diff --git a/src/khoj/app/settings.py b/src/khoj/app/settings.py
index 721bcc87..97a058da 100644
--- a/src/khoj/app/settings.py
+++ b/src/khoj/app/settings.py
@@ -24,7 +24,7 @@ BASE_DIR = Path(__file__).resolve().parent.parent.parent.parent
 SECRET_KEY = os.getenv("KHOJ_DJANGO_SECRET_KEY")
 
 # SECURITY WARNING: don't run with debug turned on in production!
-DEBUG = os.getenv("KHOJ_DEBUG", "False") == "True"
+DEBUG = os.getenv("KHOJ_DEBUG") == "True"
 
 ALLOWED_HOSTS = [".khoj.dev", "localhost", "127.0.0.1", "[::1]", "beta.khoj.dev"]
 
diff --git a/src/khoj/main.py b/src/khoj/main.py
index c5e1f277..b832151c 100644
--- a/src/khoj/main.py
+++ b/src/khoj/main.py
@@ -3,6 +3,8 @@
 """
 
 # Standard Packages
+from contextlib import redirect_stdout
+import io
 import os
 import sys
 import locale
@@ -33,10 +35,14 @@ os.environ.setdefault("DJANGO_SETTINGS_MODULE", "khoj.app.settings")
 django.setup()
 
 # Initialize Django Database
-call_command("migrate", "--noinput")
+db_migrate_output = io.StringIO()
+with redirect_stdout(db_migrate_output):
+    call_command("migrate", "--noinput")
 
 # Initialize Django Static Files
-call_command("collectstatic", "--noinput")
+collectstatic_output = io.StringIO()
+with redirect_stdout(collectstatic_output):
+    call_command("collectstatic", "--noinput")
 
 # Initialize the Application Server
 app = FastAPI()
@@ -79,14 +85,16 @@ def run(should_start_server=True):
     args = cli(state.cli_args)
     set_state(args)
 
-    logger.info(f"🚒 Initializing Khoj v{state.khoj_version}")
-
     # Set Logging Level
     if args.verbose == 0:
         logger.setLevel(logging.INFO)
     elif args.verbose >= 1:
         logger.setLevel(logging.DEBUG)
 
+    logger.info(f"🚒 Initializing Khoj v{state.khoj_version}")
+    logger.info(f"📦 Initializing DB:\n{db_migrate_output.getvalue().strip()}")
+    logger.debug(f"🌍 Initializing Web Client:\n{collectstatic_output.getvalue().strip()}")
+
     initialization()
 
     # Create app directory, if it doesn't exist