Prevent iOS from stopping the tunnel if it remains in connecting state for too long

16 files changed, 142 insertions, 229 deletions

diff --git a/ios/MullvadVPN.xcodeproj/project.pbxproj b/ios/MullvadVPN.xcodeproj/project.pbxproj
index 5cb501c04d..8a12966bce 100644
--- a/ios/MullvadVPN.xcodeproj/project.pbxproj
+++ b/ios/MullvadVPN.xcodeproj/project.pbxproj
@@ -273,8 +273,6 @@
 		58C7A4702A8649ED0060C66F /* PingerTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 58C7A46F2A8649ED0060C66F /* PingerTests.swift */; };
 		58C7AF112ABD8480007EDD7A /* TunnelProviderMessage.swift in Sources */ = {isa = PBXBuildFile; fileRef = 585DA89226B0323E00B8C587 /* TunnelProviderMessage.swift */; };
 		58C7AF122ABD8480007EDD7A /* TunnelProviderReply.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5898D2A7290182B000EB5EBA /* TunnelProviderReply.swift */; };
-		58C7AF132ABD8480007EDD7A /* PacketTunnelStatus.swift in Sources */ = {isa = PBXBuildFile; fileRef = 585DA89826B0329200B8C587 /* PacketTunnelStatus.swift */; };
-		58C7AF152ABD8480007EDD7A /* PacketTunnelRelay.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5898D2B62902A9EA00EB5EBA /* PacketTunnelRelay.swift */; };
 		58C7AF162ABD84A8007EDD7A /* URLRequestProxy.swift in Sources */ = {isa = PBXBuildFile; fileRef = 58D229B6298D1D5200BB5A2D /* URLRequestProxy.swift */; };
 		58C7AF172ABD84AA007EDD7A /* ProxyURLRequest.swift in Sources */ = {isa = PBXBuildFile; fileRef = 063687AF28EB083800BE7161 /* ProxyURLRequest.swift */; };
 		58C7AF182ABD84AB007EDD7A /* ProxyURLResponse.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5898D2AD290185D200EB5EBA /* ProxyURLResponse.swift */; };
@@ -1268,7 +1266,6 @@
 		585CA70E25F8C44600B47C62 /* UIMetrics.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = UIMetrics.swift; sourceTree = "<group>"; };
 		585DA87626B024A600B8C587 /* CachedRelays.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = CachedRelays.swift; sourceTree = "<group>"; };
 		585DA89226B0323E00B8C587 /* TunnelProviderMessage.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = TunnelProviderMessage.swift; sourceTree = "<group>"; };
-		585DA89826B0329200B8C587 /* PacketTunnelStatus.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = PacketTunnelStatus.swift; sourceTree = "<group>"; };
 		585E820227F3285E00939F0E /* SendStoreReceiptOperation.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SendStoreReceiptOperation.swift; sourceTree = "<group>"; };
 		58607A4C2947287800BC467D /* AccountExpiryInAppNotificationProvider.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AccountExpiryInAppNotificationProvider.swift; sourceTree = "<group>"; };
 		586168682976F6BD00EF8598 /* DisplayError.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = DisplayError.swift; sourceTree = "<group>"; };
@@ -1358,7 +1355,6 @@
 		5898D2AD290185D200EB5EBA /* ProxyURLResponse.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ProxyURLResponse.swift; sourceTree = "<group>"; };
 		5898D2AF2902A67C00EB5EBA /* RelayLocation.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = RelayLocation.swift; sourceTree = "<group>"; };
 		5898D2B12902A6DE00EB5EBA /* RelayConstraint.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = RelayConstraint.swift; sourceTree = "<group>"; };
-		5898D2B62902A9EA00EB5EBA /* PacketTunnelRelay.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = PacketTunnelRelay.swift; sourceTree = "<group>"; };
 		589A455228E094B300565204 /* OperationsTests.xctest */ = {isa = PBXFileReference; explicitFileType = wrapper.cfbundle; includeInIndex = 0; path = OperationsTests.xctest; sourceTree = BUILT_PRODUCTS_DIR; };
 		589C6A7A2A45ACCA00DAD3EF /* Info.plist */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = text.plist.xml; path = Info.plist; sourceTree = "<group>"; };
 		589C6A7B2A45AE0100DAD3EF /* TunnelObfuscation.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; path = TunnelObfuscation.h; sourceTree = "<group>"; };
@@ -2599,8 +2595,6 @@
 			children = (
 				7AEF7F192AD00F52006FE45D /* AppMessageHandler.swift */,
 				587C575226D2615F005EF767 /* PacketTunnelOptions.swift */,
-				5898D2B62902A9EA00EB5EBA /* PacketTunnelRelay.swift */,
-				585DA89826B0329200B8C587 /* PacketTunnelStatus.swift */,
 				585DA89226B0323E00B8C587 /* TunnelProviderMessage.swift */,
 				5898D2A7290182B000EB5EBA /* TunnelProviderReply.swift */,
 			);
@@ -4206,7 +4200,6 @@
 				58C7AF112ABD8480007EDD7A /* TunnelProviderMessage.swift in Sources */,
 				58C7AF162ABD84A8007EDD7A /* URLRequestProxy.swift in Sources */,
 				58FE25D72AA72A8F003D1918 /* State.swift in Sources */,
-				58C7AF132ABD8480007EDD7A /* PacketTunnelStatus.swift in Sources */,
 				58C7A4592A863FB90060C66F /* WgStats.swift in Sources */,
 				7AD0AA1F2AD6C8B900119E10 /* URLRequestProxyProtocol.swift in Sources */,
 				7A6B4F592AB8412E00123853 /* TunnelMonitorTimings.swift in Sources */,
@@ -4223,7 +4216,6 @@
 				58342C042AAB61FB003BA12D /* State+Extensions.swift in Sources */,
 				583832272AC3193600EA2071 /* PacketTunnelActor+SleepCycle.swift in Sources */,
 				58FE25DC2AA72A8F003D1918 /* AnyTask.swift in Sources */,
-				58C7AF152ABD8480007EDD7A /* PacketTunnelRelay.swift in Sources */,
 				58FE25D92AA72A8F003D1918 /* AutoCancellingTask.swift in Sources */,
 				58FE25E12AA72A9B003D1918 /* SettingsReaderProtocol.swift in Sources */,
 				58C7A4582A863FB90060C66F /* TunnelMonitorProtocol.swift in Sources */,
diff --git a/ios/MullvadVPN/SimulatorTunnelProvider/SimulatorTunnelProviderHost.swift b/ios/MullvadVPN/SimulatorTunnelProvider/SimulatorTunnelProviderHost.swift
index d09a3e94ab..eb3e590fbe 100644
--- a/ios/MullvadVPN/SimulatorTunnelProvider/SimulatorTunnelProviderHost.swift
+++ b/ios/MullvadVPN/SimulatorTunnelProvider/SimulatorTunnelProviderHost.swift
@@ -20,6 +20,7 @@ import RelayCache
 import RelaySelector
 
 final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
+    private var observedState: ObservedState = .disconnected
     private var selectedRelay: SelectedRelay?
     private let urlRequestProxy: URLRequestProxy
     private let relayCacheTracker: RelayCacheTracker
@@ -39,7 +40,12 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
         options: [String: NSObject]?,
         completionHandler: @escaping (Error?) -> Void
     ) {
-        dispatchQueue.async {
+        dispatchQueue.async { [weak self] in
+            guard let self else {
+                completionHandler(nil)
+                return
+            }
+
             var selectedRelay: SelectedRelay?
 
             do {
@@ -47,7 +53,7 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
 
                 selectedRelay = try tunnelOptions.getSelectedRelay()
             } catch {
-                self.providerLogger.error(
+                providerLogger.error(
                     error: error,
                     message: """
                     Failed to decode selected relay passed from the app. \
@@ -57,11 +63,10 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
             }
 
             do {
-                self.selectedRelay = try selectedRelay ?? self.pickRelay()
-
+                setInternalStateConnected(with: try selectedRelay ?? pickRelay())
                 completionHandler(nil)
             } catch {
-                self.providerLogger.error(
+                providerLogger.error(
                     error: error,
                     message: "Failed to pick relay."
                 )
@@ -71,8 +76,9 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
     }
 
     override func stopTunnel(with reason: NEProviderStopReason, completionHandler: @escaping () -> Void) {
-        dispatchQueue.async {
-            self.selectedRelay = nil
+        dispatchQueue.async { [weak self] in
+            self?.selectedRelay = nil
+            self?.observedState = .disconnected
 
             completionHandler()
         }
@@ -98,12 +104,9 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
     private func handleProviderMessage(_ message: TunnelProviderMessage, completionHandler: ((Data?) -> Void)?) {
         switch message {
         case .getTunnelStatus:
-            var tunnelStatus = PacketTunnelStatus()
-            tunnelStatus.tunnelRelay = self.selectedRelay?.packetTunnelRelay
-
             var reply: Data?
             do {
-                reply = try TunnelProviderReply(tunnelStatus).encode()
+                reply = try TunnelProviderReply(observedState).encode()
             } catch {
                 self.providerLogger.error(
                     error: error,
@@ -115,6 +118,7 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
 
         case let .reconnectTunnel(nextRelay):
             reasserting = true
+
             switch nextRelay {
             case let .preSelected(selectedRelay):
                 self.selectedRelay = selectedRelay
@@ -125,7 +129,10 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
             case .current:
                 break
             }
+
+            setInternalStateConnected(with: selectedRelay)
             reasserting = false
+
             completionHandler?(nil)
 
         case let .sendURLRequest(proxyRequest):
@@ -166,6 +173,26 @@ final class SimulatorTunnelProviderHost: SimulatorTunnelProviderDelegate {
             location: selectorResult.location
         )
     }
+
+    private func setInternalStateConnected(with selectedRelay: SelectedRelay?) {
+        guard let selectedRelay = selectedRelay else { return }
+
+        do {
+            observedState = .connected(
+                ObservedConnectionState(
+                    selectedRelay: selectedRelay,
+                    relayConstraints: try SettingsManager.readSettings().relayConstraints,
+                    networkReachability: .reachable,
+                    connectionAttemptCount: 0
+                )
+            )
+        } catch {
+            providerLogger.error(
+                error: error,
+                message: "Failed to read device settings."
+            )
+        }
+    }
 }
 
 #endif
diff --git a/ios/MullvadVPN/TunnelManager/MapConnectionStatusOperation.swift b/ios/MullvadVPN/TunnelManager/MapConnectionStatusOperation.swift
index 5282a2a7d5..d753f5e762 100644
--- a/ios/MullvadVPN/TunnelManager/MapConnectionStatusOperation.swift
+++ b/ios/MullvadVPN/TunnelManager/MapConnectionStatusOperation.swift
@@ -46,30 +46,25 @@ class MapConnectionStatusOperation: AsyncOperation {
         let tunnelState = interactor.tunnelStatus.state
 
         switch connectionStatus {
-        case .connecting:
-            handleConnectingState(tunnelState, tunnel)
-            return
-
-        case .reasserting:
-            fetchTunnelStatus(tunnel: tunnel) { packetTunnelStatus in
-                if let blockedStateReason = packetTunnelStatus.blockedStateReason {
-                    return .error(blockedStateReason)
-                } else if packetTunnelStatus.isNetworkReachable {
-                    return packetTunnelStatus.tunnelRelay.map { .reconnecting($0) }
-                } else {
-                    return .waitingForConnectivity(.noConnection)
-                }
-            }
-            return
-
-        case .connected:
-            fetchTunnelStatus(tunnel: tunnel) { packetTunnelStatus in
-                if let blockedStateReason = packetTunnelStatus.blockedStateReason {
-                    return .error(blockedStateReason)
-                } else if packetTunnelStatus.isNetworkReachable {
-                    return packetTunnelStatus.tunnelRelay.map { .connected($0) }
-                } else {
-                    return .waitingForConnectivity(.noConnection)
+        case .connecting, .reasserting, .connected:
+            fetchTunnelStatus(tunnel: tunnel) { observedState in
+                switch observedState {
+                case let .connected(connectionState):
+                    return connectionState.isNetworkReachable
+                        ? .connected(connectionState.selectedRelay)
+                        : .waitingForConnectivity(.noConnection)
+                case let .connecting(connectionState):
+                    return connectionState.isNetworkReachable
+                        ? .connecting(connectionState.selectedRelay)
+                        : .waitingForConnectivity(.noConnection)
+                case let .reconnecting(connectionState):
+                    return connectionState.isNetworkReachable
+                        ? .reconnecting(connectionState.selectedRelay)
+                        : .waitingForConnectivity(.noConnection)
+                case let .error(blockedState):
+                    return .error(blockedState.reason)
+                case .initial, .disconnecting, .disconnected:
+                    return .none
                 }
             }
             return
@@ -78,7 +73,7 @@ class MapConnectionStatusOperation: AsyncOperation {
             handleDisconnectedState(tunnelState)
 
         case .disconnecting:
-            handleDisconnectionState(tunnelState)
+            handleDisconnectingState(tunnelState)
 
         case .invalid:
             setTunnelDisconnectedStatus()
@@ -94,38 +89,16 @@ class MapConnectionStatusOperation: AsyncOperation {
         request?.cancel()
     }
 
-    private func handleConnectingState(_ tunnelState: TunnelState, _ tunnel: any TunnelProtocol) {
-        switch tunnelState {
-        case .connecting:
-            break
-
-        default:
-            interactor.updateTunnelStatus { tunnelStatus in
-                tunnelStatus.state = .connecting(nil)
-            }
-        }
-
-        fetchTunnelStatus(tunnel: tunnel) { packetTunnelStatus in
-            if let blockedStateReason = packetTunnelStatus.blockedStateReason {
-                return .error(blockedStateReason)
-            } else if packetTunnelStatus.isNetworkReachable {
-                return packetTunnelStatus.tunnelRelay.map { .connecting($0) }
-            } else {
-                return .waitingForConnectivity(.noConnection)
-            }
-        }
-    }
-
-    private func handleDisconnectionState(_ tunnelState: TunnelState) {
+    private func handleDisconnectingState(_ tunnelState: TunnelState) {
         switch tunnelState {
         case .disconnecting:
             break
         default:
             interactor.updateTunnelStatus { tunnelStatus in
-                let packetTunnelStatus = tunnelStatus.packetTunnelStatus
+                let isNetworkReachable = tunnelStatus.observedState.connectionState?.isNetworkReachable ?? false
 
                 tunnelStatus = TunnelStatus()
-                tunnelStatus.state = packetTunnelStatus.isNetworkReachable
+                tunnelStatus.state = isNetworkReachable
                     ? .disconnecting(.nothing)
                     : .waitingForConnectivity(.noNetwork)
             }
@@ -161,17 +134,17 @@ class MapConnectionStatusOperation: AsyncOperation {
 
     private func fetchTunnelStatus(
         tunnel: any TunnelProtocol,
-        mapToState: @escaping (PacketTunnelStatus) -> TunnelState?
+        mapToState: @escaping (ObservedState) -> TunnelState?
     ) {
-        request = tunnel.getTunnelStatus { [weak self] completion in
+        request = tunnel.getTunnelStatus { [weak self] result in
             guard let self else { return }
 
             dispatchQueue.async {
-                if case let .success(packetTunnelStatus) = completion, !self.isCancelled {
+                if case let .success(observedState) = result, !self.isCancelled {
                     self.interactor.updateTunnelStatus { tunnelStatus in
-                        tunnelStatus.packetTunnelStatus = packetTunnelStatus
+                        tunnelStatus.observedState = observedState
 
-                        if let newState = mapToState(packetTunnelStatus) {
+                        if let newState = mapToState(observedState) {
                             tunnelStatus.state = newState
                         }
                     }
diff --git a/ios/MullvadVPN/TunnelManager/StartTunnelOperation.swift b/ios/MullvadVPN/TunnelManager/StartTunnelOperation.swift
index 525dade2cd..5f4aa8ec51 100644
--- a/ios/MullvadVPN/TunnelManager/StartTunnelOperation.swift
+++ b/ios/MullvadVPN/TunnelManager/StartTunnelOperation.swift
@@ -91,8 +91,7 @@ class StartTunnelOperation: ResultOperation<Void> {
 
         interactor.updateTunnelStatus { tunnelStatus in
             tunnelStatus = TunnelStatus()
-            tunnelStatus.packetTunnelStatus.tunnelRelay = selectedRelay?.packetTunnelRelay
-            tunnelStatus.state = .connecting(selectedRelay?.packetTunnelRelay)
+            tunnelStatus.state = .connecting(selectedRelay)
         }
 
         try tunnel.start(options: tunnelOptions.rawOptions())
diff --git a/ios/MullvadVPN/TunnelManager/Tunnel+Messaging.swift b/ios/MullvadVPN/TunnelManager/Tunnel+Messaging.swift
index 044901c37d..a553b0d0af 100644
--- a/ios/MullvadVPN/TunnelManager/Tunnel+Messaging.swift
+++ b/ios/MullvadVPN/TunnelManager/Tunnel+Messaging.swift
@@ -43,7 +43,7 @@ extension TunnelProtocol {
 
     /// Request status from packet tunnel process.
     func getTunnelStatus(
-        completionHandler: @escaping (Result<PacketTunnelStatus, Error>) -> Void
+        completionHandler: @escaping (Result<ObservedState, Error>) -> Void
     ) -> Cancellable {
         let operation = SendTunnelProviderMessageOperation(
             dispatchQueue: dispatchQueue,
diff --git a/ios/MullvadVPN/TunnelManager/TunnelManager.swift b/ios/MullvadVPN/TunnelManager/TunnelManager.swift
index e35827e114..0f32bf0512 100644
--- a/ios/MullvadVPN/TunnelManager/TunnelManager.swift
+++ b/ios/MullvadVPN/TunnelManager/TunnelManager.swift
@@ -696,7 +696,7 @@ final class TunnelManager: StorePaymentObserver {
 
         // Packet tunnel may have attempted or rotated the key.
         // In that case we have to reload device state from Keychain as it's likely was modified by packet tunnel.
-        let newPacketTunnelKeyRotation = newTunnelStatus.packetTunnelStatus.lastKeyRotation
+        let newPacketTunnelKeyRotation = newTunnelStatus.observedState.connectionState?.lastKeyRotation
         if lastPacketTunnelKeyRotation != newPacketTunnelKeyRotation {
             lastPacketTunnelKeyRotation = newPacketTunnelKeyRotation
             refreshDeviceState()
@@ -816,7 +816,7 @@ final class TunnelManager: StorePaymentObserver {
         let selectorResult = try RelaySelector.evaluate(
             relays: cachedRelays.relays,
             constraints: settings.relayConstraints,
-            numberOfFailedAttempts: tunnelStatus.packetTunnelStatus.numberOfFailedAttempts
+            numberOfFailedAttempts: tunnelStatus.observedState.connectionState?.connectionAttemptCount ?? 0
         )
 
         return SelectedRelay(
diff --git a/ios/MullvadVPN/TunnelManager/TunnelState.swift b/ios/MullvadVPN/TunnelManager/TunnelState.swift
index aed7fb2cc2..877046cac8 100644
--- a/ios/MullvadVPN/TunnelManager/TunnelState.swift
+++ b/ios/MullvadVPN/TunnelManager/TunnelState.swift
@@ -13,7 +13,7 @@ import PacketTunnelCore
 /// A struct describing the tunnel status.
 struct TunnelStatus: Equatable, CustomStringConvertible {
     /// Tunnel status returned by tunnel process.
-    var packetTunnelStatus = PacketTunnelStatus()
+    var observedState: ObservedState = .disconnected
 
     /// Tunnel state.
     var state: TunnelState = .disconnected
@@ -21,10 +21,14 @@ struct TunnelStatus: Equatable, CustomStringConvertible {
     var description: String {
         var s = "\(state), network "
 
-        if packetTunnelStatus.isNetworkReachable {
-            s += "reachable"
+        if let connectionState = observedState.connectionState {
+            if connectionState.isNetworkReachable {
+                s += "reachable"
+            } else {
+                s += "unreachable"
+            }
         } else {
-            s += "unreachable"
+            s += "reachability unknown"
         }
 
         return s
@@ -44,10 +48,10 @@ enum TunnelState: Equatable, CustomStringConvertible {
     case pendingReconnect
 
     /// Connecting the tunnel.
-    case connecting(PacketTunnelRelay?)
+    case connecting(SelectedRelay?)
 
     /// Connected the tunnel
-    case connected(PacketTunnelRelay)
+    case connected(SelectedRelay)
 
     /// Disconnecting the tunnel
     case disconnecting(ActionAfterDisconnect)
@@ -60,7 +64,7 @@ enum TunnelState: Equatable, CustomStringConvertible {
     /// 1. Asking the running tunnel to reconnect to new relay via IPC.
     /// 2. Tunnel attempts to reconnect to new relay as the current relay appears to be
     ///    dysfunctional.
-    case reconnecting(PacketTunnelRelay)
+    case reconnecting(SelectedRelay)
 
     /// Waiting for connectivity to come back up.
     case waitingForConnectivity(WaitingForConnectionReason)
@@ -102,7 +106,7 @@ enum TunnelState: Equatable, CustomStringConvertible {
         }
     }
 
-    var relay: PacketTunnelRelay? {
+    var relay: SelectedRelay? {
         switch self {
         case let .connected(relay), let .reconnecting(relay):
             return relay
diff --git a/ios/MullvadVPN/View controllers/Tunnel/TunnelControlView.swift b/ios/MullvadVPN/View controllers/Tunnel/TunnelControlView.swift
index dc6669fb47..4abc59791c 100644
--- a/ios/MullvadVPN/View controllers/Tunnel/TunnelControlView.swift
+++ b/ios/MullvadVPN/View controllers/Tunnel/TunnelControlView.swift
@@ -223,7 +223,7 @@ final class TunnelControlView: UIView {
             )
 
             connectionPanel.dataSource = ConnectionPanelData(
-                inAddress: "\(tunnelRelay.ipv4Relay) UDP",
+                inAddress: "\(tunnelRelay.endpoint.ipv4Relay) UDP",
                 outAddress: nil
             )
             connectionPanel.isHidden = false
diff --git a/ios/PacketTunnel/PacketTunnelProvider/PacketTunnelProvider.swift b/ios/PacketTunnel/PacketTunnelProvider/PacketTunnelProvider.swift
index cf8ec138f7..4754887979 100644
--- a/ios/PacketTunnel/PacketTunnelProvider/PacketTunnelProvider.swift
+++ b/ios/PacketTunnel/PacketTunnelProvider/PacketTunnelProvider.swift
@@ -100,7 +100,21 @@ class PacketTunnelProvider: NEPacketTunnelProvider {
 
         actor.start(options: startOptions)
 
-        await actor.waitUntilConnected()
+        for await state in await actor.observedStates {
+            switch state {
+            case .connected, .disconnected, .error:
+                return
+            case let .connecting(connectionState):
+                // Give the tunnel a few tries to connect, otherwise return immediately. This will enable VPN in
+                // device settings, but the app will still report the true state via ObservedState over IPC.
+                // In essence, this prevents the 60s tunnel timeout to trigger.
+                if connectionState.connectionAttemptCount > 1 {
+                    return
+                }
+            default:
+                break
+            }
+        }
     }
 
     override func stopTunnel(with reason: NEProviderStopReason) async {
diff --git a/ios/PacketTunnelCore/Actor/ObservedState+Extensions.swift b/ios/PacketTunnelCore/Actor/ObservedState+Extensions.swift
index 954f4450c5..05624a6565 100644
--- a/ios/PacketTunnelCore/Actor/ObservedState+Extensions.swift
+++ b/ios/PacketTunnelCore/Actor/ObservedState+Extensions.swift
@@ -10,37 +10,6 @@ import Foundation
 import MullvadTypes
 
 extension ObservedState {
-    public var packetTunnelStatus: PacketTunnelStatus {
-        var status = PacketTunnelStatus()
-
-        switch self {
-        case let .connecting(connState),
-             let .connected(connState),
-             let .reconnecting(connState),
-             let .disconnecting(connState):
-            switch connState.networkReachability {
-            case .reachable:
-                status.isNetworkReachable = true
-            case .unreachable:
-                status.isNetworkReachable = false
-            case .undetermined:
-                // TODO: fix me
-                status.isNetworkReachable = true
-            }
-
-            status.numberOfFailedAttempts = connState.connectionAttemptCount
-            status.tunnelRelay = connState.selectedRelay.packetTunnelRelay
-
-        case .disconnected, .initial:
-            break
-
-        case let .error(blockedState):
-            status.blockedStateReason = blockedState.reason
-        }
-
-        return status
-    }
-
     public var relayConstraints: RelayConstraints? {
         switch self {
         case let .connecting(connState), let .connected(connState), let .reconnecting(connState):
@@ -72,4 +41,26 @@ extension ObservedState {
             return "Error"
         }
     }
+
+    public var connectionState: ObservedConnectionState? {
+        switch self {
+        case
+            let .connecting(connectionState),
+            let .reconnecting(connectionState),
+            let .connected(connectionState),
+            let .disconnecting(connectionState):
+            connectionState
+        default:
+            nil
+        }
+    }
+
+    public var blockedState: ObservedBlockedState? {
+        switch self {
+        case let .error(blockedState):
+            blockedState
+        default:
+            nil
+        }
+    }
 }
diff --git a/ios/PacketTunnelCore/Actor/ObservedState.swift b/ios/PacketTunnelCore/Actor/ObservedState.swift
index bdef364122..01f31e9abd 100644
--- a/ios/PacketTunnelCore/Actor/ObservedState.swift
+++ b/ios/PacketTunnelCore/Actor/ObservedState.swift
@@ -28,6 +28,25 @@ public struct ObservedConnectionState: Equatable, Codable {
     public var relayConstraints: RelayConstraints
     public var networkReachability: NetworkReachability
     public var connectionAttemptCount: UInt
+    public var lastKeyRotation: Date?
+
+    public var isNetworkReachable: Bool {
+        networkReachability != .unreachable
+    }
+
+    public init(
+        selectedRelay: SelectedRelay,
+        relayConstraints: RelayConstraints,
+        networkReachability: NetworkReachability,
+        connectionAttemptCount: UInt,
+        lastKeyRotation: Date? = nil
+    ) {
+        self.selectedRelay = selectedRelay
+        self.relayConstraints = relayConstraints
+        self.networkReachability = networkReachability
+        self.connectionAttemptCount = connectionAttemptCount
+        self.lastKeyRotation = lastKeyRotation
+    }
 }
 
 /// A serializable representation of internal blocked state.
@@ -65,7 +84,8 @@ extension ConnectionState {
             selectedRelay: selectedRelay,
             relayConstraints: relayConstraints,
             networkReachability: networkReachability,
-            connectionAttemptCount: connectionAttemptCount
+            connectionAttemptCount: connectionAttemptCount,
+            lastKeyRotation: lastKeyRotation
         )
     }
 }
diff --git a/ios/PacketTunnelCore/Actor/PacketTunnelActor+Extensions.swift b/ios/PacketTunnelCore/Actor/PacketTunnelActor+Extensions.swift
index 3bd2c56315..3610c3ff50 100644
--- a/ios/PacketTunnelCore/Actor/PacketTunnelActor+Extensions.swift
+++ b/ios/PacketTunnelCore/Actor/PacketTunnelActor+Extensions.swift
@@ -28,21 +28,6 @@ extension PacketTunnelActor {
         }
     }
 
-    /// Wait until the `observedState` moved to `.connected`.
-    /// Should return if the state is `.disconnected` as this is the final state of actor.
-    public func waitUntilConnected() async {
-        for await newState in observedStates {
-            switch newState {
-            case .connected, .disconnected:
-                // Return once either desired or final state is reached.
-                return
-
-            case .connecting, .disconnecting, .error, .initial, .reconnecting:
-                break
-            }
-        }
-    }
-
     /// Wait until the `observedState` moved to `.disiconnected`.
     public func waitUntilDisconnected() async {
         for await newState in observedStates {
diff --git a/ios/PacketTunnelCore/Actor/Protocols/RelaySelectorProtocol.swift b/ios/PacketTunnelCore/Actor/Protocols/RelaySelectorProtocol.swift
index 8127008a8f..7cd3003537 100644
--- a/ios/PacketTunnelCore/Actor/Protocols/RelaySelectorProtocol.swift
+++ b/ios/PacketTunnelCore/Actor/Protocols/RelaySelectorProtocol.swift
@@ -32,15 +32,3 @@ public struct SelectedRelay: Equatable, Codable {
         self.location = location
     }
 }
-
-extension SelectedRelay {
-    /// Converts `SelectedRelay` to `PacketTunnelRelay` for sharing with UI.
-    public var packetTunnelRelay: PacketTunnelRelay {
-        PacketTunnelRelay(
-            ipv4Relay: endpoint.ipv4Relay,
-            ipv6Relay: endpoint.ipv6Relay,
-            hostname: hostname,
-            location: location
-        )
-    }
-}
diff --git a/ios/PacketTunnelCore/IPC/AppMessageHandler.swift b/ios/PacketTunnelCore/IPC/AppMessageHandler.swift
index 4ad557f7ba..3a852660e1 100644
--- a/ios/PacketTunnelCore/IPC/AppMessageHandler.swift
+++ b/ios/PacketTunnelCore/IPC/AppMessageHandler.swift
@@ -47,7 +47,7 @@ public struct AppMessageHandler {
             return nil
 
         case .getTunnelStatus:
-            return await encodeReply(packetTunnelActor.observedState.packetTunnelStatus)
+            return await encodeReply(packetTunnelActor.observedState)
 
         case .privateKeyRotation:
             packetTunnelActor.notifyKeyRotation(date: Date())
diff --git a/ios/PacketTunnelCore/IPC/PacketTunnelRelay.swift b/ios/PacketTunnelCore/IPC/PacketTunnelRelay.swift
deleted file mode 100644
index 4f69837240..0000000000
--- a/ios/PacketTunnelCore/IPC/PacketTunnelRelay.swift
+++ /dev/null
@@ -1,37 +0,0 @@
-//
-//  PacketTunnelRelay.swift
-//  PacketTunnelCore
-//
-//  Created by pronebird on 21/10/2022.
-//  Copyright © 2022 Mullvad VPN AB. All rights reserved.
-//
-
-import Foundation
-import MullvadTypes
-
-/// Struct holding tunnel relay information.
-public struct PacketTunnelRelay: Codable, Equatable {
-    /// IPv4 relay endpoint.
-    public let ipv4Relay: IPv4Endpoint
-
-    /// IPv6 relay endpoint.
-    public let ipv6Relay: IPv6Endpoint?
-
-    /// Relay hostname.
-    public let hostname: String
-
-    /// Relay location.
-    public let location: Location
-
-    public init(
-        ipv4Relay: IPv4Endpoint,
-        ipv6Relay: IPv6Endpoint? = nil,
-        hostname: String,
-        location: Location
-    ) {
-        self.ipv4Relay = ipv4Relay
-        self.ipv6Relay = ipv6Relay
-        self.hostname = hostname
-        self.location = location
-    }
-}
diff --git a/ios/PacketTunnelCore/IPC/PacketTunnelStatus.swift b/ios/PacketTunnelCore/IPC/PacketTunnelStatus.swift
deleted file mode 100644
index f18f551037..0000000000
--- a/ios/PacketTunnelCore/IPC/PacketTunnelStatus.swift
+++ /dev/null
@@ -1,43 +0,0 @@
-//
-//  PacketTunnelStatus.swift
-//  PacketTunnelCore
-//
-//  Created by pronebird on 27/07/2021.
-//  Copyright © 2021 Mullvad VPN AB. All rights reserved.
-//
-
-import Foundation
-import MullvadTypes
-
-/// Struct describing packet tunnel process status.
-public struct PacketTunnelStatus: Codable, Equatable {
-    /// The reason why packet tunnel entered error state.
-    /// Set to `nil` when tunnel is not in error state.
-    public var blockedStateReason: BlockedStateReason?
-
-    /// Flag indicating whether network is reachable.
-    public var isNetworkReachable: Bool
-
-    /// The date of last performed key rotation during device check.
-    public var lastKeyRotation: Date?
-
-    /// Current relay.
-    public var tunnelRelay: PacketTunnelRelay?
-
-    /// Number of consecutive connection failure attempts.
-    public var numberOfFailedAttempts: UInt
-
-    public init(
-        blockStateReason: BlockedStateReason? = nil,
-        isNetworkReachable: Bool = true,
-        lastKeyRotation: Date? = nil,
-        tunnelRelay: PacketTunnelRelay? = nil,
-        numberOfFailedAttempts: UInt = 0
-    ) {
-        self.blockedStateReason = blockStateReason
-        self.isNetworkReachable = isNetworkReachable
-        self.lastKeyRotation = lastKeyRotation
-        self.tunnelRelay = tunnelRelay
-        self.numberOfFailedAttempts = numberOfFailedAttempts
-    }
-}