diff --git a/src/Console/Commands/ProEnable.php b/src/Console/Commands/ProEnable.php
index 8d7f291a8ac..7d0650313f3 100644
--- a/src/Console/Commands/ProEnable.php
+++ b/src/Console/Commands/ProEnable.php
@@ -17,7 +17,8 @@ class ProEnable extends Command
      * @var string
      */
     protected $signature = 'statamic:pro:enable
-        { --force : Force the operation to run when in production }';
+        { --force : Force the operation to run when in production }
+        { --update-config : Also update editions config to reference .env var }';
 
     /**
      * The console command description.
@@ -37,14 +38,21 @@ public function handle()
             return;
         }
 
-        $this->laravel['config']['statamic.editions.pro'] = true;
-
         $this->checkInfo('Statamic Pro successfully enabled in .env file!');
 
-        if ($this->configNotReferencingEnv()) {
-            $this->crossLine('Statamic editions config not currently referencing .env file.');
+        if ($this->option('update-config') && $this->updateConfig()) {
+            $this->checkInfo('Statamic editions config successfully updated to reference .env var!');
+        }
+
+        if ($this->option('update-config') && ! $this->isConfigReferencingEnv()) {
+            $this->crossLine('Could not reliably update editions config to reference .env var!');
             $this->comment(PHP_EOL.'For this setting to take effect, please modify your [config/statamic/editions.php] as follows:');
             $this->line("'pro' => env('STATAMIC_PRO_ENABLED', false)");
+        } elseif (! $this->isConfigReferencingEnv()) {
+            $this->crossLine('Statamic editions config not currently referencing .env var!');
+            $this->comment('Please re-run this command with the `--update-config` option.');
+        } else {
+            $this->laravel['config']['statamic.editions.pro'] = true;
         }
     }
 
@@ -123,16 +131,46 @@ protected function envContents()
     }
 
     /**
-     * Check whether the editions config is referencing the .env var.
+     * Update editions config to reference the .env var.
      *
      * @return bool
      */
-    protected function configNotReferencingEnv()
+    protected function updateConfig()
     {
         if (! file_exists($configPath = config_path('statamic/editions.php'))) {
             return false;
         }
 
-        return ! preg_match('/[\'"]pro[\'"]\s*=>\s*env\([\'"]STATAMIC_PRO_ENABLED[\'"]/m', file_get_contents($configPath));
+        if ($this->isConfigReferencingEnv()) {
+            return false;
+        }
+
+        $contents = file_get_contents($configPath);
+
+        if (str_contains($contents, "'pro' => false,")) {
+            $contents = str_replace("'pro' => false,", "'pro' => env('STATAMIC_PRO_ENABLED', false),", $contents);
+        } elseif (str_contains($contents, "'pro' => true,")) {
+            $contents = str_replace("'pro' => true,", "'pro' => env('STATAMIC_PRO_ENABLED', false),", $contents);
+        } else {
+            return false;
+        }
+
+        file_put_contents($configPath, $contents);
+
+        return true;
+    }
+
+    /**
+     * Check whether the editions config is referencing the .env var.
+     *
+     * @return bool
+     */
+    protected function isConfigReferencingEnv()
+    {
+        if (! file_exists($configPath = config_path('statamic/editions.php'))) {
+            return true;
+        }
+
+        return (bool) preg_match('/[\'"]pro[\'"]\s*=>\s*env\([\'"]STATAMIC_PRO_ENABLED[\'"]/m', file_get_contents($configPath));
     }
 }
diff --git a/src/Statamic.php b/src/Statamic.php
index 44085ea41ff..a37c665e90b 100644
--- a/src/Statamic.php
+++ b/src/Statamic.php
@@ -5,6 +5,7 @@
 use Closure;
 use Illuminate\Http\Request;
 use Illuminate\Support\Facades\App;
+use Illuminate\Support\Facades\Artisan;
 use Illuminate\Support\Facades\Cache;
 use Illuminate\Support\Facades\Vite;
 use Laravel\Nova\Nova;
@@ -48,17 +49,7 @@ public static function pro()
 
     public static function enablePro()
     {
-        $path = config_path('statamic/editions.php');
-
-        $contents = File::get($path);
-
-        if (! Str::contains($contents, "'pro' => false,")) {
-            throw new \Exception('Could not reliably update the config file.');
-        }
-
-        $contents = str_replace("'pro' => false,", "'pro' => true,", $contents);
-
-        File::put($path, $contents);
+        Artisan::call('statamic:pro:enable', ['--update-config' => true]);
     }
 
     public static function availableScripts(Request $request)
diff --git a/tests/Console/Commands/ProEnableTest.php b/tests/Console/Commands/ProEnableTest.php
new file mode 100644
index 00000000000..308536ceda4
--- /dev/null
+++ b/tests/Console/Commands/ProEnableTest.php
@@ -0,0 +1,209 @@
+<?php
+
+namespace Tests\Console\Commands;
+
+use Illuminate\Filesystem\Filesystem;
+use Statamic\Statamic;
+use Tests\TestCase;
+
+class ProEnableTest extends TestCase
+{
+    private $files;
+    private $envPath;
+    private $editionsPath;
+    private $defaultEnvContents;
+    private $defaultEditionsContents;
+
+    public function setUp(): void
+    {
+        parent::setUp();
+
+        $this->files = app(Filesystem::class);
+
+        $this->envPath = base_path('.env');
+        $this->editionsPath = config_path('statamic/editions.php');
+
+        $this->defaultEnvContents = <<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=false
+STATAMIC_LICENSE_KEY=
+ENV;
+
+        $this->defaultEditionsContents = $this->files->get(__DIR__.'/../../../config/editions.php');
+
+        $this->files->put($this->envPath, $this->defaultEnvContents);
+
+        $this->files->makeDirectory(dirname($this->editionsPath), 0777, true, true);
+        $this->files->put($this->editionsPath, $this->defaultEditionsContents);
+    }
+
+    protected function getEnvironmentSetUp($app)
+    {
+        parent::getEnvironmentSetUp($app);
+
+        $app['config']->set('statamic.editions.pro', false);
+    }
+
+    public function tearDown(): void
+    {
+        $this->files->delete($this->envPath);
+        $this->files->delete($this->editionsPath);
+
+        parent::tearDown();
+    }
+
+    /** @test */
+    public function it_can_enable_pro_by_updating_existing_var_in_env()
+    {
+        $this->assertFalse(Statamic::pro());
+        $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
+        $this->assertEquals($this->defaultEnvContents, $this->files->get($this->envPath));
+
+        $this->artisan('statamic:pro:enable');
+
+        $this->assertTrue(Statamic::pro());
+        $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=
+ENV, $this->files->get($this->envPath));
+    }
+
+    /** @test */
+    public function it_can_enable_pro_by_appending_to_env()
+    {
+        $this->files->put($this->envPath, $this->defaultEnvContents = <<<'ENV'
+APP_NAME=Statamic
+STATAMIC_LICENSE_KEY=
+ENV);
+
+        $this->assertFalse(Statamic::pro());
+        $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
+
+        $this->artisan('statamic:pro:enable');
+
+        $this->assertTrue(Statamic::pro());
+        $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_LICENSE_KEY=
+STATAMIC_PRO_ENABLED=true
+ENV, $this->files->get($this->envPath));
+    }
+
+    /** @test */
+    public function if_config_is_not_referencing_env_var_it_should_prompt_user_to_run_with_update_config_option()
+    {
+        $this->files->put($this->editionsPath, $this->defaultEditionsContents = <<<'EDITIONS'
+<?php
+
+return [
+
+    'pro' => env('WRONG!!!', false),
+
+    'addons' => [
+        //
+    ],
+
+];
+EDITIONS);
+
+        $this->assertFalse(Statamic::pro());
+        $this->assertEquals($this->defaultEnvContents, $this->files->get($this->envPath));
+
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsOutput('Please re-run this command with the `--update-config` option.');
+
+        // Though it should still update .env
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=
+ENV, $this->files->get($this->envPath));
+
+        // Pro should not be enabled in the in-memory config, because config is not properly referencing .env var yet
+        $this->assertFalse(Statamic::pro());
+    }
+
+    public static function hardcodedBooleans()
+    {
+        return [
+            'true' => ['true'],
+            'false' => ['false'],
+        ];
+    }
+
+    /**
+     * @test
+     *
+     * @dataProvider hardcodedBooleans
+     */
+    public function it_can_update_editions_config_to_reference_env_var($boolean)
+    {
+        $this->files->put($this->editionsPath, <<<"EDITIONS"
+<?php
+
+return [
+
+    'pro' => $boolean,
+
+    'addons' => [
+        //
+    ],
+
+];
+
+EDITIONS);
+
+        $this->assertFalse(Statamic::pro());
+        $this->assertEquals($this->defaultEnvContents, $this->files->get($this->envPath));
+
+        $this->artisan('statamic:pro:enable', ['--update-config' => true]);
+
+        $this->assertTrue(Statamic::pro());
+        $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=
+ENV, $this->files->get($this->envPath));
+    }
+
+    /** @test */
+    public function if_it_has_trouble_updating_editions_config_it_should_instruct_user()
+    {
+        $this->files->put($this->editionsPath, <<<'EDITIONS'
+<?php
+
+return [
+
+    'pro' => 'wabbajack', // It should fail trying to update this!
+
+    'addons' => [
+        //
+    ],
+
+];
+EDITIONS);
+
+        $this->assertFalse(Statamic::pro());
+        $this->assertEquals($this->defaultEnvContents, $this->files->get($this->envPath));
+
+        $this
+            ->artisan('statamic:pro:enable', ['--update-config' => true])
+            ->expectsOutput(PHP_EOL.'For this setting to take effect, please modify your [config/statamic/editions.php] as follows:')
+            ->expectsOutput("'pro' => env('STATAMIC_PRO_ENABLED', false)");
+
+        // Though it should still update .env
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=
+ENV, $this->files->get($this->envPath));
+
+        // Pro should not be enabled in the in-memory config, because config is not properly referencing .env var yet
+        $this->assertFalse(Statamic::pro());
+    }
+}