diff --git a/index.js b/index.js
index ca977bbc1..b437b9c43 100644
--- a/index.js
+++ b/index.js
@@ -1,28 +1,56 @@
 // @flow
 require('./init');
 
-if (process.env.NODE_ENV === 'production') {
-  console.log(
-    '\n\x1b[33m%s\x1b[0m',
-    'Running Outline in production mode. Use `yarn dev` to run in development with live code reloading'
-  );
-} else if (process.env.NODE_ENV === 'development') {
-  console.log(
-    '\n\x1b[33m%s\x1b[0m',
-    'Running Outline in development mode with hot reloading. To run Outline in production mode, use `yarn start`'
-  );
-}
-
 if (
   !process.env.SECRET_KEY ||
-  process.env.SECRET_KEY ===
-    'F0E5AD933D7F6FD8F4DBB3E038C501C052DC0593C686D21ACB30AE205D2F634B'
+  process.env.SECRET_KEY === 'generate_a_new_key'
 ) {
   console.error(
-    'Please set SECRET_KEY env variable with output of `openssl rand -hex 32`'
+    'The SECRET_KEY env variable must be set with the output of `openssl rand -hex 32`'
   );
   // $FlowFixMe
   process.exit(1);
 }
 
+if (process.env.AWS_ACCESS_KEY_ID && !process.env.AWS_REGION) {
+  console.error(
+    'The AWS_REGION env variable must be set when using AWS, e.g (us-east-1)'
+  );
+  // $FlowFixMe
+  process.exit(1);
+}
+
+if (!process.env.URL) {
+  console.error(
+    'The URL env variable must be set to the externally accessible URL, e.g (https://www.getoutline.com)'
+  );
+  // $FlowFixMe
+  process.exit(1);
+}
+
+if (!process.env.DATABASE_URL) {
+  console.error(
+    'The DATABASE_URL env variable must be set to the location of your postgres server, including authentication and port'
+  );
+  // $FlowFixMe
+  process.exit(1);
+}
+
+if (!process.env.REDIS_URL) {
+  console.error(
+    'The REDIS_URL env variable must be set to the location of your redis server, including authentication and port'
+  );
+  // $FlowFixMe
+  process.exit(1);
+}
+
+if (process.env.NODE_ENV === 'production') {
+  console.log('\n\x1b[33m%s\x1b[0m', 'Running Outline in production mode.');
+} else if (process.env.NODE_ENV === 'development') {
+  console.log(
+    '\n\x1b[33m%s\x1b[0m',
+    'Running Outline in development mode with hot reloading. To run Outline in production mode set the NODE_ENV env variable to "production"'
+  );
+}
+
 require('./server');