diff --git a/monkey/monkey_island/cc/server_utils/consts.py b/monkey/monkey_island/cc/server_utils/consts.py
index ab9261140..f5cff557c 100644
--- a/monkey/monkey_island/cc/server_utils/consts.py
+++ b/monkey/monkey_island/cc/server_utils/consts.py
@@ -36,7 +36,8 @@ MONGO_EXECUTABLE_PATH = (
 )
 MONGO_CONNECTION_TIMEOUT = 15
 
-DEFAULT_SERVER_CONFIG_PATH = str(Path(MONKEY_ISLAND_ABS_PATH, "cc", SERVER_CONFIG_FILENAME))
+PACKAGE_CONFIG_PATH = Path(MONKEY_ISLAND_ABS_PATH, "cc", SERVER_CONFIG_FILENAME)
+USER_CONFIG_PATH = Path(os.getcwd(), SERVER_CONFIG_FILENAME)
 
 DEFAULT_LOG_LEVEL = "INFO"
 
diff --git a/monkey/monkey_island/cc/setup/config_setup.py b/monkey/monkey_island/cc/setup/config_setup.py
index b997e35d4..77652ddba 100644
--- a/monkey/monkey_island/cc/setup/config_setup.py
+++ b/monkey/monkey_island/cc/setup/config_setup.py
@@ -4,7 +4,7 @@ from pathlib import Path
 
 from common.utils.file_utils import expand_path
 from monkey_island.cc.arg_parser import IslandCmdArgs
-from monkey_island.cc.server_utils.consts import DEFAULT_SERVER_CONFIG_PATH
+from monkey_island.cc.server_utils.consts import PACKAGE_CONFIG_PATH, USER_CONFIG_PATH
 from monkey_island.cc.setup.island_config_options import IslandConfigOptions
 
 logger = getLogger(__name__)
@@ -13,7 +13,9 @@ logger = getLogger(__name__)
 def get_server_config(island_args: IslandCmdArgs) -> IslandConfigOptions:
     config = IslandConfigOptions({})
 
-    update_config_from_file(config, DEFAULT_SERVER_CONFIG_PATH)
+    update_config_from_file(config, PACKAGE_CONFIG_PATH)
+
+    update_config_from_file(config, USER_CONFIG_PATH)
 
     if island_args.server_config_path:
         path_to_config = expand_path(island_args.server_config_path)
@@ -26,6 +28,7 @@ def update_config_from_file(config: IslandConfigOptions, config_path: Path):
     try:
         config_from_file = load_server_config_from_file(config_path)
         config.update(config_from_file)
+        logger.info(f"Server config updated from {config_path}")
     except OSError:
         logger.info(f"Server config not found in path {config_path}")
 
diff --git a/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_consts.py b/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_consts.py
index 26d7bc583..996226e0d 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_consts.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/server_utils/test_consts.py
@@ -15,4 +15,4 @@ def test_default_server_config_file_path():
     else:
         server_file_path = f"{consts.MONKEY_ISLAND_ABS_PATH}/cc/{consts.SERVER_CONFIG_FILENAME}"
 
-    assert consts.DEFAULT_SERVER_CONFIG_PATH == server_file_path
+    assert consts.PACKAGE_CONFIG_PATH == server_file_path
diff --git a/monkey/tests/unit_tests/monkey_island/cc/setup/test_server_setup.py b/monkey/tests/unit_tests/monkey_island/cc/setup/test_server_setup.py
index cb3511b10..c3a6ee636 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/setup/test_server_setup.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/setup/test_server_setup.py
@@ -12,15 +12,23 @@ BAD_JSON = '{"data_dir": "C:\\test\\test"'
 
 
 @pytest.fixture
-def user_server_config_path(tmpdir) -> Path:
+def cmd_server_config_path(tmpdir) -> Path:
+    # Represents the config that user can provide via cmd arguments
     return tmpdir / "fake_server_config.json"
 
 
 @pytest.fixture
-def deployment_server_config_path(tmpdir) -> Path:
+def user_default_server_config_path(tmpdir) -> Path:
+    # Represents the config that can be put into the install dir
     return tmpdir / "fake_server_config2.json"
 
 
+@pytest.fixture
+def deployment_server_config_path(tmpdir) -> Path:
+    # Represents the config that is built in, deployment specific
+    return tmpdir / "fake_server_config3.json"
+
+
 def create_server_config(config_contents: str, server_config_path: Path):
     with open(server_config_path, "w") as file:
         file.write(config_contents)
@@ -34,6 +42,14 @@ def mock_deployment_config_path(monkeypatch, deployment_server_config_path):
     )
 
 
+@pytest.fixture(autouse=True)
+def mock_user_config_path(monkeypatch, deployment_server_config_path):
+    monkeypatch.setattr(
+        "monkey_island.cc.setup.config_setup.USER_CONFIG_PATH",
+        deployment_server_config_path,
+    )
+
+
 def test_extract_config_defaults():
     expected = IslandConfigOptions({})
     assert (
@@ -42,7 +58,7 @@ def test_extract_config_defaults():
     )
 
 
-def test_package_config_overrides_defaults(deployment_server_config_path):
+def test_deployment_config_overrides_defaults(deployment_server_config_path):
     expected = IslandConfigOptions({"key_path": "/key_path_2"})
     create_server_config(dumps({"key_path": "/key_path_2"}), deployment_server_config_path)
     assert (
@@ -51,19 +67,32 @@ def test_package_config_overrides_defaults(deployment_server_config_path):
     )
 
 
-def test_user_config_overrides_package_config(
-    deployment_server_config_path, user_server_config_path
+def test_user_config_overrides_deployment(
+    deployment_server_config_path, cmd_server_config_path, user_default_server_config_path
 ):
     expected = IslandConfigOptions({"key_path": "/key_path_3"})
     create_server_config(dumps({"key_path": "/key_path_2"}), deployment_server_config_path)
-    create_server_config(dumps({"key_path": "/key_path_3"}), user_server_config_path)
+    create_server_config(dumps({"key_path": "/key_path_3"}), user_default_server_config_path)
     extracted_config = _extract_config(
-        IslandCmdArgs(setup_only=False, server_config_path=user_server_config_path)
+        IslandCmdArgs(setup_only=False, server_config_path=cmd_server_config_path)
     )
     assert expected.__dict__ == extracted_config.__dict__
 
 
-def test_malformed_json(user_server_config_path):
-    create_server_config(BAD_JSON, user_server_config_path)
+def test_cmd_config_overrides_everything(
+    deployment_server_config_path, cmd_server_config_path, user_default_server_config_path
+):
+    expected = IslandConfigOptions({"key_path": "/key_path_4"})
+    create_server_config(dumps({"key_path": "/key_path_2"}), deployment_server_config_path)
+    create_server_config(dumps({"key_path": "/key_path_3"}), user_default_server_config_path)
+    create_server_config(dumps({"key_path": "/key_path_4"}), cmd_server_config_path)
+    extracted_config = _extract_config(
+        IslandCmdArgs(setup_only=False, server_config_path=cmd_server_config_path)
+    )
+    assert expected.__dict__ == extracted_config.__dict__
+
+
+def test_malformed_json(cmd_server_config_path):
+    create_server_config(BAD_JSON, cmd_server_config_path)
     with pytest.raises(SystemExit):
-        _extract_config(IslandCmdArgs(setup_only=False, server_config_path=user_server_config_path))
+        _extract_config(IslandCmdArgs(setup_only=False, server_config_path=cmd_server_config_path))