diff --git a/monkey/infection_monkey/network/scan_target_generator.py b/monkey/infection_monkey/network/scan_target_generator.py
index 734cc90c6..6cec82223 100644
--- a/monkey/infection_monkey/network/scan_target_generator.py
+++ b/monkey/infection_monkey/network/scan_target_generator.py
@@ -1,5 +1,6 @@
 import itertools
 import logging
+import socket
 from collections import namedtuple
 from typing import List
 
@@ -32,7 +33,7 @@ def compile_scan_target_list(
     scan_targets = _remove_interface_ips(scan_targets, local_network_interfaces)
     scan_targets = _remove_blocklisted_ips(scan_targets, blocklisted_ips)
     scan_targets = _remove_redundant_targets(scan_targets)
-    scan_targets.sort()
+    scan_targets.sort(key=lambda network_address: socket.inet_aton(network_address.ip))
 
     return scan_targets
 
diff --git a/monkey/tests/unit_tests/infection_monkey/network/test_scan_target_generator.py b/monkey/tests/unit_tests/infection_monkey/network/test_scan_target_generator.py
index 4f3e49b64..03febe44c 100644
--- a/monkey/tests/unit_tests/infection_monkey/network/test_scan_target_generator.py
+++ b/monkey/tests/unit_tests/infection_monkey/network/test_scan_target_generator.py
@@ -466,3 +466,18 @@ def test_invalid_blocklisted_ip():
             blocklisted_ips=blocklisted,
             enable_local_network_scan=False,
         )
+
+
+def test_sorted_scan_targets():
+    expected_results = [f"10.1.0.{i}" for i in range(0, 255)]
+    expected_results.extend([f"10.2.0.{i}" for i in range(0, 255)])
+    expected_results.extend([f"10.10.0.{i}" for i in range(0, 255)])
+    expected_results.extend([f"10.20.0.{i}" for i in range(0, 255)])
+
+    scan_targets = compile_scan_target_list(
+        [], ["10.1.0.0/24", "10.10.0.0/24", "10.20.0.0/24", "10.2.0.0/24"], [], [], False
+    )
+
+    actual_results = [network_address.ip for network_address in scan_targets]
+
+    assert expected_results == actual_results