diff --git a/src/Roots/Acorn/Bootloader.php b/src/Roots/Acorn/Bootloader.php
index 15fa12b2..bd23b9de 100644
--- a/src/Roots/Acorn/Bootloader.php
+++ b/src/Roots/Acorn/Bootloader.php
@@ -266,6 +266,8 @@ public function getApplication(): ApplicationContract
     {
         $this->app ??= new Application($this->basePath(), $this->usePaths());
 
+        $this->app->useEnvironmentPath($this->environmentPath());
+
         $this->app->singleton(
             \Illuminate\Contracts\Http\Kernel::class,
             \Roots\Acorn\Http\Kernel::class
@@ -315,6 +317,16 @@ protected function basePath(): string
         };
     }
 
+    /**
+     * Get the environment file path.
+     */
+    protected function environmentPath(): string
+    {
+        return is_file($envPath = $this->files->closest($this->basePath(), '.env'))
+            ? dirname($envPath)
+            : $this->basePath();
+    }
+
     /**
      * Use paths that are configurable by the developer.
      */
diff --git a/src/Roots/Acorn/Console/Commands/KeyGenerateCommand.php b/src/Roots/Acorn/Console/Commands/KeyGenerateCommand.php
index f6f52a81..4843dc72 100644
--- a/src/Roots/Acorn/Console/Commands/KeyGenerateCommand.php
+++ b/src/Roots/Acorn/Console/Commands/KeyGenerateCommand.php
@@ -15,9 +15,7 @@ class KeyGenerateCommand extends FoundationKeyGenerateCommand
      */
     protected function writeNewEnvironmentFileWith($key)
     {
-        $envFile = file_exists($this->laravel->environmentFilePath())
-            ? $this->laravel->environmentFilePath()
-            : File::closest($this->laravel->basePath(), '.env');
+        $envFile = $this->laravel->environmentFilePath();
 
         if (! $envFile) {
             $this->error('Unable to set application key. Create a .env file.');
@@ -25,6 +23,21 @@ protected function writeNewEnvironmentFileWith($key)
             return false;
         }
 
+        if ($this->replace($envFile, $key)) {
+            return true;
+        }
+
+        if ($this->prepend($envFile, $key)) {
+            return true;
+        }
+
+        $this->error('Unable to set application key.');
+
+        return false;
+    }
+
+    protected function replace($envFile, $key): bool
+    {
         $replaced = preg_replace(
             $this->keyReplacementPattern(),
             'APP_KEY='.$key,
@@ -32,13 +45,14 @@ protected function writeNewEnvironmentFileWith($key)
         );
 
         if ($replaced === $input || $replaced === null) {
-            $this->error('Unable to set application key. No APP_KEY variable was found in the .env file.');
-
             return false;
         }
 
-        file_put_contents($envFile, $replaced);
+        return file_put_contents($envFile, $replaced) !== false;
+    }
 
-        return true;
+    protected function prepend($envFile, $key): bool
+    {
+        return File::prepend($envFile, 'APP_KEY='.$key.PHP_EOL) !== false;
     }
 }
diff --git a/src/Roots/Acorn/Console/Kernel.php b/src/Roots/Acorn/Console/Kernel.php
index 3bf0a093..f189bd15 100644
--- a/src/Roots/Acorn/Console/Kernel.php
+++ b/src/Roots/Acorn/Console/Kernel.php
@@ -50,6 +50,7 @@ class Kernel extends FoundationConsoleKernel
      * @var string[]
      */
     protected $bootstrappers = [
+        \Illuminate\Foundation\Bootstrap\LoadEnvironmentVariables::class,
         \Roots\Acorn\Bootstrap\LoadConfiguration::class,
         \Roots\Acorn\Bootstrap\HandleExceptions::class,
         \Roots\Acorn\Bootstrap\RegisterFacades::class,
diff --git a/src/Roots/Acorn/Http/Kernel.php b/src/Roots/Acorn/Http/Kernel.php
index 983962de..3c815aa8 100644
--- a/src/Roots/Acorn/Http/Kernel.php
+++ b/src/Roots/Acorn/Http/Kernel.php
@@ -12,6 +12,7 @@ class Kernel extends HttpKernel
      * @var string[]
      */
     protected $bootstrappers = [
+        \Illuminate\Foundation\Bootstrap\LoadEnvironmentVariables::class,
         \Roots\Acorn\Bootstrap\LoadConfiguration::class,
         \Roots\Acorn\Bootstrap\HandleExceptions::class,
         \Roots\Acorn\Bootstrap\RegisterFacades::class,