfirmationModalService>
-          </NotificationService>
-        </FeatureService>
-      </WorkspaceServiceProvider>
-    </ApiErrorBoundary>
+    <AppMonitoringServiceProvider>
+      <ApiErrorBoundary>
+        <WorkspaceServiceProvider>
+          <FeatureService features={defaultFeatures}>
+            <NotificationService>
+              <ConfirmationModalService>
+                <ModalServiceProvider>
+                  <FormChangeTrackerService>
+                    <HelmetProvider>
+                      <ApiServices>{children}</ApiServices>
+                    </HelmetProvider>
+                  </FormChangeTrackerService>
+                </ModalServiceProvider>
+              </ConfirmationModalService>
+            </NotificationService>
+          </FeatureService>
+        </WorkspaceServiceProvider>
+      </ApiErrorBoundary>
+    </AppMonitoringServiceProvider>
   </AnalyticsProvider>
 );
 
diff --git a/airbyte-webapp/src/hooks/services/AppMonitoringService/AppMonitoringService.tsx b/airbyte-webapp/src/hooks/services/AppMonitoringService/AppMonitoringService.tsx
new file mode 100644
index 000000000000..8f44132b9700
--- /dev/null
+++ b/airbyte-webapp/src/hooks/services/AppMonitoringService/AppMonitoringService.tsx
@@ -0,0 +1,56 @@
+import { datadogRum } from "@datadog/browser-rum";
+import React, { createContext, useContext } from "react";
+
+import { AppActionCodes } from "./actionCodes";
+
+const appMonitoringContext = createContext<AppMonitoringServiceProviderValue | null>(null);
+
+/**
+ * The AppMonitoringService exposes methods for tracking actions and errors from the webapp.
+ * These methods are particularly useful for tracking when unexpected or edge-case conditions
+ * are encountered in production.
+ */
+interface AppMonitoringServiceProviderValue {
+  /**
+   * Log a custom action in datadog. Useful for tracking edge cases or unexpected application states.
+   */
+  trackAction: (actionCode: AppActionCodes, context?: Record<string, unknown>) => void;
+  /**
+   * Log a custom error in datadog. Useful for tracking edge case errors while handling them in the UI.
+   */
+  trackError: (error: Error, context?: Record<string, unknown>) => void;
+}
+
+export const useAppMonitoringService = (): AppMonitoringServiceProviderValue => {
+  const context = useContext(appMonitoringContext);
+  if (context === null) {
+    throw new Error("useAppMonitoringService must be used within a AppMonitoringServiceProvider");
+  }
+
+  return context;
+};
+
+/**
+ * This implementation of the AppMonitoringService uses the datadog SDK to track errors and actions
+ */
+export const AppMonitoringServiceProvider: React.FC<React.PropsWithChildren<unknown>> = ({ children }) => {
+  const trackAction = (action: string, context?: Record<string, unknown>) => {
+    if (!datadogRum.getInternalContext()) {
+      console.debug(`trackAction(${action}) failed because RUM is not initialized.`);
+      return;
+    }
+
+    datadogRum.addAction(action, context);
+  };
+
+  const trackError = (error: Error, context?: Record<string, unknown>) => {
+    if (!datadogRum.getInternalContext()) {
+      console.debug(`trackError() failed because RUM is not initialized. \n`, error);
+      return;
+    }
+
+    datadogRum.addError(error, context);
+  };
+
+  return <appMonitoringContext.Provider value={{ trackAction, trackError }}>{children}</appMonitoringContext.Provider>;
+};
diff --git a/airbyte-webapp/src/hooks/services/AppMonitoringService/actionCodes.ts b/airbyte-webapp/src/hooks/services/AppMonitoringService/actionCodes.ts
new file mode 100644
index 000000000000..ddcbe000a02a
--- /dev/null
+++ b/airbyte-webapp/src/hooks/services/AppMonitoringService/actionCodes.ts
@@ -0,0 +1,11 @@
+/**
+ * Action codes are used to log specific runtime events that we want to analyse in datadog.
+ * This is useful for tracking when and how frequently certain code paths on the frontend are
+ * encountered in production.
+ */
+export enum AppActionCodes {
+  /**
+   * LaunchDarkly did not load in time and was ignored
+   */
+  LD_LOAD_TIMEOUT = "LD_LOAD_TIMEOUT",
+}
diff --git a/airbyte-webapp/src/hooks/services/AppMonitoringService/index.ts b/airbyte-webapp/src/hooks/services/AppMonitoringService/index.ts
new file mode 100644
index 000000000000..ba69c7120194
--- /dev/null
+++ b/airbyte-webapp/src/hooks/services/AppMonitoringService/index.ts
@@ -0,0 +1,2 @@
+export { AppMonitoringServiceProvider, useAppMonitoringService } from "./AppMonitoringService";
+export { AppActionCodes } from "./actionCodes";
diff --git a/airbyte-webapp/src/packages/cloud/App.tsx b/airbyte-webapp/src/packages/cloud/App.tsx
index d149224407e6..18f6d7e5116c 100644
--- a/airbyte-webapp/src/packages/cloud/App.tsx
+++ b/airbyte-webapp/src/packages/cloud/App.tsx
@@ -7,6 +7,7 @@ import { ApiErrorBoundary } from "components/common/ApiErrorBoundary";
 import LoadingPage from "components/LoadingPage";
 
 import { I18nProvider } from "core/i18n";
+import { AppMonitoringServiceProvider } from "hooks/services/AppMonitoringService";
 import { ConfirmationModalService } from "hooks/services/ConfirmationModal";
 import { FeatureItem, FeatureService } from "hooks/services/Feature";
 import { FormChangeTrackerService } from "hooks/services/FormChangeTracker";
@@ -32,31 +33,33 @@ const StyleProvider: React.FC<React.PropsWithChildren<unknown>> = ({ children })
 
 const Services: React.FC<React.PropsWithChildren<unknown>> = ({ children }) => (
   <AnalyticsProvider>
-    <ApiErrorBoundary>
-      <NotificationServiceProvider>
-        <ConfirmationModalService>
-          <ModalServiceProvider>
-            <FormChangeTrackerService>
-              <FeatureService
-                features={[
-                  FeatureItem.AllowOAuthConnector,
-                  FeatureItem.AllowSync,
-                  FeatureItem.AllowChangeDataGeographies,
-                ]}
-              >
-                <AppServicesProvider>
-                  <AuthenticationProvider>
-                    <HelmetProvider>
-                      <IntercomProvider>{children}</IntercomProvider>
-                    </HelmetProvider>
-                  </AuthenticationProvider>
-                </AppServicesProvider>
-              </FeatureService>
-            </FormChangeTrackerService>
-          </ModalServiceProvider>
-        </ConfirmationModalService>
-      </NotificationServiceProvider>
-    </ApiErrorBoundary>
+    <AppMonitoringServiceProvider>
+      <ApiErrorBoundary>
+        <NotificationServiceProvider>
+          <ConfirmationModalService>
+            <ModalServiceProvider>
+              <FormChangeTrackerService>
+                <FeatureService
+                  features={[
+                    FeatureItem.AllowOAuthConnector,
+                    FeatureItem.AllowSync,
+                    FeatureItem.AllowChangeDataGeographies,
+                  ]}
+                >
+                  <AppServicesProvider>
+                    <AuthenticationProvider>
+                      <HelmetProvider>
+                        <IntercomProvider>{children}</IntercomProvider>
+                      </HelmetProvider>
+                    </AuthenticationProvider>
+                  </AppServicesProvider>
+                </FeatureService>
+              </FormChangeTrackerService>
+            </ModalServiceProvider>
+          </ConfirmationModalService>
+        </NotificationServiceProvider>
+      </ApiErrorBoundary>
+    </AppMonitoringServiceProvider>
   </AnalyticsProvider>
 );
 
diff --git a/airbyte-webapp/src/packages/cloud/services/thirdParty/launchdarkly/LDExperimentService.tsx b/airbyte-webapp/src/packages/cloud/services/thirdParty/launchdarkly/LDExperimentService.tsx
index 9729ecd8dc4f..0c8881f9e3cc 100644
--- a/airbyte-webapp/src/packages/cloud/services/thirdParty/launchdarkly/LDExperimentService.tsx
+++ b/airbyte-webapp/src/packages/cloud/services/thirdParty/launchdarkly/LDExperimentService.tsx
@@ -9,6 +9,7 @@ import { LoadingPage } from "components";
 import { useConfig } from "config";
 import { useI18nContext } from "core/i18n";
 import { useAnalyticsService } from "hooks/services/Analytics";
+import { useAppMonitoringService, AppActionCodes } from "hooks/services/AppMonitoringService";
 import { ExperimentProvider, ExperimentService } from "hooks/services/Experiment";
 import type { Experiments } from "hooks/services/Experiment/experiments";
 import { FeatureSet, useFeatureService } from "hooks/services/Feature";
@@ -49,6 +50,7 @@ const LDInitializationWrapper: React.FC<React.PropsWithChildren<{ apiKey: string
   const analyticsService = useAnalyticsService();
   const { locale } = useIntl();
   const { setMessageOverwrite } = useI18nContext();
+  const { trackAction } = useAppMonitoringService();
 
   /**
    * This function checks for all experiments to find the ones beginning with "i18n_{locale}_"
@@ -87,7 +89,7 @@ const LDInitializationWrapper: React.FC<React.PropsWithChildren<{ apiKey: string
     // Wait for either LaunchDarkly to initialize or a specific timeout to pass first
     Promise.race([
       ldClient.current.waitForInitialization(),
-      rejectAfter(INITIALIZATION_TIMEOUT, "Timed out waiting for LaunchDarkly to initialize"),
+      rejectAfter(INITIALIZATION_TIMEOUT, AppActionCodes.LD_LOAD_TIMEOUT),
     ])
       .then(() => {
         // The LaunchDarkly promise resolved before the timeout, so we're good to use LD.
@@ -103,6 +105,9 @@ const LDInitializationWrapper: React.FC<React.PropsWithChildren<{ apiKey: string
         // our timeout promise resolves first, we're going to show an error and assume the service
         // failed to initialize, i.e. we'll run without it.
         console.warn(`Failed to initialize LaunchDarkly service with reason: ${String(reason)}`);
+        if (reason === AppActionCodes.LD_LOAD_TIMEOUT) {
+          trackAction(AppActionCodes.LD_LOAD_TIMEOUT);
+        }
         setState("failed");
       });
   }