diff --git a/monkey/monkey_island.py b/monkey/monkey_island.py
index f27efa01a..224b4788f 100644
--- a/monkey/monkey_island.py
+++ b/monkey/monkey_island.py
@@ -2,25 +2,43 @@ from gevent import monkey as gevent_monkey
 
 gevent_monkey.patch_all()
 
+import json  # noqa: E402
+
 from monkey_island.cc.main import main  # noqa: E402
-from monkey_island.cc.environment.environment_config import DEFAULT_SERVER_CONFIG_PATH  # noqa: E402
+from monkey_island.cc.consts import DEFAULT_SERVER_CONFIG_PATH, DEFAULT_LOGGING_CONFIG_PATH # noqa: E402
+from monkey_island.cc.island_logger import json_setup_logging  # noqa: E402
 
 
 def parse_cli_args():
     import argparse
+
     parser = argparse.ArgumentParser(description="Infection Monkey Island CnC Server.  See https://infectionmonkey.com",
                                      formatter_class=argparse.ArgumentDefaultsHelpFormatter)
     parser.add_argument("-s", "--setup-only", action="store_true",
                         help="Pass this flag to cause the Island to setup and exit without actually starting. "
                              "This is useful for preparing Island to boot faster later-on, so for "
                              "compiling/packaging Islands.")
-    parser.add_argument("-c", "--config", action="store",
+    parser.add_argument("--server-config", action="store",
                         help="The path to the server configuration file.",
                         default=DEFAULT_SERVER_CONFIG_PATH)
+    parser.add_argument("--logging-config", action="store",
+                        help="The path to the logging configuration file.",
+                        default=DEFAULT_LOGGING_CONFIG_PATH)
     args = parser.parse_args()
-    return (args.setup_only, args.config)
+
+    return (args.setup_only, args.server_config, args.logging_config)
 
 
 if "__main__" == __name__:
-    (is_setup_only, config) = parse_cli_args()
-    main(is_setup_only, config)
+    (is_setup_only, server_config, logging_config) = parse_cli_args()
+
+    # This is here in order to catch EVERYTHING, some functions are being called on
+    # imports, so the log init needs to be first.
+    try:
+        json_setup_logging(logging_config)
+    except(json.JSONDecodeError) as ex:
+        print(f"Error loading logging config: {ex}")
+        exit(1)
+
+    from monkey_island.cc.main import main
+    main(is_setup_only, server_config)
diff --git a/monkey/monkey_island/cc/main.py b/monkey/monkey_island/cc/main.py
index 3da752ec9..2018da89c 100644
--- a/monkey/monkey_island/cc/main.py
+++ b/monkey/monkey_island/cc/main.py
@@ -13,11 +13,7 @@ if str(MONKEY_ISLAND_DIR_BASE_PATH) not in sys.path:
     sys.path.insert(0, MONKEY_ISLAND_DIR_BASE_PATH)
 
 from monkey_island.cc.server_utils.consts import MONKEY_ISLAND_ABS_PATH  # noqa: E402
-from monkey_island.cc.server_utils.island_logger import json_setup_logging  # noqa: E402
 
-# This is here in order to catch EVERYTHING, some functions are being called on imports the log init needs to be on top.
-json_setup_logging(default_path=Path(MONKEY_ISLAND_ABS_PATH, 'cc', 'island_logger_default_config.json'),
-                   default_level=logging.DEBUG)
 logger = logging.getLogger(__name__)
 
 import monkey_island.cc.environment.environment_singleton as env_singleton  # noqa: E402
diff --git a/monkey/monkey_island/cc/server_utils/consts.py b/monkey/monkey_island/cc/server_utils/consts.py
index 44bcb5eba..4c793b587 100644
--- a/monkey/monkey_island/cc/server_utils/consts.py
+++ b/monkey/monkey_island/cc/server_utils/consts.py
@@ -12,3 +12,7 @@ DEFAULT_SERVER_CONFIG_PATH = os.path.join(
 DEFAULT_DEVELOP_SERVER_CONFIG_PATH = os.path.join(
     MONKEY_ISLAND_ABS_PATH, "cc", "server_config.json.develop"
 )
+
+DEFAULT_LOGGING_CONFIG_PATH = os.path.join(
+    MONKEY_ISLAND_ABS_PATH, "cc", "island_logger_default_config.json"
+)
diff --git a/monkey/monkey_island/cc/server_utils/island_logger.py b/monkey/monkey_island/cc/server_utils/island_logger.py
index 826ddca78..f8eca8cbb 100644
--- a/monkey/monkey_island/cc/server_utils/island_logger.py
+++ b/monkey/monkey_island/cc/server_utils/island_logger.py
@@ -2,11 +2,15 @@ import json
 import logging.config
 import os
 
+from monkey_island.cc.consts import DEFAULT_LOGGING_CONFIG_PATH
+
 __author__ = "Maor.Rayzin"
 
 
 def json_setup_logging(
-    default_path="logging.json", default_level=logging.INFO, env_key="LOG_CFG"
+    default_path=DEFAULT_LOGGING_CONFIG_PATH,
+    default_level=logging.INFO,
+    env_key="LOG_CFG",
 ):
     """
     Setup the logging configuration
@@ -15,7 +19,7 @@ def json_setup_logging(
     :param env_key: SYS ENV key to use for external configuration file path
     :return:
     """
-    path = default_path
+    path = os.path.expanduser(default_path)
     value = os.getenv(env_key, None)
 
     if value: