diff --git a/monkey/monkey_island/cc/server_utils/consts.py b/monkey/monkey_island/cc/server_utils/consts.py
index 2a50e01aa..333008c6d 100644
--- a/monkey/monkey_island/cc/server_utils/consts.py
+++ b/monkey/monkey_island/cc/server_utils/consts.py
@@ -45,6 +45,7 @@ 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"))
diff --git a/monkey/monkey_island/cc/setup/island_config_options.py b/monkey/monkey_island/cc/setup/island_config_options.py
index 0df903587..e8a0f7016 100644
--- a/monkey/monkey_island/cc/setup/island_config_options.py
+++ b/monkey/monkey_island/cc/setup/island_config_options.py
@@ -23,5 +23,9 @@ class IslandConfigOptions:
             "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)
+        self.crt_path = os.path.expandvars(
+            os.path.expanduser(config_contents.get("cert_path", DEFAULT_CRT_PATH))
+        )
+        self.key_path = os.path.expandvars(
+            os.path.expanduser(config_contents.get("key_path", DEFAULT_KEY_PATH))
+        )