diff --git a/webapp/README.md b/webapp/README.md
index 2fcf561..a3a8206 100644
--- a/webapp/README.md
+++ b/webapp/README.md
@@ -20,15 +20,22 @@ This service ports the Discord AdventureBot experience to a standalone web stack
    ```bash
    npm install
    ```
-3. Run the development server with automatic reloads:
+3. Create or refresh the database schema and seed data from the repository dump:
+   ```bash
+   npm run db:setup
+   ```
+   This script creates the configured database if it does not exist, then installs the AdventureBot tables and seed rows from
+   `database/dump.sql`.
+
+4. Run the development server with automatic reloads:
    ```bash
    npm run dev
    ```
-4. Build the production bundle:
+5. Build the production bundle:
    ```bash
    npm run build
    ```
-5. Start the compiled server:
+6. Start the compiled server:
    ```bash
    npm start
    ```
diff --git a/webapp/package.json b/webapp/package.json
index 627f5cf..b531f37 100644
--- a/webapp/package.json
+++ b/webapp/package.json
@@ -9,7 +9,8 @@
     "dev": "ts-node-dev --respawn --transpile-only src/server.ts",
     "build": "tsc --project tsconfig.json",
     "start": "node dist/server.js",
-    "lint": "eslint \"src/**/*.ts\""
+    "lint": "eslint \"src/**/*.ts\"",
+    "db:setup": "npm run build && node dist/db/setup.js"
   },
   "engines": {
     "node": ">=18"
@@ -37,4 +38,4 @@
     "ts-node-dev": "^2.0.0",
     "typescript": "5.5.4"
   }
-}
+}
\ No newline at end of file
diff --git a/webapp/src/db/setup.ts b/webapp/src/db/setup.ts
new file mode 100644
index 0000000..78308b6
--- /dev/null
+++ b/webapp/src/db/setup.ts
@@ -0,0 +1,85 @@
+import fs from 'fs';
+import path from 'path';
+import mysql, { RowDataPacket } from 'mysql2/promise';
+import { getEnv } from '../config/env.js';
+import { logger } from '../logger.js';
+
+const env = getEnv();
+
+const loadSetupStatements = (): string[] => {
+  const sqlPath = path.resolve(process.cwd(), '..', 'database', 'dump.sql');
+  const sql = fs.readFileSync(sqlPath, 'utf8');
+
+  const cleaned = sql
+    .split('\n')
+    .map((line) => line.trim())
+    .filter((line) => line && !line.startsWith('--'))
+    .join('\n');
+
+  return cleaned
+    .split(';')
+    .map((statement) => statement.trim())
+    .filter((statement) => statement.length > 0);
+};
+
+const databaseExists = async (connection: mysql.Connection): Promise<boolean> => {
+  const [rows] = await connection.query<RowDataPacket[]>(
+    'SELECT SCHEMA_NAME FROM INFORMATION_SCHEMA.SCHEMATA WHERE SCHEMA_NAME = ?',
+    [env.mysql.database]
+  );
+
+  return rows.length > 0;
+};
+
+const hasSchema = async (connection: mysql.Connection): Promise<boolean> => {
+  const [rows] = await connection.query<RowDataPacket[]>("SHOW TABLES LIKE 'difficulties'");
+  return rows.length > 0;
+};
+
+export const ensureDatabaseSetup = async (): Promise<void> => {
+  const adminConnection = await mysql.createConnection({
+    host: env.mysql.host,
+    port: env.mysql.port,
+    user: env.mysql.user,
+    password: env.mysql.password,
+  });
+
+  try {
+    const exists = await databaseExists(adminConnection);
+    if (!exists) {
+      await adminConnection.query(`CREATE DATABASE IF NOT EXISTS \`${env.mysql.database}\``);
+      logger.info({ database: env.mysql.database }, 'Created missing database');
+    }
+  } finally {
+    await adminConnection.end();
+  }
+
+  const connection = await mysql.createConnection({
+    host: env.mysql.host,
+    port: env.mysql.port,
+    user: env.mysql.user,
+    password: env.mysql.password,
+    database: env.mysql.database,
+    multipleStatements: false,
+  });
+
+  try {
+    const schemaPresent = await hasSchema(connection);
+    if (schemaPresent) {
+      logger.info('Database schema already present; skipping setup');
+      return;
+    }
+
+    const statements = loadSetupStatements();
+    for (const statement of statements) {
+      await connection.query(statement);
+    }
+
+    logger.info('Database schema and seed data installed');
+  } catch (error) {
+    logger.error({ err: error }, 'Database setup failed');
+    throw error;
+  } finally {
+    await connection.end();
+  }
+};
diff --git a/webapp/src/server.ts b/webapp/src/server.ts
index 07622a5..b615484 100644
--- a/webapp/src/server.ts
+++ b/webapp/src/server.ts
@@ -1,10 +1,21 @@
 import { createApp } from './app.js';
 import { getEnv } from './config/env.js';
+import { ensureDatabaseSetup } from './db/setup.js';
 import { logger } from './logger.js';
 
 const env = getEnv();
 const app = createApp();
 
-app.listen(env.port, () => {
-  logger.info({ port: env.port, nodeEnv: env.nodeEnv }, 'Web app server listening');
-});
+const startServer = async () => {
+  try {
+    await ensureDatabaseSetup();
+    app.listen(env.port, () => {
+      logger.info({ port: env.port, nodeEnv: env.nodeEnv }, 'Web app server listening');
+    });
+  } catch (error) {
+    logger.error({ err: error }, 'Failed to start server');
+    process.exit(1);
+  }
+};
+
+startServer();
diff --git a/webapp/src/services/difficulties.ts b/webapp/src/services/difficulties.ts
index e4e8d1d..fc67691 100644
--- a/webapp/src/services/difficulties.ts
+++ b/webapp/src/services/difficulties.ts
@@ -1,6 +1,6 @@
-import { Difficulty, DifficultyDefinition } from './types.js';
+import { Difficulty, DifficultyDefinition, difficultyKeys } from './types.js';
 
-export const difficultyOrder: Difficulty[] = ['easy', 'medium', 'hard', 'crazy_catto'];
+export const difficultyOrder: Difficulty[] = [...difficultyKeys];
 
 export const difficultyDefinitions: Record<Difficulty, DifficultyDefinition> = {
   easy: {
@@ -63,4 +63,4 @@ export const difficultyDefinitions: Record<Difficulty, DifficultyDefinition> = {
 
 export const getDifficultyDefinition = (key: Difficulty): DifficultyDefinition => difficultyDefinitions[key];
 
-export const difficultyKeys = Object.keys(difficultyDefinitions) as Difficulty[];
+export { difficultyKeys };
diff --git a/webapp/src/services/types.ts b/webapp/src/services/types.ts
index db3f5ba..07cc666 100644
--- a/webapp/src/services/types.ts
+++ b/webapp/src/services/types.ts
@@ -1,4 +1,5 @@
-export type Difficulty = 'easy' | 'medium' | 'hard' | 'crazy_catto';
+export const difficultyKeys = ['easy', 'medium', 'hard', 'crazy_catto'] as const;
+export type Difficulty = (typeof difficultyKeys)[number];
 
 export interface DifficultyDefinition {
   key: Difficulty;