diff --git a/monkey/infection_monkey/ransomware/ransomware_payload.py b/monkey/infection_monkey/ransomware/ransomware_payload.py
index 7753022ff..e0f9fe7ec 100644
--- a/monkey/infection_monkey/ransomware/ransomware_payload.py
+++ b/monkey/infection_monkey/ransomware/ransomware_payload.py
@@ -56,10 +56,10 @@ class RansomewarePayload:
                 LOG.debug(f"Encrypting {filepath}")
                 self._encryptor.encrypt_file_in_place(filepath)
                 self._add_extension(filepath)
-                self._send_telemetry(filepath, "")
+                self._send_telemetry(filepath, True, "")
             except Exception as ex:
                 LOG.warning(f"Error encrypting {filepath}: {ex}")
-                self._send_telemetry(filepath, str(ex))
+                self._send_telemetry(filepath, False, str(ex))
 
         return results
 
@@ -67,6 +67,6 @@ class RansomewarePayload:
         new_filepath = filepath.with_suffix(f"{filepath.suffix}{self._new_file_extension}")
         filepath.rename(new_filepath)
 
-    def _send_telemetry(self, filepath: Path, error: str):
-        encryption_attempt = FileEncryptionTelem(str(filepath), str(error))
+    def _send_telemetry(self, filepath: Path, success: bool, error: str):
+        encryption_attempt = FileEncryptionTelem(str(filepath), success, error)
         self._telemetry_messenger.send_telemetry(encryption_attempt)
diff --git a/monkey/infection_monkey/telemetry/file_encryption_telem.py b/monkey/infection_monkey/telemetry/file_encryption_telem.py
index 117140f91..ff298d3cc 100644
--- a/monkey/infection_monkey/telemetry/file_encryption_telem.py
+++ b/monkey/infection_monkey/telemetry/file_encryption_telem.py
@@ -7,7 +7,7 @@ from infection_monkey.telemetry.i_batchable_telem import IBatchableTelem
 
 
 class FileEncryptionTelem(BatchableTelemMixin, IBatchableTelem, BaseTelem):
-    def __init__(self, filepath: Path, error: str):
+    def __init__(self, filepath: Path, success: bool, error: str):
         """
         File Encryption telemetry constructor
         :param attempts: List of tuples with each tuple containing the path
@@ -17,7 +17,7 @@ class FileEncryptionTelem(BatchableTelemMixin, IBatchableTelem, BaseTelem):
         """
         super().__init__()
 
-        self._telemetry_entries.append({"path": filepath, "error": error})
+        self._telemetry_entries.append({"path": filepath, "success": success, "error": error})
 
     telem_category = TelemCategoryEnum.FILE_ENCRYPTION
 
diff --git a/monkey/tests/unit_tests/infection_monkey/ransomware/test_ransomware_payload.py b/monkey/tests/unit_tests/infection_monkey/ransomware/test_ransomware_payload.py
index 70c43e8c6..7557c5055 100644
--- a/monkey/tests/unit_tests/infection_monkey/ransomware/test_ransomware_payload.py
+++ b/monkey/tests/unit_tests/infection_monkey/ransomware/test_ransomware_payload.py
@@ -134,8 +134,10 @@ def test_telemetry_success(ransomware_payload, telemetry_messenger_spy):
     telem_2 = telemetry_messenger_spy.telemetries[1]
 
     assert ALL_ZEROS_PDF in telem_1.get_data()["files"][0]["path"]
+    assert telem_1.get_data()["files"][0]["success"]
     assert telem_1.get_data()["files"][0]["error"] == ""
     assert TEST_KEYBOARD_TXT in telem_2.get_data()["files"][0]["path"]
+    assert telem_2.get_data()["files"][0]["success"]
     assert telem_2.get_data()["files"][0]["error"] == ""
 
 
@@ -150,4 +152,5 @@ def test_telemetry_failure(monkeypatch, ransomware_payload, telemetry_messenger_
     telem_1 = telemetry_messenger_spy.telemetries[0]
 
     assert "/file/not/exist" in telem_1.get_data()["files"][0]["path"]
+    assert not telem_1.get_data()["files"][0]["success"]
     assert "No such file or directory" in telem_1.get_data()["files"][0]["error"]
diff --git a/monkey/tests/unit_tests/infection_monkey/telemetry/test_file_encryption_telem.py b/monkey/tests/unit_tests/infection_monkey/telemetry/test_file_encryption_telem.py
index 07dd556dd..b6d55b9d0 100644
--- a/monkey/tests/unit_tests/infection_monkey/telemetry/test_file_encryption_telem.py
+++ b/monkey/tests/unit_tests/infection_monkey/telemetry/test_file_encryption_telem.py
@@ -3,17 +3,21 @@ import json
 from infection_monkey.telemetry.file_encryption_telem import FileEncryptionTelem
 
 ENCRYPTION_ATTEMPTS = [
-    {"path": "<file1>", "error": "<encryption attempt result>"},
-    {"path": "<file2>", "error": ""},
+    {"path": "<file1>", "success": False, "error": "<encryption attempt result>"},
+    {"path": "<file2>", "success": True, "error": ""},
 ]
 
 
 def test_file_encryption_telem_send(spy_send_telemetry):
     file_encryption_telem_1 = FileEncryptionTelem(
-        ENCRYPTION_ATTEMPTS[0]["path"], ENCRYPTION_ATTEMPTS[0]["error"]
+        ENCRYPTION_ATTEMPTS[0]["path"],
+        ENCRYPTION_ATTEMPTS[0]["success"],
+        ENCRYPTION_ATTEMPTS[0]["error"],
     )
     file_encryption_telem_2 = FileEncryptionTelem(
-        ENCRYPTION_ATTEMPTS[1]["path"], ENCRYPTION_ATTEMPTS[1]["error"]
+        ENCRYPTION_ATTEMPTS[1]["path"],
+        ENCRYPTION_ATTEMPTS[1]["success"],
+        ENCRYPTION_ATTEMPTS[1]["error"],
     )
 
     file_encryption_telem_1.add_telemetry_to_batch(file_encryption_telem_2)