diff --git a/arduino-core/src/processing/app/debug/Compiler.java b/arduino-core/src/processing/app/debug/Compiler.java
index 0c5ec8057..9a684a3a1 100644
--- a/arduino-core/src/processing/app/debug/Compiler.java
+++ b/arduino-core/src/processing/app/debug/Compiler.java
@@ -182,7 +182,14 @@ public class Compiler implements MessageConsumer {
   }
 
   static public File findCompiledSketch(PreferencesMap prefs) throws PreferencesMapException {
-    List<String> paths = Arrays.asList("{build.path}/{build.project_name}.hex", "{build.path}/{build.project_name}.bin");
+    List<String> paths = Arrays.asList(
+      "{build.path}/sketch/{build.project_name}.with_bootloader.hex",
+      "{build.path}/sketch/{build.project_name}.hex",
+      "{build.path}/{build.project_name}.with_bootloader.hex",
+      "{build.path}/{build.project_name}.hex",
+      "{build.path}/sketch/{build.project_name}.bin",
+      "{build.path}/{build.project_name}.bin"
+    );
     Optional<File> sketch = paths.stream().
       map(path -> StringReplacer.replaceFromMapping(path, prefs)).
       map(File::new).