diff --git a/groove/cli.py b/groove/cli.py
index 237e97f..6473e54 100644
--- a/groove/cli.py
+++ b/groove/cli.py
@@ -3,26 +3,19 @@ import os
 import typer
 
 from dotenv import load_dotenv
-from sqlalchemy import create_engine
-from sqlalchemy.orm import sessionmaker
 
-from groove import ondemand
-from groove.db import metadata
+from groove import webserver
+from groove.db.manager import database_manager
 
 
 app = typer.Typer()
 
 
-@app.command()
 def initialize():
     load_dotenv()
-
-    # todo: abstract this and replace in_memory_db fixture
-    engine = create_engine(f"sqlite:///{os.environ.get('DATABASE_PATH')}", future=True)
-    Session = sessionmaker(bind=engine, future=True)
-    session = Session()
-    metadata.create_all(bind=engine)
-    session.close()
+    debug = os.getenv('DEBUG', None)
+    logging.basicConfig(format='%(asctime)s - %(message)s',
+                        level=logging.DEBUG if debug else logging.INFO)
 
 
 @app.command()
@@ -43,21 +36,11 @@ def server(
     """
     Start the Groove on Demand playlsit server.
     """
-    load_dotenv()
-
-    ondemand.initialize()
-
     print("Starting Groove On Demand...")
-
-    debug = os.getenv('DEBUG', None)
-    logging.basicConfig(format='%(asctime)s - %(message)s', level=logging.DEBUG if debug else logging.INFO)
-    ondemand.server.run(
-        host=os.getenv('HOST', host),
-        port=os.getenv('PORT', port),
-        debug=debug,
-        server='paste',
-        quiet=True
-    )
+    initialize()
+    with database_manager as manager:
+        manager.import_from_filesystem()
+    webserver.start(host=host, port=port, debug=debug)
 
 
 if __name__ == '__main__':
diff --git a/groove/db/__init__.py b/groove/db/__init__.py
new file mode 100644
index 0000000..bccd04d
--- /dev/null
+++ b/groove/db/__init__.py
@@ -0,0 +1 @@
+from groove.db.schema import metadata, track, playlist, entry
diff --git a/groove/db/manager.py b/groove/db/manager.py
new file mode 100644
index 0000000..92a14a1
--- /dev/null
+++ b/groove/db/manager.py
@@ -0,0 +1,43 @@
+import os
+
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+
+from . import metadata
+
+
+class DatabaseManager:
+    """
+    A context manager for working with sqllite database.
+    """
+
+    def __init__(self):
+        self._engine = None
+        self._session = None
+
+    @property
+    def engine(self):
+        if not self._engine:
+            self._engine = create_engine(f"sqlite:///{os.environ.get('DATABASE_PATH')}", future=True)
+        return self._engine
+
+    @property
+    def session(self):
+        if not self._session:
+            Session = sessionmaker(bind=self.engine, future=True)
+            self._session = Session()
+        return self._session
+
+    def import_from_filesystem(self):
+        pass
+
+    def __enter__(self):
+        metadata.create_all(bind=self.engine)
+        return self
+
+    def __exit__(self, exc_type, exc_value, traceback):
+        if self.session:
+            self.session.close()
+
+
+database_manager = DatabaseManager()
diff --git a/groove/db.py b/groove/db/schema.py
similarity index 100%
rename from groove/db.py
rename to groove/db/schema.py
diff --git a/groove/ondemand.py b/groove/webserver.py
similarity index 67%
rename from groove/ondemand.py
rename to groove/webserver.py
index 2b8a909..d1dd6c9 100644
--- a/groove/ondemand.py
+++ b/groove/webserver.py
@@ -11,11 +11,20 @@ from groove.helper import PlaylistDatabaseHelper
 server = bottle.Bottle()
 
 
-def initialize():
+def start(host: str, port: int, debug: bool) -> None:
     """
-    Configure the sqlite database.
+    Start the Bottle app.
     """
+    logging.debug(f"Configuring sqllite using {os.environ.get('DATABASE_PATH')}")
     server.install(sqlite.Plugin(dbfile=os.environ.get('DATABASE_PATH')))
+    logging.debug(f"Configuring webserver with host={host}, port={port}, debug={debug}")
+    server.run(
+        host=os.getenv('HOST', host),
+        port=os.getenv('PORT', port),
+        debug=debug,
+        server='paste',
+        quiet=True
+    )
 
 
 @server.route('/')
diff --git a/test/test_ondemand.py b/test/test_webserver.py
similarity index 75%
rename from test/test_ondemand.py
rename to test/test_webserver.py
index 2a5c62a..e026cf5 100644
--- a/test/test_ondemand.py
+++ b/test/test_webserver.py
@@ -7,23 +7,18 @@ import atheris
 import bottle
 from boddle import boddle
 
-from groove import ondemand
-
-
-@pytest.fixture(autouse=True, scope='session')
-def init_db():
-    ondemand.initialize()
+from groove import webserver
 
 
 def test_server():
     with boddle():
-        ondemand.index()
+        webserver.index()
         assert bottle.response.status_code == 200
 
 
 def test_auth_with_valid_credentials():
     with boddle(auth=(os.environ.get('USERNAME'), os.environ.get('PASSWORD'))):
-        ondemand.build()
+        webserver.build()
         assert bottle.response.status_code == 200
 
 
@@ -31,7 +26,7 @@ def test_auth_random_input():
 
     def auth(fuzzed_input):
         with boddle(auth=(fuzzed_input, fuzzed_input)):
-            response = ondemand.build()
+            response = webserver.build()
             assert response.status_code == 401
 
     atheris.Setup([sys.argv[0], "-atheris_runs=100000"], auth)
@@ -49,11 +44,11 @@ def test_auth_random_input():
 ])
 def test_playlist(db, slug, expected):
     with boddle():
-        response = ondemand.get_playlist(slug, db)
+        response = webserver.get_playlist(slug, db)
         assert response.status_code == expected
 
 
 def test_playlist_on_empty_db(in_memory_db):
     with boddle():
-        response = ondemand.get_playlist('some-slug', in_memory_db)
+        response = webserver.get_playlist('some-slug', in_memory_db)
         assert response.status_code == 404