diff --git a/Dockerfile b/Dockerfile
index fe236f9..8c776f3 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -31,9 +31,12 @@ COPY . .
 RUN mkdir -p /app/config /app/database /app/logs /app/downloads /app/Transfer && \
     chown -R soulsync:soulsync /app
 
-# Copy example config as default config.json and set proper ownership
-RUN cp /app/config/config.example.json /app/config/config.json && \
-    chown soulsync:soulsync /app/config/config.json
+# Create defaults directory and copy template files
+# These will be used by entrypoint.sh to initialize empty volumes
+RUN mkdir -p /defaults && \
+    cp /app/config/config.example.json /defaults/config.json && \
+    cp /app/config/settings.py /defaults/settings.py && \
+    chmod 644 /defaults/config.json /defaults/settings.py
 
 # Create volume mount points
 VOLUME ["/app/config", "/app/database", "/app/logs", "/app/downloads", "/app/Transfer"]
diff --git a/entrypoint.sh b/entrypoint.sh
index fe8faf2..904bcfc 100644
--- a/entrypoint.sh
+++ b/entrypoint.sh
@@ -46,6 +46,31 @@ fi
 echo "🎭 Setting UMASK to $UMASK"
 umask "$UMASK"
 
+# Initialize config files if they don't exist (first-time setup)
+echo "🔍 Checking for configuration files..."
+
+if [ ! -f "/app/config/config.json" ]; then
+    echo "   📄 Creating default config.json..."
+    cp /defaults/config.json /app/config/config.json
+    chown soulsync:soulsync /app/config/config.json
+else
+    echo "   ✅ config.json already exists"
+fi
+
+if [ ! -f "/app/config/settings.py" ]; then
+    echo "   📄 Creating default settings.py..."
+    cp /defaults/settings.py /app/config/settings.py
+    chown soulsync:soulsync /app/config/settings.py
+else
+    echo "   ✅ settings.py already exists"
+fi
+
+# Ensure all directories exist and have proper permissions
+mkdir -p /app/config /app/database /app/logs /app/downloads /app/Transfer
+chown -R soulsync:soulsync /app/config /app/database /app/logs /app/downloads /app/Transfer
+
+echo "✅ Configuration initialized successfully"
+
 # Display final user info
 echo "👤 Running as:"
 echo "   User: $(id -u soulsync):$(id -g soulsync) ($(id -un soulsync):$(id -gn soulsync))"