diff --git a/Core/PixelEvent.swift b/Core/PixelEvent.swift
index 60da1bb74a..d8a87f3132 100644
--- a/Core/PixelEvent.swift
+++ b/Core/PixelEvent.swift
@@ -416,6 +416,9 @@ extension Pixel {
         case networkProtectionDNSUpdateCustom
         case networkProtectionDNSUpdateDefault
 
+        case networkProtectionVPNConfigurationRemoved
+        case networkProtectionVPNConfigurationRemovalFailed
+
         // MARK: remote messaging pixels
         
         case remoteMessageShown
@@ -1102,6 +1105,9 @@ extension Pixel.Event {
         case .networkProtectionDNSUpdateCustom: return "m_netp_ev_update_dns_custom"
         case .networkProtectionDNSUpdateDefault: return "m_netp_ev_update_dns_default"
 
+        case .networkProtectionVPNConfigurationRemoved: return "m_netp_vpn_configuration_removed"
+        case .networkProtectionVPNConfigurationRemovalFailed: return "m_netp_vpn_configuration_removal_failed"
+
             // MARK: remote messaging pixels
             
         case .remoteMessageShown: return "m_remote_message_shown"
diff --git a/DuckDuckGo/AppDelegate.swift b/DuckDuckGo/AppDelegate.swift
index d33015d5df..ef4149ff99 100644
--- a/DuckDuckGo/AppDelegate.swift
+++ b/DuckDuckGo/AppDelegate.swift
@@ -512,8 +512,6 @@ import WebKit
 #if NETWORK_PROTECTION
         widgetRefreshModel.refreshVPNWidget()
 
-        stopTunnelAndShowThankYouMessagingIfNeeded()
-
         if tunnelDefaults.showEntitlementAlert {
             presentExpiredEntitlementAlert()
         }
@@ -521,6 +519,7 @@ import WebKit
         presentExpiredEntitlementNotificationIfNeeded()
 
         Task {
+            await stopAndRemoveVPNIfNotAuthenticated()
             await refreshShortcuts()
             await vpnWorkaround.installRedditSessionWorkaround()
         }
@@ -536,25 +535,14 @@ import WebKit
         importPasswordsStatusHandler.checkSyncSuccessStatus()
     }
 
-    private func stopTunnelAndShowThankYouMessagingIfNeeded() {
-        if accountManager.isUserAuthenticated {
-            return
-        }
-
-        if AppDependencyProvider.shared.vpnFeatureVisibility.isPrivacyProLaunched() && !accountManager.isUserAuthenticated {
-            Task {
-                await self.stopAndRemoveVPN(with: "subscription-check")
-            }
-        }
-    }
-
-    private func stopAndRemoveVPN(with reason: String) async {
-        guard await AppDependencyProvider.shared.networkProtectionTunnelController.isInstalled else {
+    private func stopAndRemoveVPNIfNotAuthenticated() async {
+        // Only remove the VPN if the user is not authenticated, and it's installed:
+        guard !accountManager.isUserAuthenticated, await AppDependencyProvider.shared.networkProtectionTunnelController.isInstalled else {
             return
         }
 
         await AppDependencyProvider.shared.networkProtectionTunnelController.stop()
-        await AppDependencyProvider.shared.networkProtectionTunnelController.removeVPN()
+        await AppDependencyProvider.shared.networkProtectionTunnelController.removeVPN(reason: .didBecomeActiveCheck)
     }
 
     func applicationWillResignActive(_ application: UIApplication) {
diff --git a/DuckDuckGo/MainViewController.swift b/DuckDuckGo/MainViewController.swift
index 9b68900b42..5b2a294cdc 100644
--- a/DuckDuckGo/MainViewController.swift
+++ b/DuckDuckGo/MainViewController.swift
@@ -1503,7 +1503,7 @@ class MainViewController: UIViewController {
             }
 
             await networkProtectionTunnelController.stop()
-            await networkProtectionTunnelController.removeVPN()
+            await networkProtectionTunnelController.removeVPN(reason: .entitlementCheck)
         }
     }
 
@@ -1511,7 +1511,7 @@ class MainViewController: UIViewController {
     private func onNetworkProtectionAccountSignOut(_ notification: Notification) {
         Task {
             await networkProtectionTunnelController.stop()
-            await networkProtectionTunnelController.removeVPN()
+            await networkProtectionTunnelController.removeVPN(reason: .signedOut)
         }
     }
 #endif
diff --git a/DuckDuckGo/NetworkProtectionDebugViewController.swift b/DuckDuckGo/NetworkProtectionDebugViewController.swift
index 472402a443..c37fa4c53a 100644
--- a/DuckDuckGo/NetworkProtectionDebugViewController.swift
+++ b/DuckDuckGo/NetworkProtectionDebugViewController.swift
@@ -700,7 +700,7 @@ shouldShowVPNShortcut: \(vpnVisibility.shouldShowVPNShortcut() ? "YES" : "NO")
     private func deleteVPNConfiguration() {
         Task {
             await AppDependencyProvider.shared.networkProtectionTunnelController.stop()
-            await AppDependencyProvider.shared.networkProtectionTunnelController.removeVPN()
+            await AppDependencyProvider.shared.networkProtectionTunnelController.removeVPN(reason: .debugMenu)
         }
     }
 }
diff --git a/DuckDuckGo/NetworkProtectionTunnelController.swift b/DuckDuckGo/NetworkProtectionTunnelController.swift
index 80ee7defa2..02f5953de7 100644
--- a/DuckDuckGo/NetworkProtectionTunnelController.swift
+++ b/DuckDuckGo/NetworkProtectionTunnelController.swift
@@ -26,6 +26,13 @@ import NetworkExtension
 import NetworkProtection
 import Subscription
 
+enum VPNConfigurationRemovalReason: String {
+    case didBecomeActiveCheck
+    case entitlementCheck
+    case signedOut
+    case debugMenu
+}
+
 final class NetworkProtectionTunnelController: TunnelController {
     static var shouldSimulateFailure: Bool = false
 
@@ -114,8 +121,18 @@ final class NetworkProtectionTunnelController: TunnelController {
         tunnelManager.connection.stopVPNTunnel()
     }
 
-    func removeVPN() async {
-        try? await tunnelManager?.removeFromPreferences()
+    func removeVPN(reason: VPNConfigurationRemovalReason) async {
+        do {
+            try await tunnelManager?.removeFromPreferences()
+
+            DailyPixel.fireDailyAndCount(pixel: .networkProtectionVPNConfigurationRemoved, withAdditionalParameters: [
+                PixelParameters.reason: reason.rawValue
+            ])
+        } catch {
+            DailyPixel.fireDailyAndCount(pixel: .networkProtectionVPNConfigurationRemovalFailed, error: error, withAdditionalParameters: [
+                PixelParameters.reason: reason.rawValue
+            ])
+        }
     }
 
     // MARK: - Connection Status Querying