diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/IPCClient.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/IPCClient.swift
index 25c2d172a..801eca058 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/IPCClient.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/IPCClient.swift
@@ -50,14 +50,24 @@ class IPCClient {
   let decoder = PropertyListDecoder()
 
   // Auto-connect
-  func start() throws {
-    try session().startTunnel(options: nil)
+  @MainActor
+  func start(configuration: Configuration) throws {
+    let tunnelConfiguration = configuration.toTunnelConfiguration()
+    let configData = try encoder.encode(tunnelConfiguration)
+    let options: [String: NSObject] = [
+      "configuration": configData as NSObject
+    ]
+    try session().startTunnel(options: options)
   }
 
   // Sign in
-  func start(token: String) throws {
+  @MainActor
+  func start(token: String, configuration: Configuration) throws {
+    let tunnelConfiguration = configuration.toTunnelConfiguration()
+    let configData = try encoder.encode(tunnelConfiguration)
     let options: [String: NSObject] = [
-      "token": token as NSObject
+      "token": token as NSObject,
+      "configuration": configData as NSObject,
     ]
 
     try session().startTunnel(options: options)
@@ -76,8 +86,14 @@ class IPCClient {
     // On macOS, IPC calls to the system extension won't work after it's been upgraded, until the startTunnel call.
     // Since we rely on IPC for the GUI to function, we need to send a dummy `startTunnel` that doesn't actually
     // start the tunnel, but causes the system to wake the extension.
-    func dryStartStopCycle() throws {
-      let options: [String: NSObject] = ["dryRun": true as NSObject]
+    @MainActor
+    func dryStartStopCycle(configuration: Configuration) throws {
+      let tunnelConfiguration = configuration.toTunnelConfiguration()
+      let configData = try encoder.encode(tunnelConfiguration)
+      let options: [String: NSObject] = [
+        "dryRun": true as NSObject,
+        "configuration": configData as NSObject,
+      ]
       try session().startTunnel(options: options)
     }
   #endif
@@ -87,6 +103,10 @@ class IPCClient {
     let tunnelConfiguration = configuration.toTunnelConfiguration()
     let message = ProviderMessage.setConfiguration(tunnelConfiguration)
 
+    if sessionStatus() != .connected {
+      Log.trace("Not setting configuration whilst not connected")
+      return
+    }
     try await sendMessageWithoutResponse(message)
   }
 
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/Store.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/Store.swift
index 7259d9cf5..81b3ed114 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/Store.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/Store.swift
@@ -193,7 +193,7 @@ public final class Store: ObservableObject {
   private func maybeAutoConnect() async throws {
     if configuration.connectOnStart {
       try await manager().enable()
-      try ipcClient().start()
+      try ipcClient().start(configuration: configuration)
     }
   }
   func installVPNConfiguration() async throws {
@@ -232,7 +232,7 @@ public final class Store: ObservableObject {
       if vpnStatus == .connected || vpnStatus == .connecting || vpnStatus == .reasserting {
         try ipcClient().stop()
       } else {
-        try ipcClient().dryStartStopCycle()
+        try ipcClient().dryStartStopCycle(configuration: configuration)
       }
     #else
       try ipcClient().stop()
@@ -251,14 +251,13 @@ public final class Store: ObservableObject {
     Telemetry.accountSlug = accountSlug
 
     try await manager().enable()
-    try await ipcClient().setConfiguration(configuration)
 
     // Clear shown alerts when starting a new session so user can see new errors
     shownAlertIds.removeAll()
     UserDefaults.standard.removeObject(forKey: "shownAlertIds")
 
-    // Bring the tunnel up and send it a token to start
-    try ipcClient().start(token: authResponse.token)
+    // Bring the tunnel up and send it a token and configuration to start
+    try ipcClient().start(token: authResponse.token, configuration: configuration)
   }
 
   func signOut() async throws {
diff --git a/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift b/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift
index a09659e3a..856409e84 100644
--- a/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift
+++ b/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift
@@ -68,6 +68,20 @@ class PacketTunnelProvider: NEPacketTunnelProvider {
     let build = Bundle.main.object(forInfoDictionaryKey: "CFBundleVersion") as? String ?? "unknown"
     Log.info("Starting tunnel - Version: \(version), Build: \(build)")
 
+    // Try to load configuration from options first (passed from client at startup)
+    if let configData = options?["configuration"] as? Data {
+      do {
+        let decoder = PropertyListDecoder()
+        let configFromOptions = try decoder.decode(TunnelConfiguration.self, from: configData)
+        Log.info("Loaded configuration from startTunnel options")
+        // Save it for future fallback (e.g., system-initiated restarts)
+        configFromOptions.save()
+        self.tunnelConfiguration = configFromOptions
+      } catch {
+        Log.error(error)
+      }
+    }
+
     // If the tunnel starts up before the GUI after an upgrade crossing the 1.4.15 version boundary,
     // the old system settings-based config will still be present and the new configuration will be empty.
     // So handle that edge case gracefully.
diff --git a/swift/apple/FirezoneNetworkExtension/SessionEventLoop.swift b/swift/apple/FirezoneNetworkExtension/SessionEventLoop.swift
index 06cb3f44a..734fb98a2 100644
--- a/swift/apple/FirezoneNetworkExtension/SessionEventLoop.swift
+++ b/swift/apple/FirezoneNetworkExtension/SessionEventLoop.swift
@@ -48,7 +48,9 @@ private func forwardEvents(from session: Session, to eventSender: Sender<Event>)
 }
 
 /// Forwards commands from the command receiver to the session.
-private func forwardCommands(from commandReceiver: Receiver<SessionCommand>, to session: Session) async {
+private func forwardCommands(from commandReceiver: Receiver<SessionCommand>, to session: Session)
+  async
+{
   for await command in commandReceiver.stream {
     if Task.isCancelled {
       Log.log("Command forwarding cancelled")