diff --git a/packages/flutter_tools/lib/src/runner/target_devices.dart b/packages/flutter_tools/lib/src/runner/target_devices.dart
index a639096bd9..92e802e89a 100644
--- a/packages/flutter_tools/lib/src/runner/target_devices.dart
+++ b/packages/flutter_tools/lib/src/runner/target_devices.dart
@@ -29,7 +29,9 @@ String _foundSpecifiedDevicesMessage(int count, String deviceId) =>
 String _noMatchingDeviceMessage(String deviceId) => 'No supported devices found with name or id '
     "matching '$deviceId'.";
 String flutterSpecifiedDeviceDevModeDisabled(String deviceName) => 'To use '
-    "'$deviceName' for development, enable Developer Mode in Settings → Privacy & Security.";
+    "'$deviceName' for development, enable Developer Mode in Settings → Privacy & Security on the device. "
+    'If this does not work, open Xcode, reconnect the device, and look for a '
+    'popup on the device asking you to trust this computer.';
 String flutterSpecifiedDeviceUnpaired(String deviceName) => "'$deviceName' is not paired. "
     'Open Xcode and trust this computer when prompted.';
 
diff --git a/packages/flutter_tools/test/general.shard/runner/target_devices_test.dart b/packages/flutter_tools/test/general.shard/runner/target_devices_test.dart
index 5e5add9670..184d79a3db 100644
--- a/packages/flutter_tools/test/general.shard/runner/target_devices_test.dart
+++ b/packages/flutter_tools/test/general.shard/runner/target_devices_test.dart
@@ -1267,8 +1267,8 @@ target-device (mobile) • xxx • ios • iOS 16 (unsupported)
 
           final List<Device>? devices = await targetDevices.findAllTargetDevices();
 
-          expect(logger.statusText, equals('''
-To use 'target-device' for development, enable Developer Mode in Settings → Privacy & Security.
+          expect(logger.statusText, equals(r'''
+To use 'target-device' for development, enable Developer Mode in Settings → Privacy & Security on the device. If this does not work, open Xcode, reconnect the device, and look for a popup on the device asking you to trust this computer.
 '''));
           expect(devices, isNull);
         });
@@ -1279,7 +1279,7 @@ To use 'target-device' for development, enable Developer Mode in Settings → Pr
 
           final List<Device>? devices = await targetDevices.findAllTargetDevices();
           expect(logger.statusText, equals('''
-To use 'target-device-1' for development, enable Developer Mode in Settings → Privacy & Security.
+To use 'target-device-1' for development, enable Developer Mode in Settings → Privacy & Security on the device. If this does not work, open Xcode, reconnect the device, and look for a popup on the device asking you to trust this computer.
 Checking for wireless devices...
 '''));
           expect(devices, isNotNull);
@@ -1292,8 +1292,8 @@ Checking for wireless devices...
           final List<Device>? devices = await targetDevices.findAllTargetDevices();
 
           expect(logger.statusText, equals('''
-To use 'target-device-1' for development, enable Developer Mode in Settings → Privacy & Security.
-To use 'target-device-2' for development, enable Developer Mode in Settings → Privacy & Security.
+To use 'target-device-1' for development, enable Developer Mode in Settings → Privacy & Security on the device. If this does not work, open Xcode, reconnect the device, and look for a popup on the device asking you to trust this computer.
+To use 'target-device-2' for development, enable Developer Mode in Settings → Privacy & Security on the device. If this does not work, open Xcode, reconnect the device, and look for a popup on the device asking you to trust this computer.
 No devices found yet. Checking for wireless devices...
 
 No supported devices found with name or id matching 'target-device'.