diff --git a/infection_monkey/main.py b/infection_monkey/main.py
index 6bdef408c..51fd6b9f7 100644
--- a/infection_monkey/main.py
+++ b/infection_monkey/main.py
@@ -91,7 +91,12 @@ def main():
 
     if WormConfiguration.use_file_logging:
         if os.path.exists(log_path):
-            os.remove(log_path)
+            # If log exists but can't be removed it means other monkey is running. This usually happens on upgrade
+            # from 32bit to 64bit monkey on Windows. In all cases this shouldn't be a problem.
+            try:
+                os.remove(log_path)
+            except OSError:
+                pass
         LOG_CONFIG['handlers']['file']['filename'] = log_path
         LOG_CONFIG['root']['handlers'].append('file')
     else: