diff --git a/Sources/NetworkProtection/PacketTunnelProvider.swift b/Sources/NetworkProtection/PacketTunnelProvider.swift
index d40b104c2..2e980e1f9 100644
--- a/Sources/NetworkProtection/PacketTunnelProvider.swift
+++ b/Sources/NetworkProtection/PacketTunnelProvider.swift
@@ -830,7 +830,8 @@ open class PacketTunnelProvider: NEPacketTunnelProvider {
                 .setNotifyStatusChanges,
                 .setRegistrationKeyValidity,
                 .setSelectedEnvironment,
-                .setShowInMenuBar:
+                .setShowInMenuBar,
+                .setVPNFirstEnabled:
             // Intentional no-op, as some setting changes don't require any further operation
             break
         }
diff --git a/Sources/NetworkProtection/Settings/Extensions/UserDefaults+vpnFirstEnabled.swift b/Sources/NetworkProtection/Settings/Extensions/UserDefaults+vpnFirstEnabled.swift
new file mode 100644
index 000000000..dbf9b1f30
--- /dev/null
+++ b/Sources/NetworkProtection/Settings/Extensions/UserDefaults+vpnFirstEnabled.swift
@@ -0,0 +1,41 @@
+//
+//  UserDefaults+showInMenuBar.swift
+//
+//  Copyright © 2023 DuckDuckGo. All rights reserved.
+//
+//  Licensed under the Apache License, Version 2.0 (the "License");
+//  you may not use this file except in compliance with the License.
+//  You may obtain a copy of the License at
+//
+//  http://www.apache.org/licenses/LICENSE-2.0
+//
+//  Unless required by applicable law or agreed to in writing, software
+//  distributed under the License is distributed on an "AS IS" BASIS,
+//  WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+//  See the License for the specific language governing permissions and
+//  limitations under the License.
+//
+
+import Combine
+import Foundation
+
+extension UserDefaults {
+    private var vpnFirstEnabledKey: String {
+        "vpnFirstEnabled"
+    }
+
+    @objc
+    dynamic var vpnFirstEnabled: Date? {
+        get {
+            value(forKey: vpnFirstEnabledKey) as? Date
+        }
+
+        set {
+            set(newValue, forKey: vpnFirstEnabledKey)
+        }
+    }
+
+    var vpnFirstEnabledPublisher: AnyPublisher<Date?, Never> {
+        publisher(for: \.vpnFirstEnabled).eraseToAnyPublisher()
+    }
+}
diff --git a/Sources/NetworkProtection/Settings/VPNSettings.swift b/Sources/NetworkProtection/Settings/VPNSettings.swift
index 8eeed00b4..a8b21ea94 100644
--- a/Sources/NetworkProtection/Settings/VPNSettings.swift
+++ b/Sources/NetworkProtection/Settings/VPNSettings.swift
@@ -19,7 +19,7 @@
 import Combine
 import Foundation
 
-// swiftlint:disable type_body_length
+// swiftlint:disable type_body_length file_length
 
 /// Persists and publishes changes to tunnel settings.
 ///
@@ -40,6 +40,7 @@ public final class VPNSettings {
         case setSelectedLocation(_ selectedLocation: SelectedLocation)
         case setSelectedEnvironment(_ selectedEnvironment: SelectedEnvironment)
         case setShowInMenuBar(_ showInMenuBar: Bool)
+        case setVPNFirstEnabled(_ vpnFirstEnabled: Date?)
     }
 
     public enum RegistrationKeyValidity: Codable {
@@ -131,6 +132,10 @@ public final class VPNSettings {
             Change.setShowInMenuBar(showInMenuBar)
         }.eraseToAnyPublisher()
 
+        let vpnFirstEnabledPublisher = vpnFirstEnabledPublisher.map { vpnFirstEnabled in
+            Change.setVPNFirstEnabled(vpnFirstEnabled)
+        }.eraseToAnyPublisher()
+
         return Publishers.MergeMany(
             connectOnLoginPublisher,
             includeAllNetworksPublisher,
@@ -140,7 +145,8 @@ public final class VPNSettings {
             serverChangePublisher,
             locationChangePublisher,
             environmentChangePublisher,
-            showInMenuBarPublisher).eraseToAnyPublisher()
+            showInMenuBarPublisher,
+            vpnFirstEnabledPublisher).eraseToAnyPublisher()
     }()
 
     public init(defaults: UserDefaults) {
@@ -163,6 +169,7 @@ public final class VPNSettings {
 
     // MARK: - Applying Changes
 
+    // swiftlint:disable cyclomatic_complexity
     public func apply(change: Change) {
         switch change {
         case .setConnectOnLogin(let connectOnLogin):
@@ -185,8 +192,11 @@ public final class VPNSettings {
             self.selectedEnvironment = selectedEnvironment
         case .setShowInMenuBar(let showInMenuBar):
             self.showInMenuBar = showInMenuBar
+        case .setVPNFirstEnabled(let vpnFirstEnabled):
+            self.vpnFirstEnabled = vpnFirstEnabled
         }
     }
+    // swiftlint:enable cyclomatic_complexity
 
     // MARK: - Connect on Login
 
@@ -375,6 +385,22 @@ public final class VPNSettings {
             }
         }
     }
+
+    // MARK: - First time VPN is enabled
+
+    public var vpnFirstEnabledPublisher: AnyPublisher<Date?, Never> {
+        defaults.vpnFirstEnabledPublisher
+    }
+
+    public var vpnFirstEnabled: Date? {
+        get {
+            defaults.vpnFirstEnabled
+        }
+
+        set {
+            defaults.vpnFirstEnabled = newValue
+        }
+    }
 }
 
-// swiftlint:enable type_body_length
+// swiftlint:enable type_body_length file_length