diff --git a/Meadow.CLI.Core/DeviceManagement/MeadowDeviceManager.cs b/Meadow.CLI.Core/DeviceManagement/MeadowDeviceManager.cs
index 147fed17..f8bacd16 100644
--- a/Meadow.CLI.Core/DeviceManagement/MeadowDeviceManager.cs
+++ b/Meadow.CLI.Core/DeviceManagement/MeadowDeviceManager.cs
@@ -309,7 +309,7 @@ public static async Task<DebuggingServer> CreateDebuggingServer(MeadowSerialDevi
             {
                 attempts++;
                 meadow.AttemptToReconnectToMeadow();
-            } catch (IOException)
+            } catch (Exception ex) when (ex is IOException || ex.InnerException is IOException)
             {
                 if (attempts < 5)
                 {