diff --git a/monkey/common/utils/exceptions.py b/monkey/common/utils/exceptions.py
index 8396b423b..632c08991 100644
--- a/monkey/common/utils/exceptions.py
+++ b/monkey/common/utils/exceptions.py
@@ -52,3 +52,7 @@ class FindingWithoutDetailsError(Exception):
 
 class DomainControllerNameFetchError(FailedExploitationError):
     """ Raise on failed attempt to extract domain controller's name """
+
+
+class InsecurePermissionsError(Exception):
+    """ Raise when a file does not have permissions that are secure enough """
diff --git a/monkey/monkey_island/cc/server_setup.py b/monkey/monkey_island/cc/server_setup.py
index 4eaa13131..faec1ec96 100644
--- a/monkey/monkey_island/cc/server_setup.py
+++ b/monkey/monkey_island/cc/server_setup.py
@@ -22,13 +22,13 @@ from monkey_island.cc.arg_parser import IslandCmdArgs  # noqa: E402
 from monkey_island.cc.arg_parser import parse_cli_args  # noqa: E402
 from monkey_island.cc.resources.monkey_download import MonkeyDownload  # noqa: E402
 from monkey_island.cc.server_utils.bootloader_server import BootloaderHttpServer  # noqa: E402
-from monkey_island.cc.server_utils.consts import MONKEY_ISLAND_ABS_PATH  # noqa: E402
 from monkey_island.cc.server_utils.encryptor import initialize_encryptor  # noqa: E402
 from monkey_island.cc.server_utils.island_logger import reset_logger, setup_logging  # noqa: E402
 from monkey_island.cc.services.initialize import initialize_services  # noqa: E402
 from monkey_island.cc.services.reporting.exporter_init import populate_exporter_list  # noqa: E402
 from monkey_island.cc.services.utils.network_utils import local_ip_addresses  # noqa: E402
 from monkey_island.cc.setup.island_config_options import IslandConfigOptions  # noqa: E402
+from monkey_island.cc.setup.certificate.certificate_setup import setup_certificate  # noqa: E402
 from monkey_island.cc.setup.mongo.database_initializer import init_collections  # noqa: E402
 from monkey_island.cc.setup.mongo.mongo_setup import (  # noqa: E402
     MONGO_URL,
@@ -83,8 +83,7 @@ def _start_island_server(should_setup_only, config_options: IslandConfigOptions)
     populate_exporter_list()
     app = init_app(MONGO_URL)
 
-    crt_path = str(Path(MONKEY_ISLAND_ABS_PATH, "cc", "server.crt"))
-    key_path = str(Path(MONKEY_ISLAND_ABS_PATH, "cc", "server.key"))
+    crt_path, key_path = setup_certificate(config_options)
 
     init_collections()
 
diff --git a/monkey/monkey_island/cc/server_utils/consts.py b/monkey/monkey_island/cc/server_utils/consts.py
index a14c69d0b..2a50e01aa 100644
--- a/monkey/monkey_island/cc/server_utils/consts.py
+++ b/monkey/monkey_island/cc/server_utils/consts.py
@@ -46,3 +46,6 @@ DEFAULT_DEVELOP_SERVER_CONFIG_PATH = os.path.join(
 
 DEFAULT_LOG_LEVEL = "INFO"
 DEFAULT_START_MONGO_DB = True
+
+DEFAULT_CRT_PATH = str(Path(MONKEY_ISLAND_ABS_PATH, "cc", "server.crt"))
+DEFAULT_KEY_PATH = str(Path(MONKEY_ISLAND_ABS_PATH, "cc", "server.key"))
diff --git a/monkey/monkey_island/cc/setup/certificate/certificate_setup.py b/monkey/monkey_island/cc/setup/certificate/certificate_setup.py
new file mode 100644
index 000000000..959025e03
--- /dev/null
+++ b/monkey/monkey_island/cc/setup/certificate/certificate_setup.py
@@ -0,0 +1,23 @@
+import os
+
+from common.utils.exceptions import InsecurePermissionsError
+from monkey_island.setup.island_config_options import IslandConfigOptions
+
+
+def setup_certificate(config_options: IslandConfigOptions) -> (str, str):
+    crt_path = config_options.crt_path
+    key_path = config_options.key_path
+
+    # check paths
+    for file in [crt_path, key_path]:
+        if not os.path.exists(file):
+            raise FileNotFoundError(f"File not found at {file}. Exiting.")
+
+        if not has_sufficient_permissions(file):
+            raise InsecurePermissionsError(f"{file} has insecure permissions. Exiting.")
+
+    return crt_path, key_path
+
+
+def has_sufficient_permissions():
+    pass
diff --git a/monkey/monkey_island/cc/setup/island_config_options.py b/monkey/monkey_island/cc/setup/island_config_options.py
index 5ce62ba2e..0df903587 100644
--- a/monkey/monkey_island/cc/setup/island_config_options.py
+++ b/monkey/monkey_island/cc/setup/island_config_options.py
@@ -3,7 +3,9 @@ from __future__ import annotations
 import os
 
 from monkey_island.cc.server_utils.consts import (
+    DEFAULT_CRT_PATH,
     DEFAULT_DATA_DIR,
+    DEFAULT_KEY_PATH,
     DEFAULT_LOG_LEVEL,
     DEFAULT_START_MONGO_DB,
 )
@@ -14,8 +16,12 @@ class IslandConfigOptions:
         self.data_dir = os.path.expandvars(
             os.path.expanduser(config_contents.get("data_dir", DEFAULT_DATA_DIR))
         )
+
         self.log_level = config_contents.get("log_level", DEFAULT_LOG_LEVEL)
 
         self.start_mongodb = config_contents.get(
             "mongodb", {"start_mongodb": DEFAULT_START_MONGO_DB}
         ).get("start_mongodb", DEFAULT_START_MONGO_DB)
+
+        self.crt_path = config_contents.get("cert_path", DEFAULT_CRT_PATH)
+        self.key_path = config_contents.get("cert_path", DEFAULT_KEY_PATH)