diff --git a/ios/NebulaNetworkExtension/PacketTunnelProvider.swift b/ios/NebulaNetworkExtension/PacketTunnelProvider.swift
index 9f3ae8c..61e131a 100644
--- a/ios/NebulaNetworkExtension/PacketTunnelProvider.swift
+++ b/ios/NebulaNetworkExtension/PacketTunnelProvider.swift
@@ -13,15 +13,12 @@ class PacketTunnelProvider: NEPacketTunnelProvider {
     private var didSleep = false
     private var cachedRouteDescription: String?
     
-    // This is the system completionHandler, only set when we expect the UI to ask us to actually start so that errors can flow back to the UI
-    private var startCompleter: ((Error?) -> Void)?
-    
-    override func startTunnel(options: [String : NSObject]?, completionHandler: @escaping (Error?) -> Void) {       
+    override func startTunnel(options: [String : NSObject]?, completionHandler: @escaping (Error?) -> Void) {
         // There is currently no way to get initialization errors back to the UI via completionHandler here
         // `expectStart` is sent only via the UI which means we should wait for the real start command which has another completion handler the UI can intercept
-        // In the end we need to call this completionHandler to inform the system of our state
         if options?["expectStart"] != nil {
-            startCompleter = completionHandler
+            // The system completion handler must be called before IPC will work
+            completionHandler(nil)
             return
         }
         
@@ -175,19 +172,6 @@ class PacketTunnelProvider: NEPacketTunnelProvider {
         // start command has special treatment due to needing to call two completers
         if call.command == "start" {
             self.start() { error in
-                // Notify the system of our start result
-                if self.startCompleter != nil {
-                    if error == nil {
-                        // Clean boot, no errors
-                        self.startCompleter!(nil)
-                        
-                    } else {
-                        // We encountered an error, we can just pass NSError() here since ios throws it away
-                        // But we will provide it in the event we can intercept the error without doing this workaround sometime in the future
-                        self.startCompleter!(error!.localizedDescription)
-                    }
-                }
-                
                 // Notify the UI if we have a completionHandler
                 if completionHandler != nil {
                     if error == nil {
@@ -195,8 +179,9 @@ class PacketTunnelProvider: NEPacketTunnelProvider {
                         completionHandler!(try? JSONEncoder().encode(IPCResponse.init(type: .success, message: nil)))
                         
                     } else {
-                        // Error response has
+                        // We failed, notify and shutdown
                         completionHandler!(try? JSONEncoder().encode(IPCResponse.init(type: .error, message: JSON(error!.localizedDescription))))
+                        self.cancelTunnelWithError(error)
                     }
                 }
             }
diff --git a/ios/NebulaNetworkExtension/Site.swift b/ios/NebulaNetworkExtension/Site.swift
index 0a5653d..5708850 100644
--- a/ios/NebulaNetworkExtension/Site.swift
+++ b/ios/NebulaNetworkExtension/Site.swift
@@ -97,7 +97,7 @@ struct CertificateValidity: Codable {
 let statusMap: Dictionary<NEVPNStatus, Bool> = [
     NEVPNStatus.invalid: false,
     NEVPNStatus.disconnected: false,
-    NEVPNStatus.connecting: true,
+    NEVPNStatus.connecting: false,
     NEVPNStatus.connected: true,
     NEVPNStatus.reasserting: true,
     NEVPNStatus.disconnecting: true,
diff --git a/ios/Runner/Sites.swift b/ios/Runner/Sites.swift
index ebf2b6e..7a8f79f 100644
--- a/ios/Runner/Sites.swift
+++ b/ios/Runner/Sites.swift
@@ -134,22 +134,22 @@ class SiteUpdater: NSObject, FlutterStreamHandler {
         }
         
         self.notification = NotificationCenter.default.addObserver(forName: NSNotification.Name.NEVPNStatusDidChange, object: site.manager!.connection , queue: nil) { n in
-            let connected = self.site.connected
+            let oldConnected = self.site.connected
             self.site.status = statusString[self.site.manager!.connection.status]
             self.site.connected = statusMap[self.site.manager!.connection.status]
-
+            
             // Check to see if we just moved to connected and if we have a start function to call when that happens
-            if self.site.connected! && connected != self.site.connected && self.startFunc != nil {
+            if self.site.connected! && oldConnected != self.site.connected && self.startFunc != nil {
                 self.startFunc!()
                 self.startFunc = nil
             }
-
+            
             self.update(connected: self.site.connected!)
         }
 #endif
         return nil
     }
-
+    
     /// onCancel is called when the flutter listener stops listening
     func onCancel(withArguments arguments: Any?) -> FlutterError? {
         if (self.notification != nil) {