diff --git a/monkey/monkey_island/cc/resources/pba_file_upload.py b/monkey/monkey_island/cc/resources/pba_file_upload.py
index 6ae209a12..01cae595e 100644
--- a/monkey/monkey_island/cc/resources/pba_file_upload.py
+++ b/monkey/monkey_island/cc/resources/pba_file_upload.py
@@ -28,10 +28,6 @@ class FileUpload(flask_restful.Resource):
     File upload endpoint used to exchange files with filepond component on the front-end
     """
 
-    def __init__(self):
-        # Create all directories on the way if they don't exist
-        Path(env_singleton.env.get_config().data_dir_abs_path).mkdir(parents=True, exist_ok=True)
-
     @jwt_required
     def get(self, file_type):
         """
diff --git a/monkey/monkey_island/cc/services/config.py b/monkey/monkey_island/cc/services/config.py
index 4b41501b4..3dbdd9039 100644
--- a/monkey/monkey_island/cc/services/config.py
+++ b/monkey/monkey_island/cc/services/config.py
@@ -9,6 +9,8 @@ import monkey_island.cc.environment.environment_singleton as env_singleton
 from monkey_island.cc.database import mongo
 from monkey_island.cc.server_utils.encryptor import get_encryptor
 from monkey_island.cc.services.config_schema.config_schema import SCHEMA
+
+# TODO: Remove circular dependency between ConfigService and PostBreachFilesService.
 from monkey_island.cc.services.post_breach_files import PostBreachFilesService
 from monkey_island.cc.services.utils.network_utils import local_ip_addresses
 
diff --git a/monkey/monkey_island/cc/services/initialize.py b/monkey/monkey_island/cc/services/initialize.py
index 45301946f..564babcac 100644
--- a/monkey/monkey_island/cc/services/initialize.py
+++ b/monkey/monkey_island/cc/services/initialize.py
@@ -6,4 +6,4 @@ def initialize_services(data_dir):
 
 
 def initialize_post_breach_file_service(data_dir):
-    PostBreachFilesService.DATA_DIR = data_dir
+    PostBreachFilesService.initialize(data_dir)
diff --git a/monkey/monkey_island/cc/services/post_breach_files.py b/monkey/monkey_island/cc/services/post_breach_files.py
index d0c1b6a56..a56c585de 100644
--- a/monkey/monkey_island/cc/services/post_breach_files.py
+++ b/monkey/monkey_island/cc/services/post_breach_files.py
@@ -1,6 +1,8 @@
 import logging
 import os
+from pathlib import Path
 
+# TODO: Remove circular dependency between ConfigService and PostBreachFilesService.
 import monkey_island.cc.services.config
 
 __author__ = "VakarisZ"
@@ -16,6 +18,14 @@ class PostBreachFilesService:
     DATA_DIR = None
     CUSTOM_PBA_DIRNAME = "custom_pbas"
 
+    # TODO: A number of these services should be instance objects instead of
+    # static/singleton hybrids. At the moment, this requires invasive refactoring that's
+    # not a priority.
+    @classmethod
+    def initialize(cls, data_dir):
+        cls.DATA_DIR = data_dir
+        Path(cls.get_custom_pba_directory()).mkdir(mode=0o0700, parents=True, exist_ok=True)
+
     @staticmethod
     def remove_PBA_files():
         if monkey_island.cc.services.config.ConfigService.get_config():